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Key Largo | Islamorada | Long Key

Diving and snorkeling are the primary draws in the Upper Keys, thanks to the tropical coral reef that runs a few miles off the seaward coast. Divers of all skill levels benefit from accessible dive sites and an established tourism infrastructure. Fishing is another huge draw, especially around Islamorada, known for its sportfishing in both deep offshore waters and in the backcountry. Offshore islands accessible only by boat are popular destinations for kayakers. In short, if you don’t like the water, you might get bored here.

Other nature lovers won’t feel shortchanged. Within 1½ miles of the bay coast lie the mangrove trees and sandy shores of Everglades National Park, where naturalists lead tours of one of the world’s few saltwater forests. Here you’ll see endangered manatees, curious dolphins, and other underwater creatures. Although the number of birds has dwindled since John James Audubon captured their beauty on canvas, the rare Everglades snail kite, bald eagles, ospreys, and a colorful array of egrets and herons delight bird-watchers. At sunset, flocks take to the skies as they gather to find their night’s roost, adding a swirl of activity to an otherwise quiet time of day.

The Upper Keys are full of low-key eateries where the owner is also the chef and the food is tasty and never too fussy. The one exception is Islamorada, where you’ll find more upscale restaurants. Places to eat may close for a two- to four-week vacation during the slow season between mid-September and late October.

In the Upper Keys the accommodations are as varied as they are plentiful. The majority of lodgings are in small waterfront complexes with furnished one- or two-bedroom units. These places offer dockage and often arrange boating, diving, and fishing excursions. There are also larger resorts with every type of activity imaginable and smaller boutique hotels where the attraction is personalized service.

Depending on which way the wind blows and how close the property is to the highway, there may be some noise from Overseas Highway. If this is an annoyance for you, ask for a room as far from the traffic as possible. Some properties require two- or three-day minimum stays during holiday and high-season weekends. Conversely, discounts may apply for midweek, weekly, and monthly stays.

Getting Here and Around

Airporter operates scheduled van and bus pickup service from all Miami International Airport (MIA) baggage areas to wherever you want to go in Key Largo ($50) and Islamorada ($55). Groups of three or more passengers receive discounts. There are three departures daily; reservations are required 48 hours in advance. The SuperShuttle charges $165 to $185 for two passengers for trips from Miami International Airport to Key Largo; reservations are required. For a trip to the airport, place your request 24 hours in advance.

Contacts
Airporter. | 305/852–3413, 800/830–3413.
SuperShuttle. | 305/871–2000 | www.supershuttle.com.

Key Largo

56 miles south of Miami International Airport.

The first of the Upper Keys reachable by car, 30-mile-long Key Largo is also the largest island in the chain. Key Largo—named Cayo Largo (“Long Key”) by the Spanish—makes a great introduction to the region.

The history of Largo is similar to that of the rest of the Keys, with its succession of native people, pirates, wreckers, and developers. The first settlement on Key Largo was named Planter, back in the days of pineapple, and later, key lime plantations. For a time it was a convenient shipping port, but when the railroad arrived, Planter died on the vine. Today three communities—North Key Largo, Key Largo, and Tavernier—make up the whole of Key Largo.

If you’ve never tried diving, Key Largo is the perfect place to learn. Dozens of companies will be more than happy to show you the ropes. Nobody comes to Key Largo without visiting John Pennekamp Coral Reef State Park, one of the jewels of the state-park system. Also popular is the adjacent Key Largo National Marine Sanctuary, which encompasses about 190 square miles of coral reefs, sea grass beds, and mangrove estuaries. Both are good for underwater exploration.

Fishing is the other big draw, and world records are broken regularly. There are plenty of charter operations to help you find the big ones and teach you how to hook the elusive (but inedible) bonefish, sometimes known as the ghost fish. On land, restaurants will cook your catch or dish up their own offerings with inimitable style.

Key Largo offers all the conveniences of a major resort town, with most businesses lined up along Overseas Highway (U.S. 1), the four-lane highway that runs down the middle of the island. Cars whiz past at all hours—something to remember when you’re booking a room. Most lodgings are on the highway, so you’ll want to be as far from the road as possible.

Getting Here and Around

Key Largo is 56 miles south of Miami International Airport, with the mile markers going from 105 to 91. The island runs northeast–southwest, with Overseas Highway running down the center. If the highway is your only glimpse of the island, you’re likely to feel barraged by its tacky commercial side. Make a point of driving Route 905 in North Key Largo and down side streets to the marinas to get a better feel for it.

Visitor Information

Contact
Key Largo Chamber of Commerce. Stop in for brochures, directions, recommendations, or some colorful Key Largo T-shirts and gifts. | MM 106 BS, 10600 Overseas Hwy. | 305/451–4747, 800/822–1088 | www.keylargochamber.org.

Exploring

Dagny Johnson Key Largo Hammock Botanical State Park.
American crocodiles, mangrove cuckoos, white-crowned pigeons, Schaus swallowtail butterflies, mahogany mistletoe, wild cotton, and 100 other rare critters and plants inhabit these 2,400 acres, sandwiched between Crocodile Lake National Wildlife Refuge and Pennekamp Coral Reef State Park. The park is also a user-friendly place to explore the largest remaining stand of the vast West Indian tropical hardwood hammock and mangrove wetland that once covered most of the Keys’ upland areas. Interpretive signs describe many of the tropical tree species along a wide 1-mile paved road (2 miles round-trip) that invites walking and biking. There are also more than 6 miles of nature trails accessible to bikes and wheelchairs. Pets are welcome if on a leash no longer than 6 feet. You’ll also find restrooms, information kiosks, and picnic tables. TIP Rangers recommend not visiting when it’s raining as the trees can drip poisonous sap. | Rte. 905 OS, 0.5 mile north of Overseas Hwy. | 305/451–1202 | www.floridastateparks.org/keylargohammock | $2.50 (exact change needed) | Daily 8–sundown.

FAMILY | Dolphins Plus Bayside.
This educational program begins at the facility’s bay-side lagoon with a get-acquainted session from a platform. After that, you slip into the water for some frolicking with your new dolphin pals. Options range from a sea lion swim to a shallow-water swim with a dolphin, to a hands-on structured swim with a dolphin. You can also spend the day shadowing a trainer for a hefty $690 fee. | MM 101.9 BS, 101900 Overseas Hwy. | 305/451–4060, 877/365–2683 | www.dolphinsplus.com | $10 admission only; interactive programs from $150 | Daily 8–5.

FAMILY | Dolphins Plus Oceanside.
A sister property to Dolphins Plus Bayside, Dolphins Plus offers some of the same programs and the age requirement is lower. The cheapest option, a Natural Swim program, begins with a one-hour briefing; then you enter the water to become totally immersed in the dolphins’ world. In this visual orientation, participants snorkel but are not allowed to touch the dolphins. For tactile interaction (kissing, fin tows, etc.), sign up for the Structured Swim program, which is more expensive. | MM 99, 31 Corrine Pl. | 305/451–1993, 866/860–7946 | www.dolphinsplus.com | Programs from $165 | Daily 8–5.

FAMILY | Jacobs Aquatic Center.
Take the plunge at one of three swimming pools: an eight-lane, 25-meter lap pool with two diving boards; a 3- to 4-foot-deep pool accessible to people with mobility challenges; and an interactive children’s play pool with a waterslide, pirate ship, waterfall, and sloping zero entry instead of steps. Because so few of the motels in Key Largo have pools, it remains a popular destination for visiting families. | Key Largo Community Park, 320 Laguna Ave., at St. Croix Pl. | 305/453–7946 | www.jacobsaquaticcenter.org | $12 ($2 discount weekdays) | Daily 10–6 (10–7 in summer).

Florida Keys Wild Bird Center.
Have a nose-to-beak encounter with ospreys, hawks, herons, and other unreleasable birds at this bird rehabilitation center. The birds live in spacious screened enclosures along a boardwalk running through some of the best waterfront real estate in the Keys. Rehabilitated birds are set free, whereas about 30 have become permanent residents. Free birds—especially pelicans and egrets—come to visit every day for a free lunch from the center’s staff. A short nature trail runs into the mangrove forest (bring bug spray May to October). | MM 93.6 BS, 93600 Overseas Hwy. | Tavernier, Florida, United States | 305/852–4486 | www.keepthemflying.org | Free, donations accepted | Daily sunrise–sunset.

Beaches

FAMILY | Fodor’s Choice | John Pennekamp Coral Reef State Park.
This state park is on everyone’s list for easy access to the best diving and snorkeling in Florida. The underwater treasure encompasses 78 square miles of coral reefs and sea-grass beds. It lies adjacent to the Florida Keys National Marine Sanctuary, which contains 40 of the 52 species of coral in the Atlantic Reef System and nearly 600 varieties of fish, from the colorful parrot fish to the demure cocoa damselfish. Whatever you do, get in the water. Snorkeling and diving trips ($30 and $55, respectively, equipment extra) and glass-bottom-boat rides to the reef ($24) are available, weather permitting. One of the most popular snorkel trips is to see Christ of the Deep, the 2-ton underwater statue of Jesus. The park also has nature trails, two man-made beaches, picnic shelters, a snack bar, and a campground. Amenities: food and drink; parking (fee); showers; toilets; water sports. Best for: snorkeling; swimming. | MM 102.5 OS, 102601 Overseas Hwy. | 305/451–1202 for park, 305/451–6300 for excursions | www.pennekamppark.com, www.floridastateparks.org/pennekamp | $4.50 for 1 person in vehicle, $8 for 2–8 people, $2 for pedestrians and cyclists or extra people (plus a 50¢ per-person county surcharge) | Daily 8–sunset.

Where to Eat

Alabama Jack’s.
$ | SEAFOOD | Calories be damned—the conch fritters here are heaven on a plate. Don’t expect the traditional, golf-ball-size balls of dough; these are an unusual, mountainous freeform creation of fried, loaded-with-flavor perfection. The crab cakes, made from local blue crabs, earn hallelujahs, too. The conch salad is as good as any you’ll find in the Bahamas. This weathered, circa-1950 restaurant floats on two roadside barges in an old fishing community. Regulars include motorcyclists, families, boaters and the upscale crowd from nearby Ocean Reef Club, including Kathie Lee Gifford, who all come not only for the food but to admire tropical birds in the nearby mangroves, the occasional crocodile, and to jam with the bands playing each weekend afternoon. Dinner has to be early here; Jack’s closes by 6:30, when the mosquitoes start biting. TIP It’s about a half-hour drive from Key Largo, so you may want to plan a visit for your drive in or out. | Average main: $11 | 58000 Card Sound Rd. | 305/248–8741 | Reservations not accepted.

Ballyhoo’s.
$$$ | SEAFOOD | Occupying a 1930s Conch house with outdoor seating right alongside U.S. 1 under the seagrape trees, this local favorite is all about the fish (including the nautical decor). Yellowtail snapper, one of the moistest, most flavorful local fish, is served 10 different ways on the all-day menu, including blackened, stuffed with crab, and Parmesan-crusted. During stone-crab season (mid-October to mid-May) get in on the all-you-can-eat special. Every Friday night, locals flock for the all-you-can-eat mojo-marinated and fried-fish dinner deals. | Average main: $21 | MM 97.8 median, 97800 Overseas Hwy. | 305/852–0822 | www.ballyhoosrestaurant.com | Reservations not accepted.

Fodor’s Choice | Buzzard’s Roost Grill and Pub.
$$$ | SEAFOOD | The views are nice at this waterfront restaurant but the food is what gets your attention. Burgers, fish tacos, and seafood baskets are lunch faves. Dinner is about seafood and steaks, any way you like them. Try the smoked-fish dip, served with Armenian heart-shape lavash crackers. Look for the big signs on U.S. 1 that direct you where to turn—it’s worth finding. | Average main: $21 | Garden Cove Marina, 21 Garden Cove Dr., Northernmost Key Largo | 305/453–3746 | www.buzzardsroostkeylargo.com.

Chad’s Deli & Bakery.
$ | AMERICAN | It’s a deli! It’s a bakery! It’s a pasta place! It’s also where the locals go. By day, Chad’s serves monster sandwiches in pita wraps, rolls, or subs. It also offers pizza (try the seafood pizza with rosada sauce), pasta dishes, quesadillas, vegetarian meals, salads, burgers, and breakfast. Everyone loves the homemade soups and chowders, and there’s a good selection of beer and wine to wash it all down. Of course, you may bypass all this and make a meal out of one of Chad’s eight varieties of cookies, approximately the size of your head, including white-chocolate macadamia-nut and chocolate-chip. | Average main: $10 | MM 92.3 BS, 92330 Overseas Hwy., Tavernier | Key Largo, Florida, United States | 305/853–5566 | www.chadsdeli.com | Reservations not accepted.

The Fish House.
$$$ | SEAFOOD | Restaurants not on the water have to produce the highest quality food to survive in the Keys. That’s how the Fish House has succeeded since the 1980s—so much so that it built the Fish House Encore (a fancier version) next door to accommodate fans. The pan-sautéed catch of the day is a long-standing favorite, as is the “Matecumbe-style” preparation—baked with tomatoes, capers, olive oil, and lemon juice, it will make you moan with pleasure. Prefer shellfish? Choose from shrimp, lobster, and (mid-October to mid-May) stone crab. The smoked fish chunks are the best in the Keys. The only things bland are their side dishes: simple boiled red potatoes, a hunk of corn on the cob, or black beans and rice. For a sweet ending, the homemade key lime pie is award-winning. | Average main: $21 | MM 102.4 OS, 102341 Overseas Hwy. | 305/451–4665 | www.fishhouse.com | Reservations not accepted | Closed Sept. | American Express not accepted.

The Fish House Encore.
$$$ | SEAFOOD | To accommodate the crowds that gather at the Fish House, the owners opened this place with similar but more refined cuisine ranging from sushi to steak. It’s come into its own as a more formal dining venue than its sister establishment. In the off-season you can get your money’s worth with all-you-can-eat specials such as mahimahi, snow crab, and peel ‘n’ eat shrimp. The favorite, more casual place to dine is on the patio near the trickling fountain. Live piano music entertains Thursday through Sunday. | Average main: $27 | MM 102.3 OS, 102341 Overseas Hwy. | Key Largo, Florida, United States | 305/451–4665, 305/451–0650 | www.fishhouse.com | Reservations essential | Closed Tues. and Oct. No lunch.

Harriette’s Restaurant.
$ | AMERICAN | If you’re looking for comfort food—like melt-in-your-mouth biscuits the size of a salad plate—try this refreshing throwback. The kitchen makes muffins daily in 13 different flavors like mango, coconut, and key lime. Since the early 1980s, owner Harriette Mattson has been here to personally greet guests who come for the to-die-for omelets and old-fashioned hotcakes with sausage or bacon. For something unique, try the conch burger and eggs. At lunch, Harriette shines in the burger department, and her soups—from garlic tomato to chili—are homemade. No wonder there’s always a wait. | Average main: $8 | MM 95.7 BS, 95710 Overseas Hwy. | 305/852–8689 | Reservations not accepted | No dinner | American Express not accepted.

Jimmy Johnson’s Big Chill.
$$ | SEAFOOD | Owned by former NFL coach, Jimmy Johnson, this waterfront establishment offers three entertaining experiences, and all are big winners. You’ll find the best sports bar in the Upper Keys complete with the coach’s Super Bowl trophies, a main restaurant with all-glass indoor seating and a waterfront deck, and an enormous outdoor tiki bar with entertainment seven nights a week. There’s even a pool and cabana club where (for an entrance fee) you can spend the day sunning. Menu favorites are the Parmesan-crusted snapper and brick-oven roasted chicken wings, but don’t miss the tuna nachos—as delicious as they are artfully presented. As the sun sets over the bay, enjoy the views and a slice of key lime pie. | Average main: $16 | MM104 BS, 104000 Overseas Hwy. | 305/453–9066 | www.jjsbigchill.com.

Key Largo Conch House.
$ | AMERICAN | Tucked into the trees along the Overseas Highway, this Victorian-style home (family-owned since 2004) and its true-to-the-Keys style of cooking is worth seeking out—at least the Food Network and the Travel Channel have thought so in the past. The Old South veranda and patio seating are ideal for winter dining, but indoors the seating is tighter. Raisin pecan French toast and seven varieties of Benedicts, including conch, are brunch favorites. Lunch and dinner menus cover all bases, from a conch chowder bread bowl and vegetarian wraps to lobster and conch ceviche. Lionfish is proudly served when available, as is local yellowtail snapper. Interesting fact: the restaurant’s “loo” was voted “Best of” for local restaurants. | Average main: $15 | MM 100.2,100211 Overseas Hwy. | Key Largo, Florida, United States | 305/453–4844 | www.keylargoconchhouse.com | Reservations essential.

Mrs. Mac’s Kitchen.
$ | SEAFOOD | Townies pack the counters and booths at this tiny eatery, where license plates are stuck on the walls and made into chandeliers, for everything from blackened prime rib to crab cakes. Every night is themed including Meatloaf Monday, Italian Wednesday, and Seafood Sensation (offered Friday and Saturday). There’s also a Champagne breakfast (at this original location) and an assortment of tasty Angus beef burgers, sandwiches, a famous chili, and key lime freeze (a tangy concoction somewhere between a shake and a float). In season, ask about the hogfish special du jour. A second location, Mrs. Mac’s Kitchen 2, is half a mile south on the Overseas Highway (99020 Overseas Hwy., MM99 Center), also in Key Largo. The newer location offers a similar menu, a full bar, and double the seating, but the original rules supreme on food. | Average main: $15 | MM 99.4 BS, 99336 Overseas Hwy. | 305/451–3722, 305/451–6227 | www.mrsmacskitchen.com | Closed Sun.

Snapper’s.
$ | SEAFOOD | “You hook ‘em, we cook ‘em” is the motto here. Alas, “cleanin’ ‘em” is not part of the bargain. If you bring in your ready-for-the-grill fish, dinner here is $14 for a single, $15 per person family style with a mix of preparations. Otherwise, they’ll catch and prepare you a plank-roasted yellowtail snapper, Thai-seared tuna, fish of the day baked with 36 herbs and spices, or a little something from the raw bar. The ceviche of yellowtail, shrimp, and conch (merrily spiced) wins raves, too. The seafood burrito on the sandwich board is a keeper. All this is served up in a lively, mangrove-ringed waterfront setting with live music, an aquarium bar, Sunday brunch (including a build-your-own Bloody Mary bar), killer rum drinks, and seating alongside the fishing dock. | Average main: $15 | MM 94.5 OS, 139 Seaside Ave. | 305/852–5956 | www.snapperskeylargo.com | Reservations not accepted.

Sundowners.
$$$ | AMERICAN | The name doesn’t lie. If it’s a clear night and you can snag a reservation, this restaurant will treat you to a sherbet-hue sunset over Florida Bay. If you’re here in mild weather—anytime other than the dog days of summer or the rare winter cold snap—the best seats are on the patio. The food is excellent: try the key lime seafood, a happy combo of sautéed shrimp, lobster, and lump crabmeat swimming in a tangy sauce spiked with Tabasco served over penne or rice. Wednesday and Saturday are all about prime rib, and Friday draws the crowds with an all-you-can-eat fish fry. Vegetarian and gluten-free options are available. To beat the crowds, stop in for lunch, which offers the same great food, minus the hassle. | Average main: $22 | MM 104 BS, 103900 Overseas Hwy. | 305/451–4502 | sundownerskeylargo.com | Reservations essential.

Where to Stay

Amy Slate’s Amoray Dive Resort.
$ | RESORT | You can read this hotel’s name either as “a moray” (referring to the moray eels you’ll encounter on the reef) or “amore” (Italian for love, which calls to mind the place’s romantic atmosphere), and you’ll understand the place’s dual charms. One- and two-story clapboard cottages huddle around the property’s marina and sandy beach. A PADI-certified dive facility, it’s a great place to rent equipment or take courses. Unlike many other resorts, single rooms are available. Pros: top-notch dive operation; free use of snorkel equipment. Cons: noise from highway; minimum stays during peak times. | Rooms from: $159 | MM 104.2 BS, 104250 Overseas Hwy. | Key Largo, Florida, United States | 305/451–3595, 800/426–6729 | www.amoray.com | 23 rooms, 8 apartments | No meals.

Azul del Mar.
$$ | B&B/INN | The dock points the way to many beautiful sunsets at this no-smoking, adults-only boutique hotel, which Karol Marsden (an ad exec) and her husband Dominic (a travel photographer) have transformed from a run-down mom-and-pop place into a waterfront gem. As you’d expect from innkeepers with a background in the image business, the property offers great visuals, from marble floors and granite countertops to yellow-leather sofas and ice-blue bathroom tiles. Kayaks, barbecue grills, and a movie library are available for guest use, and two chickee huts on the beach are equipped with comfortable seating. Pros: great garden; good location; sophisticated design. Cons: small beach; high-priced; minimum stays during holidays. | Rooms from: $299 | MM 104.3 BS, 104300 Overseas Hwy. | 305/451–0337, 888/253–2985 | www.azulkeylargo.com | 2 studios, 3 1-bedroom suites, 1 2-bedroom suite | No meals.

Coconut Bay Resort & Bay Harbor Lodge.
$ | RESORT | Some 200 feet of waterfront is the main attraction at these side-by-side sister properties that offer a choice between smaller rooms and larger separate cottages. Coconut palms whisper in the breeze and gumbo-limbo trees shade the 2½-acre grounds. Nice features abound, like well-placed lounge chairs for gazing out over the water, and kayaks and paddleboats (for when you want to get closer). Everybody shows up on the sundeck or the 16-foot dock to watch the sun slip into Davy Jones’s Locker. The rooms are a bit tight but not without island character. Pale-yellow cottages are simply furnished. Ask for Unit 25 and 26, a two-bedroom villa that will give you extra space and a water view. Pros: bay front; neatly kept gardens; walking distance to restaurants; free use of kayaks, paddleboat, and paddleboards. Cons: a bit dated; small sea-walled sand beach. | Rooms from: $175 | MM 97.7 BS, 97702 Overseas Hwy. | 305/852–1625, 800/385–0986 | www.coconutbaykeylargo.com | 7 rooms, 5 efficiencies, 2 suites, 1 2-bedroom villa, 6 1-bedroom cottages | Breakfast.

Coconut Palm Inn.
$$ | B&B/INN | You’d never find this waterfront haven unless someone told you it was there, as it’s tucked into a residential neighborhood beneath towering palms and native gumbo limbos. No wonder it’s a favorite of travel magazines. Each unit overlooks part of the 400-foot beach, where draping hammocks beckon you to nap. Prefer to paddleboard or kayak? Just slide one off the sand and go. Or take a dip in the pool. Less adventurous types can head for the Adirondack chairs along the shoreline or to those placed at the far end of the docks that jet into the bay. Units are comfortable, spacious, and could be the backdrop for a Tommy Bahama ad with their upscale, tropical decor and hand-carved furniture. Small patios give you your own slice of paradise. Breakfast is served beneath the bay-front chickee. Pros: secluded; quiet; sophisticated feel. Cons: front desk closes early each evening; no access to ice machine when staff leaves; breakfast is ho-hum. | Rooms from: $299 | MM 92 BS, 198 Harborview Dr., via Jo-Jean Way off Overseas Hwy. | Tavernier | 305/852–3017 | www.coconutpalminn.com | 13 rooms, 7 suites | Breakfast.

Dove Creek Lodge.
$$ | B&B/INN | With its sherbet-hue rooms and plantation-style furnishings, these tropical-style units (19 in all) range in size from simple lodge rooms to luxury two-bedroom suites. Best of all, they’re surprisingly plush, and many have a private screened porch or balcony. This is a favorite among travelers to Key Largo, and fishermen especially love the easy access to the water. You can head out on a boat from the marina, chase billfish offshore, or try for bonefish on the flats. Pros: luxurious rooms; walk to Snapper’s restaurant; complimentary kayaks and Wi-Fi. Cons: no beach; some find the music from next door bothersome. | Rooms from: $269 | MM 94.5 OS, 147 Seaside Ave. | 305/852–6200, 800/401–0057 | www.dovecreeklodge.com | 11 rooms, 8 suites | Breakfast.

Fodor’s Choice | Hilton Key Largo Resort.
$$ | RESORT | Nestled within a hardwood hammock (localese for uplands habitat where hardwood trees such as live oak grow) near the southern border of Everglades National Park, this sprawling resort had a $12-million renovation in 2012 and offers a full slate of amenities in a woodsy setting. Spacious guest rooms with pillow-top mattresses include a balcony, and nature trails and boardwalks lead to a private, white-sand beach. Your explorations will also reveal two outdoor heated pools, two restaurants, awesome water sports, and stunning sunset views. Pros: nice nature trail on bay side; pretty pools with waterfalls; awesome trees; bicycles available for rent. Cons: some rooms overlook the parking lot; pools near the highway; expensive per-night resort fee. | Rooms from: $259 | MM 97 BS, 97000 Overseas Hwy. | 305/852–5553, 888/871–3437 | www.keylargoresort.com | 190 rooms, 10 suites | No meals.

Island Bay Resort.
$$ | RENTAL | When Mike and Carol Shipley took over this off-the-beaten-path resort in 2000, they revamped the 10 bay-side cottages, improved the landscaping, and added touches such as hammocks and Adirondack chairs that make you feel like this is your own personal tropical playground. It offers a definitive “I’ve escaped to the Keys!” satisfaction. However, this is a quiet resort, so if you’re looking to party, you won’t find that here. Three room types (efficiencies, one-bedroom, and two-bedroom units) are offered, each with its own theme according to its name (Sunset, Floral, Boats, Islamorada, etc.). All have updated baths, tiled floors, sponge-painted walls, and thoughtful decor. Pros: on the water; sunset views. Cons: most units are small; no pool; lacks on-site amenities. | Rooms from: $249 | 92530 Overseas Hwy. | 305/852-4087 | www.islandbayresort.com | 10 units | No meals.

Jules’ Undersea Lodge.
$$$$ | HOTEL | You can truly sleep with the fishes at this underwater inn. The former research lab has two rooms that sit 5 fathoms (30 feet) below the surface, letting you watch the undersea world through three 42-inch porthole windows. This isn’t the place if you’re claustrophobic (each of the two rooms is a very cozy 8 by 10 feet), value your privacy (you share a kitchen and bathroom with the other guests), or can’t swim (the only way to gain access to the lodge is by strapping on scuba gear), but it is the place if you want to brag about unique accommodations when you get home. You must either be a certified diver or take the hotel’s three-hour introductory course (an additional $95). Rates include breakfast and pizza dinner (the latter delivered to your door) and the unlimited use of diving gear. Because of the length of time you’ll spend underwater, you can’t fly for 24 hours after checking out. The office is open 8–2 weekdays, 8–4 weekends. New is an opportunity to visit the lodge without spending the night; the three-hour experience includes a pizza lunch and costs $150 per-person, two-person minimum. Pros: one-of-a-kind experience; unbeatable views. Cons: must be a certified diver or take the special course to stay here; tight accommodations. | Rooms from: $800 | MM 103.2 OS, 51 Shoreland Dr. | 305/451–2353 | www.jul.com | 2 rooms | Some meals.

Fodor’s Choice | Kona Kai Resort, Gallery & Botanic Gardens.
$$ | RESORT | Brilliantly colored bougainvillea, coconut palm, and guava trees—and a botanical garden of other rare species—make this 2-acre adult hideaway one of the prettiest places to stay in the Keys. Each of the intimate cottages has furnishings that add to the tropical feel. Spacious studios and one- and two-bedroom suites—with full kitchens and original art—are filled with natural light. Outside, kick back in a lounge chair or hammock, soak in the hot tub, or contemplate sunset from the deck. The resort also has an art gallery and an orchid house with more than 225 plants. At the pool, help yourself to complimentary bottled water and fruit. Pros: free custom tours of botanical gardens for guests; free use of sports equipment; knowledgeable staff. Cons: expensive; some rooms are very close together. | Rooms from: $289 | MM 97.8 BS, 97802 Overseas Hwy. | 305/852–7200, 800/365–7829 | www.konakairesort.com | 8 suites, 5 rooms | No meals.

FAMILY | Marriott’s Key Largo Bay Beach Resort.
$$$ | RESORT | This 17-acre bayside resort has plenty of diversions, from diving to parasailing to a day spa. Given all that, the pool still rules, so a stroll to the tiki bar could well be your most vigorous activity of the day. The resort’s lemon-yellow facade exudes an air of warm, indolent days. This isn’t the poshest chain hotel you’ve ever encountered, but it’s fresh looking and suitably tropical in style. Some of the best rooms and suites offer sunset views. Yes, they have a beach, but like most beaches in the Keys, it’s not very exciting. Pros: lots of activities; free covered parking; dive shop on property; free Wi-Fi. Cons: rooms facing highway can be noisy; thin walls. | Rooms from: $359 | MM 103.8 BS, 103800 Overseas Hwy. | 305/453–0000, 866/849–3753 | www.marriottkeylargo.com | 132 rooms, 20 2-bedroom suites, 1 penthouse suite | No meals.

The Pelican.
$ | HOTEL | This 1950s throwback is reminiscent of the days when parents packed the kids into the station wagon and headed to no-frills seaside motels, complete with old-fashioned fishing off the dock. The owners have spiffed things up with cute, artsy touches and added a small sunning beach, but basically it’s just a motel, not fancy but comfortable. Guests here don’t mind skimping on space and a few frills in favor of homey digs, socializing under the chickee, and a reasonable price tag. Pros: free use of kayaks and a canoe; well-maintained dock; reasonable rates. Cons: some small rooms; basic accommodations and amenities. | Rooms from: $150 | MM 99.3, 99340 Overseas Hwy. | 305/451–3576, 877/451–3576 | www.hungrypelican.com | 13 rooms, 4 efficiencies, 4 suites | Breakfast.

Popp’s Motel.
$ | HOTEL | Stylized metal herons mark the entrance to this 50-year-old family-run motel. The third and fourth generations of the Popp family are currently at the helm, taking care of the basic-but-clean units. Don’t be discouraged by the building clutter around the office. Inside the rooms bright paint jobs, shiny terrazzo floors, and modern kitchens contrast. Room 9 is closest to the beach. Pros: beach; intimate feel; multiple night discounts. Cons: limited amenities; worn, outdated interiors. | Rooms from: $149 | MM 95.5 BS, 95500 Overseas Hwy. | Key Largo, Florida, United States | 305/852–5201, 877/852–5201 | www.popps.com | 9 units | No meals.

Seafarer Resort and Beach.
$ | HOTEL | It’s very basic budget lodging, but the Seafarer Resort is not without its charms including draping bougainvillea and stately gumbo limbos. There’s a pond and hammocks; many rooms have water views, and some have private patios. Rooms 3, 4, and 5 are spacious and best for families. Unit 6, a one-bedroom cottage called the “beach house,” has a large picture window with an awesome view of the bay. Each unit has its own charcoal grill and outdoor seating, and at sunset, guests gather at the private beach and dock for sunset-watching. Pros: sandy beach; complimentary kayak use; cheap rates. Cons: some rooms close to road noise; some complaints about cleanliness. | Rooms from: $139 | MM 97.6 BS, 97684 Overseas Hwy. | Key Largo, Florida, United States | 305/852–5349 | www.seafarerkeylargo.com | 8 rooms, 3 studios, 1 1-bedroom cottage, 1 2-bedroom cottage, 2 apartments | No meals.

Nightlife

The semiweekly Keynoter (Wednesday and Saturday), weekly Reporter (Thursday), and Friday through Sunday editions of the Miami Herald are the best sources of information on entertainment and nightlife. Daiquiri bars, tiki huts, and seaside shacks pretty well summarize Key Largo’s bar scene.

Breezers Tiki Bar & Grille.
Mingle with locals over cocktails and sunsets at Marriott’s Key Largo Bay Beach Resort. | Marriott Key Largo Bay Beach Resort, 103800 Overseas Hwy. | 305/453–0000.

Caribbean Club.
Walls plastered with Bogart memorabilia remind customers that the classic 1948 Bogart–Bacall flick Key Largo has a connection with this worn watering hole. Although no food is served and the floors are bare concrete, this landmark draws boaters, curious visitors, and local barflies to its humble bar stools and pool tables. But the real magic is around back, where you can grab a seat on the deck and catch a postcard-perfect sunset. Live music draws revelers Thursday through Sunday. | MM 104 BS, 10404 Overseas Hwy. | 305/451–4466.

Shopping

For the most part, shopping is sporadic in Key Largo, with a couple of shopping centers and fewer galleries than you find on the other big islands. If you’re looking to buy scuba or snorkeling equipment, you’ll have plenty of places from which to choose.

Gumbo Limbo Pottery.
Here you’ll find functional and decorative ceramics ranging from signature lanterns and porcelain kitchenware to one-of-a-kind high-fire sculptures where the owners’ creative talent at the wheel blazes. It’s no coincidence that their creations will remind you of the sky, land, and sea of the Florida Keys. | MM 102.9 OS, 102991 Overseas Hwy. | 305/741–7108 | www.gumbolimbopottery.com | Closed Tues.

Gallery at Kona Kai.
If you haven’t been here lately, get here. In addition to original works by major international artists—including sea captain–turned-painter Dirk Verdoorn —this gallery at the Kona Kai Resort has added revolving exhibits relating to plants, botanicals and the environment. It’s the ideal introduction to the on-site botanic gardens—another must-see. | MM 97.8 BS, 97802 Overseas Hwy. | Key Largo, Florida, United States | 305/852–7200 | www.g-k-k.com.

Fodor’s Choice | Key Largo Chocolates.
Specializing in key lime truffles made with quality Belgian chocolate, this is the only chocolate factory in the entire Florida Keys. But you’ll find much more than just the finest white, milk, and dark chocolate truffles; try their cupcakes, ice cream, and famous “chocodiles.” Another fan favorite is the salted turtles, which are worth every calorie. Chocolate classes are also available for kids and adults, and a small gift area showcases local art, jewelry, hot sauces, and other goodies. Look for the bright green-and-pink building. | MM100 BS, 100471 Overseas Hwy. | 305/453–6613 | www.keylargochocolates.com.

Key Lime Products.
Go into olfactory overload—you’ll find yourself sniffing every single bar of soap and scented candle inside this key lime treasure trove. Take home some key lime juice (supereasy pie-making directions are right on the bottle), marmalade, candies, sauces, even key lime shampoo. Outside, you’ll find a huge selection of wood carvings, pottery, unique patio furniture, and artwork. They’re even grilling up fresh fish sandwiches that alone are worth the stop. | MM 95.2 BS, 95231 Overseas Hwy. | Key Largo, Florida, United States | 305/853–0378, 800/870–1780 | www.keylimeproducts.com.

Randy’s Florida Keys Gift Co.
Since 1989, Randy’s has been “the” place for unique gifts. Owner Randy and his wife Lisa aren’t only fantastic at stocking the store with a plethora of items, they’re well respected in the community for their generosity and dedication. Stop in and say hello then browse the tight aisles and loaded shelves filled with key lime candles, books, wood carvings, jewelry, clothing, T-shirts, and eclectic, tropical decor items. This friendly shop prides itself on carrying wares from local craftsmen and there’s something for every budget. | 102421 Overseas Hwy. | Right on U.S. 1, next to Sandal Factory Outlet | 305/453–9229 | www.keysmermaid.com.

Shell World.
You can find lots of shops in the Keys that sell cheesy souvenirs—snow globes, alligator hats, and shell-encrusted anything. This is the granddaddy of them all. But this sprawling building in the median of Overseas Highway has much more than shell lamps and snow globes, you’ll find high-end clothing, jewelry, housewares, artwork, and a wide selection of eclectic souvenirs from delightfully tacky to tasteful. | MM 97.5,97600 Overseas Hwy. | 305/852–8245, 888/398–6233 | www.shellworldflkeys.com.

Sports and the Outdoors

Biking

Not as big a pursuit as on other islands, biking can be a little dangerous along Key Largo’s main drag. Parts of the still-developing Florida Keys Overseas Heritage Trail take you off Highway 1 along Old Highway.

Bubba’s.
Bubba’s organizes one-week custom biking tours through the Keys along the heritage trail. A van accompanies tours to carry luggage and tired riders. Former police officer Bubba Barron also hosts an annual one-week ride down the length of the Keys every November. Riders can opt for tent camping ($735) or motel-room accommodations. Meals are included, but bike rentals are extra. | Key Largo, Florida, United States | 321/759–3433 | www.bubbaspamperedpedalers.com | From $735.

Boating

Everglades Eco-Tours.
Captain Sterling operates Everglades and Florida Bay ecology tours and more expensive sunset cruises. You can see dolphins, manatees, and birds from the casual comfort of his pontoon boat, equipped with PVC chairs. Bring your own food and drinks. | MM 104 BS, Sundowners Restaurant, 103900 Overseas Hwy. | 305/853–5161, 888/224–6044 | www.captainsterling.com | From $59.

M.V.
Key Largo Princess.
Two-hour glass-bottom-boat trips and sunset cruises on a luxury 70-foot motor yacht with a 280-square-foot glass viewing area depart from the Holiday Inn docks three times a day. | Holiday Inn, MM 100 OS, 99701 Overseas Hwy. | 305/451–4655, 877/648–8129 | www.keylargoprincess.com | $35.

Canoeing and Kayaking

Sea kayaking continues to gain popularity in the Keys. You can paddle for a few hours or the whole day, on your own or with a guide. Some outfitters even offer overnight trips. The Florida Keys Paddling Trail, part of a statewide system, runs from Key Largo to Key West. You can paddle the entire distance, 110 miles on the Atlantic side, which takes 9–10 days. The trail also runs the chain’s length on the bay side, which is a longer route.

Coral Reef Park Co.
At John Pennekamp Coral Reef State Park, this operator has a fleet of canoes and kayaks for gliding around the 2½-mile mangrove trail or along the coast. Powerboat rentals are also available. | MM 102.5 OS, 102601 Overseas Hwy. | 305/451–6300 | www.pennekamppark.com | Rentals from $12 per hr.

Florida Bay Outfitters.
Rent canoes or sea kayaks from this company, which sets up self-guided trips on the Florida Keys Paddling Trail, helps with trip planning, and matches equipment to your skill level. It also runs myriad guided tours around Key Largo. Take a full-moon paddle or a one- to seven-day kayak tour to the Everglades, Lignumvitae Key, or Indian Key. | MM 104 BS, 104050 Overseas Hwy. | 305/451–3018 | www.paddlefloridakeys.com | From $15.

Fishing

Private charters and big head boats (so named because they charge “by the head”) are great for anglers who don’t have their own vessel.

Sailors Choice.
Fishing excursions depart twice-daily (half-day trips are cash-only), but the company also does private charters. The 65-foot boat leaves from the Holiday Inn docks. Rods, bait, and license are included. | Holiday Inn Resort & Marina, MM 100 OS, 99701 Overseas Hwy. | 305/451–1802, 305/451–0041 | www.sailorschoicefishingboat.com | From $40.

Scuba Diving and Snorkeling

Much of what makes the Upper Keys a singular dive destination is variety. Places like Molasses Reef, which begins 3 feet below the surface and descends to 55 feet, have something for everyone, from novice snorkelers to experienced divers. The Spiegel Grove, a 510-foot vessel, lies in 130 feet of water, but its upper regions are only 60 feet below the surface. On rough days, Key Largo Undersea Park’s Emerald Lagoon is a popular spot. Expect to pay about $80 for a two-tank, two-site dive trip with tanks and weights, or $35–$40 for a two-site snorkel outing. Get big discounts by booking multiple trips.

Amy Slate’s Amoray Dive Resort.
This outfit makes diving easy. Stroll down to the full-service dive shop (NAUI, PADI, TDI, and BSAC certified), then onto a 45-foot catamaran. Certification courses are also offered. | MM 104.2 BS, 104250 Overseas Hwy. | 305/451–3595, 800/426–6729 | www.amoray.com | From $85.

Conch Republic Divers.
Book diving instruction as well as scuba and snorkeling tours of all the wrecks and reefs of the Upper Keys. Two-location dives are the standard, and you’ll pay an extra $15 for tank and weights. | MM 90.8 BS, 90800 Overseas Hwy. | 305/852–1655, 800/274–3483 | www.conchrepublicdivers.com | From $70.

Coral Reef Park Co.
At John Pennekamp Coral Reef State Park, this company gives 3½-hour scuba and 2½-hour snorkeling tours of the park. In addition to the great location and the dependability it’s also suited for water adventurers of all levels. | MM 102.5 OS, 102601 Overseas Hwy. | 305/451–6300 | www.pennekamppark.com | From $30.

Horizon Divers.
The company has customized diving and snorkeling trips that depart daily aboard a 45-foot catamaran. | 100 Ocean Dr., No. 1 | Key Largo, Florida, United States | 305/453–3535, 800/984–3483 | www.horizondivers.com | From $50 for snorkeling from $80 for diving.

Island Ventures.
This operator provides daily excursions that take you snorkeling or scuba diving. Scuba trips, offered twice daily, include tanks and weights; snorkeling trips are also offered, and ride-alongs pay just $40. | Jules Undersea Lodge, 51 Shoreland Dr. | Key Largo, Florida, United States | 305/451–4957 | www.islandventure.com | Snorkel trips $50, diving $85.

Keys Diver & Snorkel Center.
This operator offers snorkel and dive trips that take you to Florida Keys National Marine Sanctuary. For two-tank dives, choose shallow reefs or deep wrecks; snorkel excursions are also offered with two or three stops. A new offering is a night dive in a bioluminiscent bay. | MM 99.6 BS, 99696 Overseas Hwy. | Key Largo, Florida, United States | 305/451–1177 | www.keysdiver.com | Snorkel trips from $29.95, dive trips from $78.95.

Ocean Divers.
The PADI five-star facility has been around since 1975 and offers day and night dives, a range of courses, and dive-lodging packages. Two-tank reef dives include tank and weight rental. There are also organized snorkeling trips with equipment. | MM 100 OS, 522 Caribbean Dr. | 305/451–1113, 800/451–1113 | www.oceandivers.com | Snorkel trips from $35, diving from $85.

Fodor’s Choice | Quiescence Diving Services.
This operator sets itself apart in two ways: it limits groups to six to ensure personal attention and offers both two-dive day and night dives, as well as twilight dives when sea creatures are most active. There are also organized snorkeling excursions. | MM 103.5 BS, 103680 Overseas Hwy. | 305/451–2440 | www.quiescence.com | Snorkel trips $49, diving from $69.

Islamorada

Islamorada is between mile markers 90.5 and 70.

Early settlers named this key after their schooner, Island Home, but to make it sound more romantic they translated it into Spanish: Isla Morada. The chamber of commerce prefers to use its literal translation “Purple Island,” which refers either to a purple-shelled snail that once inhabited these shores or to the brilliantly colored orchids and bougainvilleas.

Early maps show Islamorada as encompassing only Upper Matecumbe Key. But the incorporated “Village of Islands” is made up of a string of islands that the Overseas Highway crosses, including Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, Craig Key, and Fiesta Key. In addition, two state-park islands accessible only by boat—Indian Key and Lignumvitae Key—belong to the group.

Islamorada (locals pronounce it eye-la-mor-ah-da) is one of the world’s top sportfishing destinations. For nearly 100 years, seasoned anglers have fished these clear, warm waters teeming with trophy-worthy fish. There are numerous options for those in search of the big ones, including chartering a boat with its own crew or heading out on a vessel rented from one of the plethora of marinas along this 20-mile stretch of the Overseas Highway. Islamorada is one of the more affluent resort areas of the Keys. Sophisticated resorts and restaurants meet the needs of those in search of luxury, but there’s also plenty for those looking for something more casual and affordable. Art galleries and boutiques make Islamorada’s shopping scene the best in the Upper Keys, but if you’re shopping for groceries, head to Marathon or Key Largo.

Essentials

Visitor Information
Islamorada Chamber of Commerce & Visitors Center. | MM 87.1 BS, 87100 Overseas Hwy. | 305/664–4503, 800/322–5397 | www.islamoradachamber.com.

Exploring

Florida Keys Memorial / Hurricane Monument.
On Monday, September 2, 1935, more than 400 people perished when the most intense hurricane to make landfall in the United States swept through this area of the Keys. Two years later, the Florida Keys Memorial was dedicated in their honor. Native coral rock, known as keystone, covers the 18-foot obelisk monument that marks the remains of more than 300 storm victims. A sculpted plaque of bending palms and waves graces the front (although many are bothered that the palms are bending in the wrong direction). In 1995, the memorial was placed on the National Register of Historic Places. | MM 81.5, OS, 81000 Overseas Hwy. | Free.

History of Diving Museum.
Adding to the region’s reputation for world-class diving, this museum plunges into the history of man’s thirst for undersea exploration. Among its 13 galleries of interactive and other interesting displays are a submarine and helmet re-created from the film 20,000 Leagues Under the Sea. Vintage U.S. Navy equipment, diving helmets from around the world, and early scuba gear explore 4,000 years of diving history. For the grand finale, spend $3 for a mouthpiece and sing your favorite tune at the helium bar. There are extended hours (until 7 pm) on the third Wednesday of every month. | MM 83 BS, 82990 Overseas Hwy., Upper Matecumbe Key | 305/664–9737 | www.divingmuseum.org | $12 | Daily 10–5.

Islamorada Founder’s Park.
This public park is the gem of Islamorada and boasts a palm-shaded beach, swimming pool, marina, skate park, tennis, and plenty of other facilities. If you want to rent a boat or learn to sail, businesses here can help you. If you’re staying in Islamorada, admission is free. Those staying elsewhere pay $8 to enter the park. Either way, you pay an additional $3 to use the Olympic-size pool. A spiffy amphitheater hosts concerts, plays, and shows. The shallow water beach is ideal for swimming and families with little ones. Showers and bathrooms are beachside. | MM 87 BS, 87000 Overseas Hwy. | 305/853–1685.

FAMILY | Robbie’s Marina.
Huge, prehistoric-looking denizens of the not-so-deep, silver-sided tarpon congregate around the docks at this marina on Lower Matecumbe Key. Children—and lots of adults—pay $3 for a bucket of sardines to feed them and $1 each for dock admission. Spend some time hanging out at this authentic Keys community, where you can grab a bite to eat indoors or out, shop at a slew of artisans’ booths, or charter a boat, kayak, or other watercraft. | MM 77.5 BS, 77522 Overseas Hwy., Lower Matecumbe Key | 305/664–9814, 877/664–8498 | www.robbies.com | Dock access $1 | Daily sunrise–sunset.

FAMILY | Theater of the Sea.
The second-oldest marine-mammal center in the world doesn’t attempt to compete with more modern, more expensive parks. Even so, it’s among the better attractions north of Key West, especially if you have kids in tow. In addition to marine life exhibits and shows, you can make reservations for up-close-and-personal encounters like a swim with a dolphin or sea lion, or stingray and turtle feedings (which include general admission; reservations required). These are popular, so reserve in advance. Ride a “bottomless” boat to see what’s below the waves and take a guided tour of the marine-life exhibits. Nonstop animal shows highlight conservation issues. You can stop for lunch at the grill, shop in the extensive gift shop, or sunbathe and swim at their private beach. This easily could be an all-day attraction. | MM 84.5 OS, 84721 Overseas Hwy., Windley Key | 305/664–2431 | www.theaterofthesea.com | $31.95; interaction programs $35–$185 | Daily 9:30–5 (last ticket sold at 3:30).

Upper Matecumbe Key.
This was one of the first of the Upper Keys to be permanently settled. Early homesteaders were so successful at growing pineapples in the rocky soil that at one time the island yielded the country’s largest annual crop. However, foreign competition and the hurricane of 1935 killed the industry. Today, life centers on fishing and tourism, and the island is filled with everything from bait shops and charter boats to eclectic galleries and fusion restaurants. | MM 84–79.

Off the Beaten Path: Indian Key Historic State Park.
Mystery surrounds 10-acre Indian Key, on the ocean side of the Matecumbe islands. Before it became one of the first European settlements outside of Key West, it was inhabited by American Indians for several thousand years. The islet served as a base for 19th-century shipwreck salvagers until an Indian attack wiped out the settlement in 1840. Dr. Henry Perrine, a noted botanist, was killed in the raid. Today his plants grow in the town’s ruins. Most people kayak or canoe here from Indian Key Fill or take a boat from Robbie’s Marina to tour the nature trails and the town ruins or to snorkel. There are no restrooms or picnic facilities on Indian Key. | Islamorada | 305/664–2540 park | www.floridastateparks.org/indiankey | Free | Daily 8–5.

Off the Beaten Path: Lignumvitae Key Botanical State Park.
On the National Register of Historic Places, this 280-acre bay-side island is the site of a virgin hardwood forest and the 1919 home of chemical magnate William Matheson. His caretaker’s cottage serves as the park’s visitor center. Access is by boat—your own, a rented vessel, or a tour operated from Robbie’s Marina. The tour leaves at 8:30 am Friday through Sunday and takes in both Lignumvitae and Indian keys (reservations required). Paddling here from Indian Key Fill, at MM 78.5, is a popular pastime. The only way to do the trails is by a guided ranger walk, offered at 10 am and 2 pm Friday to Sunday. Wear long sleeves and pants, and bring mosquito repellent. On the first Saturday in December is the Lignumvitae Christmas Celebration, when the historic home is decorated 1930s-style. | Islamorada | 305/664–2540 park, 305/664–8070 boat tours | www.floridastateparks.org/lignumvitaekey | $2.50; $35 for boat tours | Park Thurs.–Mon. 8–5; house tours Fri.–Sun. at 10 and 2.

Windley Key.
This is the highest point in the Keys, though at 16 feet above sea level it’s not likely to give anyone altitude sickness. Originally two islets, this area was first inhabited by American Indians, who left behind a few traces of their dwellings, and then by farmers and fishermen who built their homes here in the mid-1800s. Henry Flagler bought the land from homesteaders in 1908 for his Florida East Coast Railway, filling in the inlet between what were then called the Umbrella Keys. His workers quarried coral rock for the rail bed and bridge approaches—the same rock used in many historic South Florida structures, including Miami’s Vizcaya and the Hurricane Monument on Upper Matecumbe. Although the Quarry Station was destroyed by the 1935 hurricane, quarrying continued until the 1960s. Today, this is where you’ll find Theater of the Sea, the famous Holiday Isle (now Postcard Inn), and Windley Key Fossil Reef Geological State Park. | MM 86–84 | Islamorada, Florida, United States.

Windley Key Fossil Reef Geological State Park.
The fossilized-coral reef, dating back about 125,000 years, demonstrates that the Florida Keys were once beneath the ocean. Excavation of Windley Key’s limestone bed by the Florida East Coast Railway exposed the petrified reef, full of beautifully fossilized brain coral and sea ferns. Visitors can see the fossils along a 300-foot quarry wall when hiking the park’s three trails. There are guided (Friday, Saturday, and Sunday only) and self-guided tours along the trails, which lead to the railway’s old quarrying equipment and cutting pits, where you can make rubbings of the quarry walls. The Alison Fahrer Environmental Education Center holds historic, biological, and geological displays about the area, including videos. The first Saturday in March is Windley Key Day, when the park sells native plants and hosts environmental exhibits. | MM 84.9 BS, Windley Key | 305/664–2540 | www.floridastateparks.org/windleykey | $2.50; additional $2 for guided tours (self-guided is free) | Education center Fri.–Sun. 9–5 (tours at 10 and 2).

Beaches

Anne’s Beach Park.
On Lower Matecumbe Key this popular village park is named for a local environmental activist. Its “beach” (really a typical Keys-style sand flat with a gentle slope) is best enjoyed at low tide. The nicest feature here is an elevated, wooden half-mile boardwalk that meanders through a natural wetland hammock. Covered picnic areas along the way give you places to linger and enjoy the view. Restrooms are at the north end. Weekends are packed with Miami day-trippers as it’s the only public beach until you reach Marathon. Amenities: parking (no fee); toilets. Best for: partiers; snorkeling; swimming; windsurfing. | MM 73.5 OS, Lower Matecumbe Key | 305/853–1685.

Where to Eat

Fodor’s Choice | Chef Michael’s.
$$$ | SEAFOOD | Peace. Love. Hogfish. That’s the motto of this local favorite that’s been making big waves since its opening in 2011 with Chef Michael Ledwith at the helm. Sit outdoors on the covered wood deck and tap your toes to the live music, or dine inside amid dark wood floors and white linens. Seafood is selected fresh daily, then elegantly prepared with a splash of tropical flair. Try hogfish with mango sauce, or the catch “Juliette” with shrimp, scallops, Chardonnay butter, and toasted almonds. Carnivores can feast on prime-grade beef, carved in-house—with the kind of marbling that just melts in your mouth. Chef Michael even grows his own herbs, right outside the kitchen door. How about a watermelon mint sangria? Just say yes. Gluten-free and vegetarian dishes are available. | Average main: $29 | MM81.7, 81671 Overseas Hwy, Upper Matecumbe Key | 305/664–0640 | www.foodtotalkabout.com | Reservations essential | No lunch Mon.–Sat.

Green Turtle Inn.
$$$ | SEAFOOD | This circa-1947 landmark inn and its vintage neon sign is a slice of Florida Keys history. Period photographs decorate the wood-paneled walls. Breakfast options include surprises like French toast made with challah bread and Captain Morgan batter, and Keys Benedict with a blue crab cake. For lunch, skip the fish dip, and opt for lobster mac and cheese. Turtle chowder (don’t gasp; it’s made from farm-raised, freshwater turtles) is a staple. For dessert, the seventh-generation pound cake gets a standing ovation. | Average main: $24 | MM 81.2 OS, 81219 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–2006 | www.greenturtlekeys.com | Reservations essential | Closed Mon.

Hungry Tarpon.
$$ | SEAFOOD | As part of the colorful, bustling Old Florida scene at Robbie’s Marina, you know that the seafood here is fresh and top quality. The extensive menu seems as if it’s bigger than the dining space, which consists of a few tables and counter-seating indoors, plus tables out back under the mangrove trees, close to where tourists pay to feed the tarpon in the marina. While tarpon are snacking on sardines, diners enjoy quite the impressive smattering of dishes for breakfast, lunch, and dinner. Specialties include biscuits and gravy, cracked conch, a Matecumbe fish sandwich with provolone and bacon on grilled sourdough, and a shrimp burrito. | Average main: $19 | MM 77.5 BS, 77522 Overseas Hwy., Lower Matecumbe Key | 305/664–0535 | www.hungrytarpon.com | Reservations not accepted.

FAMILY | Islamorada Fish Company.
$$ | SEAFOOD | When a restaurant is owned by Bass Pro Shops, you know the seafood should be as fresh as you can get it. The fun begins in the parking lot with painted white fish marking the parking spaces. The restaurant is housed in an open-air, oversized tiki hut right on Florida Bay, making this the quintessential Keys experience. There’s a small, low-key tiki bar area if you prefer a stool to a table. Menu highlights include cracked conch beaten ‘til tender and fried crispy, and Grouper Portofino, which will keep you coming back for more. Each afternoon, the staff feed the fish in the bay. Jump out of your seat and walk over for a close-up view of snapper, large tarpon, and even sharks. | Average main: $18 | MM 81.5 BS, 81532 Overseas Hwy., Windley Key | 305/664–9271 | restaurants.basspro.com/fishcompany/Islamorada/ | Daily 11–10.

Island Grill.
$ | SEAFOOD | Don’t be fooled by appearances; this shack on the waterfront takes island breakfast, lunch, and dinner up a notch. The eclectic menu tempts you with such dishes as its famed “original tuna nachos,” lobster rolls, and a nice selection of seafood and sandwiches. Southern-style shrimp and andouille sausage with grits join island-style specialties such as grilled ribs with guava barbecue sauce on the list of entrées. There’s an air-conditioned dining room and bar as well as open seating under a vaulted porch ceiling. The outdoor bar hosts live entertainment Wednesday to Sunday. Don’t be in a hurry; service is usually slow. | Average main: $14 | MM 85.5 OS, 85501 Overseas Hwy., Windley Key | Islamorada, Florida, United States | 305/664–8400 | www.keysislandgrill.com | Reservations not accepted.

Kaiyo Grill & Sushi.
$$$ | JAPANESE | The decor—an inviting setting that includes colorful abstract mosaics, polished wood floors, and upholstered banquettes—almost steals the show at Kaiyo, but the food is equally interesting. The menu, a fusion of East and West, offers sushi rolls that combine local ingredients with traditional Japanese tastes. A wood grill is used to prepare such dishes as grilled catch-of-the-day and hardwood grilled rack of lamb. Drunken scallops are a must. Wine and sake choices are abundant, and the manager is a sommelier, so take advantage of his expertise and try pairings customized to your liking. | Average main: $28 | MM 81.5 OS, 81701 Overseas Hwy., Upper Matecumbe Key | 305/664–5556 | www.kaiyogrill.com | Reservations essential | No lunch.

Lorelei Restaurant & Cabana Bar.
$ | AMERICAN | Local anglers gather here for breakfast. Lunch and dinner bring a mix of islanders and visitors for straightforward food and front row seats to the sunset. Live music seven nights a week ensures a lively nighttime scene, and the menu staves off inebriation with burgers, barbecued baby back ribs, and Parmesan-crusted snapper. Key lime pie comes frozen with mango sauce. Service can be less than stellar and the gathering at sunset is always crowded. | Average main: $15 | MM 82 BS, 81924 Overseas Hwy., Upper Matecumbe Key | 305/664–2692 | www.loreleicabanabar.com | Reservations not accepted.

Marker 88.
$$$$ | SEAFOOD | A few yards from Florida Bay, this seafood restaurant has been popular since the late ‘60s. Large picture windows offer great sunset views, but the bay is lovely no matter what time of day you visit. Outdoor dining is popular, too. Chef Bobby Stoky serves such irresistible entrées as onion-crusted mahimahi, crispy yellowtail snapper, and house-smoked seasalt-and-black-pepper-encrusted rib eye. In addition, there are a half dozen burgers and sandwiches, and you can’t miss the restaurant’s famous key lime baked Alaska dessert. The extensive wine list is an oenophile’s delight. | Average main: $34 | MM 88 BS, 88000 Overseas Hwy., Plantation Key | 305/852–9315 | www.marker88.info | Reservations essential.

FAMILY | Morada Bay Beach Café.
$$$ | ECLECTIC | This bay-front restaurant wins high marks for its surprisingly stellar cuisine, tables planted in the sand, and tiki torches that bathe the evening in romance. Entrées feature alluring combinations like fresh fish of the day sautéed with Meyer lemon butter and whole fried snapper with coconut rice. Seafood takes center stage, but you can always get roasted organic chicken or prime rib. Tapas and raw bar menus cater to smaller appetites or those who can’t decide, with offerings like fried calamari, conch fritters, and Wagyu beef sliders. Lunch adds interesting sandwiches to the mix. Sit in a dining room outfitted with surfboards, or outdoors on a beach, where the sunset puts on a mighty show and kids (and your feet) play in the sand. | Average main: $27 | MM 81 BS, 81600 Overseas Hwy., Upper Matecumbe Key | 305/664–0604 | www.moradabay-restaurant.com.

Fodor’s Choice | Pierre’s.
$$$$ | FRENCH | One of the Keys’ most elegant restaurants, Pierre’s marries colonial style with modern food trends. Full of interesting architectural artifacts, the place oozes style, especially the wicker chair–strewn veranda overlooking the bay. Save your best “tropical chic” duds for dinner here, so you don’t stand out from your surroundings. The food, drawn from French and Floridian influences, is multilayered and beautifully presented. Among the seasonally changing appetizer choices, you might find smoked hogfish chowder and foie gras sliders with a butternut squash milk shake. A changing list of entrées might include hogfish meunière and scallops with pork belly tortellini. The downstairs bar is a perfect spot for catching sunsets, sipping martinis, and enjoying light eats. | Average main: $40 | MM 81.5 BS, 81600 Overseas Hwy., Upper Matecumbe Key | 305/664–3225 | www.moradabay.com | Reservations essential | No lunch.

Where to Stay

Fodor’s Choice | Casa Morada.
$$ | B&B/INN | This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor showers and Jacuzzis in some of the suites. Each unit claims its own design personality, many with an Asian feel. Lush landscaping, a pool surrounded by a sandy “beach” on its own island accessible by a bridge, and lounge chairs at the water’s edge lend a spalike vibe; complimentary yoga classes, a Zen garden, and a rock grotto complete the scene. Cool tile-and-terrazzo floors invite you to kick off your shoes and step out onto your private patio overlooking the gardens and the bay. Breakfast and lunch are served on the waterside terrace. Pros: cool design; complimentary snacks and bottled water; complimentary use of bikes, kayaks, and snorkel gear. Cons: trailer park across the street; beach is small and inconsequential. | Rooms from: $299 | MM 82 BS, 136 Madeira Rd., Upper Matecumbe Key | 305/664–0044, 888/881–3030 | www.casamorada.com | 16 suites | Breakfast.

Fodor’s Choice | Cheeca Lodge & Spa.
$$ | RESORT | At 27 acres, this may be the largest resort in the Keys, and it’s also big on included amenities. In the main lodge, West Indies–style rooms boast luxurious touches like elegant soaking tubs that fill in a stream from the ceiling. If soaking in a tub isn’t your thing, soak up the great views from the glass, floor-to-ceiling showers. The main building also holds three oceanfront restaurants including a sushi bar, and an outdoor swimming pool keeps the party going with underwater speakers and a tiki bar. The resort’s other buildings hold more styles of accommodations and a spa with a bevy of signature treatments including hot lava shell massages, an adults-only lap pool with a bar, and a fitness center. For families, there’s the 1,200-foot private beach, kayaks, bikes, fishing rods, a walking trail, and Camp Cheeca—a fun and educational program for kids 5–12. Golf (nine holes), tennis, and all manner of water sports cater to sports enthusiasts. At night, tiki torches light up paths and add even more ambience, if that’s possible. Pros: beautifully landscaped grounds; new designer rooms; water-sports center on property. Cons: expensive rates; expensive resort fee; very busy. | Rooms from: $299 | MM 82 OS, Upper Matecumbe Key | 305/664–4651, 800/327–2888 | www.cheeca.com | 60 1-bedroom suites, 64 junior suites | No meals.

Chesapeake Beach Resort.
$ | RESORT | This boutique hotel on the beach mixes modern conveniences with a retro look. High-tech gadgets like flat-screen TVs, CD players, and MP3 players give the place an up-to-date feel. Coral stone and dark wood accent the rooms, each of which has a porch or a balcony. Most units are lined up along the long stretch of sand that all but encircles a lagoon; others overlook the tennis court. Room service is available only from 11:30 am to 9:30 pm. Pros: oceanfront location; free use of water-sports equipment and Wi-Fi (included in resort fee). Cons: dated exterior; mandatory resort fee (per room per night). | Rooms from: $199 | MM 83.5, 83409 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–4662, 800/338–3395 | www.chesapeake-resort.com | 44 rooms, 8 suites, 13 villas | Breakfast.

Drop Anchor Resort and Marina.
$ | HOTEL | Immaculately maintained, this place has the feel of an old friend’s beach house. And it’s easy to find your unit here, as they are painted in an array of Crayola colors. Inside you’ll find soothing West Indies–type furnishings and kitschy-cool, 1950s-era tile in the bathrooms. Welcoming as the rooms may be, you didn’t come to the Keys to sit indoors: there’s a luscious expanse of white sand awaiting, and you can catch ocean breezes from either your balcony, a comfy Adirondack chair, or a picnic table perched in the sand. There’s a boat ramp to accommodate anglers. Pros: bright and colorful; attention to detail; laid-back charm. Cons: noise from the highway; beach is better for fishing than swimming. | Rooms from: $149 | MM 85 OS, 84959 Overseas Hwy., Windley Key | 305/664–4863, 888/664–4863 | www.dropanchorresort.com | 18 suites | No meals.

The Islander, A Guy Harvey Outpost Resort.
$$ | RESORT | Guests here get to choose between a self-sufficient town home on the bay with room for a boat, or an oceanfront resort with on-site restaurants and oodles of amenities. Such decisions. Either way, the interiors are bright and casual, with a touch of Guy Harvey style. Oceanside, private, screened porches lead to a coral-shell beach. Families snap up suites in the oceanfront Beach House; couples looking for more privacy head to rooms set back from the beach. The pools—one saltwater, one freshwater—win raves, as do the full kitchens. A 200-foot dock, lighted at night, plus shuffleboard, basketball, and volleyball add to the resort feel. Guy’s Beachside Bar & Grill offers an oceanside meal, and the new Discovery Center boasts state-of-the-art exhibits. Pros: spacious rooms; nice kitchens; eye-popping views. Cons: pricey for what you get; beach has rough sand. | Rooms from: $249 | MM 82.1 OS, 82200 Overseas Hwy., Upper Matecumbe Key | 305/664–2031, 800/753–6002 | www.guyharveyoutpostislamorada.com | 114 rooms, 12 suites, 25 townhomes | Breakfast.

Fodor’s Choice | The Moorings Village.
$$$$ | HOTEL | This tropical retreat is everything you imagine when you think of the Keys—from hammocks swaying between towering trees to sugar-white sand (arguably the Keys’ best resort beach) lapped by aqua-green waves. West Indies–style cottages with cypress and Dade County pine accents, colorful shutters, private verandas, and wicker furniture sit in a canopy of coconut palms and old forest landscaping on a residential street off the highway. This is a high-end slice of Old Florida, so don’t expect tacky tiki bars. The one-, two-, and three-bedroom cottages all have modern kitchens with modern appliances. A palm-lined walkway leads to the beach, where a swimming dock awaits. The spa offers massages (in the beach chickee, if you desire) and beauty treatments. During busy season, there may be one-week minimum. Neighboring Cheeca Lodge, the Moorings has the same high standards but is less cramped, more private and exclusive, and possibly the most beautiful property in the Keys. Pros: romantic setting; good dining options with room-charging privileges; beautiful beach. Cons: no room service; $20 daily resort fee for activities. | Rooms from: $529 | MM 81.6 OS, 123 Beach Rd., Upper Matecumbe Key | 305/664–4708 | www.themooringsvillage.com | 18 cottages | No meals.

Fodor’s Choice | Ocean House.
$$$ | HOTEL | Islamorada’s newest adult boutique hotel is situated right on the Atlantic, yet it’s hidden from passersby amid lush gardens. Whether you stay on the first or second floor, each of the luxurious suites (with names like Saltwater Taffy, Sandbar, Dolphin, and Coral Reef) offer elegant tropical decor, comfortable furnishings, a full-size refrigerator, private outdoor terrace, granite tiled shower, and flat-screen TV. Guests rave over the saltwater infinity pool, flowing cabanas, private beach, beachside fire pit, and complimentary continental breakfast served in suite. This is one of the few places where you can experience Zayak sea sleds. Pros: complimentary use of kayaks, snorkel equipment and bicycles; luxurious facilities and amenities. Cons: limited number of units means they’re often booked solid; luxury comes at a price. | Rooms from: $319 | MM 82 OS, 82885 Old Hwy., Windley Key | 866/540–5520 | www.oceanhousefloridakeys.com | 8 suites | Some meals.

Postcard Inn Beach Resort & Marina at Holiday Isle.
$$ | RESORT | After an $11-million renovation that encompassed updating everything from the rooms to the public spaces, this iconic property (formerly known as the Holiday Isle Beach Resort) has found new life. Units are “boathouse chic” in style, with white wood accents, faux-wood-tiled floors, and a comfy daybed for lounging. A nice touch are the stenciled quotes from ocean lovers, for ocean lovers. If you like keeping busy, their marina offers fishing charters, diving and snorkeling trips. Or check out their water-sport rentals and the famous “Holiday Isle Tiki Bar.” Pros: large private beach; heated pools; on-site restaurants including Shula’s 2. Cons: rooms near tiki bar are noisy; minimum stay required during peak times; bathrooms need updating. | Rooms from: $215 | MM 84 OS, 84001 Overseas Hwy., Plantation Key | 305/664–2321 | www.holidayisle.com | 143 rooms | No meals.

FAMILY | Ragged Edge Resort.
$ | HOTEL | Nicely tucked away in a residential area at the ocean’s edge, this family-owned hotel draws returning guests who’d rather fish off the dock and grill up dinner than loll around in Egyptian cotton sheets. Even those who turn their noses up at the plastic deck furniture and pine paneling admit that the place has a million-dollar setting, with fabulous ocean views. There’s no beach, but you can bike across the street to Founder’s Park, where you’ll find one with water toys for rent. Some declare the rooms plain-Jane, but they’re clean and spacious, and the bathrooms have been nicely updated. A large grassy area is perfect for kids to play while waiting for manatees to make an appearance at the marina. Ground-floor units have screened porches; upper units have large decks, more windows, and beam ceilings. Pros: oceanfront; boat docks and ramp; cheap rates. Cons: dated decor; off the beaten path. | Rooms from: $169 | MM 86.5 OS, 243 Treasure Harbor Rd., Plantation Key | 305/852–5389, 800/436–2023 | www.ragged-edge.com | 6 studios, 1 efficiency, 3 2-bedroom suites | No meals.

Nightlife

Islamorada isn’t known for its raging nightlife, but for local fun Lorelei’s and the Postcard Inn are legendary. Others cater to the town’s sophisticated clientele and fishing fervor.

Hog Heaven.
Come by boat or car to this oceanfront restaurant and sports bar where you can soak in the views dockside or relax in the air-conditioning. Munch on fresh fish sandwiches or barbecue dishes while you shoot pool, catch the big game on large flat screens, or dance to a live band or DJ. Late night can get a bit wild and loud. | MM 85.3 OS, 85361 Overseas Hwy. | Islamorada, Florida, United States | 305/664–9669 | www.hogheavensportsbar.com.

Lorelei Restaurant & Cabana Bar.
Behind a larger-than-life mermaid, this is the kind of place you fantasize about during those long cold winters up north. It’s all about good drinks, tasty pub grub, and beautiful sunsets set to live bands playing island tunes and light rock nightly. Dining is all outdoors, on a deck or under the trees. Service is slow, sometime even nonexistent. | MM 82 BS, 81924 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–2692 | www.loreleicabanabar.com.

Safari Lounge.
Locals often refer to Safari Lounge as the Dead Animal Bar, or simply DAB, because of the mounted big-game trophies lining the walls and ceiling. Within eyeshot of the sea, it’s a good spot to hoist a few with the island drinking crowd. Happy hour daily 5–7. | MM 73.5 OS, 73814 Overseas Hwy. | Islamorada, Florida, United States | 305/664–8142.

Zane Grey Long Key Lounge.
Above the World Wide Sportsman, Zane Grey Long Key Lounge was created to honor writer Zane Grey, one of the most famous members of the Long Key Fishing Club. The lounge displays the author’s photographs, books, and memorabilia. Listen to live blues, jazz, and Motown on a wide veranda that invites sunset watching. Full menu available. | MM 81.5 BS, 81576 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–4615 | restaurants.basspro.com/ZaneGreyLounge.

Ziggie & Mad Dog’s.
The area’s glam celebrity hangout, Ziggie & Mad Dog’s serves appetizers with its happy-hour drink specials. Its wine list and outrageous steaks have become legendary. | MM 83 BS, 83000 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–3391 | www.ziggieandmaddogs.com.

Shopping

Art galleries, upscale gift shops, and the mammoth World Wide Sportsman (if you want to look the part of a local fisherman, you must wear a shirt from here) make up the variety and superior style of Islamorada shopping.

Banyan Tree.
Stroll and shop among the colorful orchids and lush plants at this outdoor garden and indoor boutique known for its tropical splendor, unique gifts and free-spirited clothing. There is nothing quite like it in the area. | MM 81.2 OS, 81197 Overseas Hwy., Upper Matecumbe Key | 305/664–3433 | www.banyantreegarden.com | Closed Sun.

Casa Mar Village.
Change is good, and in this case, it’s fantastic. What was once a row of worn-down buildings is now a merry blend of gift shops and galleries with the added bonus of a place selling fresh-roasted coffee. By day, these colorful shops glisten at their canalfront location, by nightfall, they’re lit up like a lovely Christmas town. The offerings include the Jolly Pelican, Casa Mar Seafood, and the Fresh Press Cafe. | MM90 OS, 90775 Old Hwy., Upper Matecumbe Key | 305/522–0330 | www.casamarvillage.com.

Gallery Morada.
This gallery is a go-to destination for one-of-a-kind gifts, beautifully displayed blown glass, original sculptures, paintings, and jewelry by 200 artists. Its location, front and center, makes it the gateway to the Morada Way Arts and Cultural District, an area with artist galleries, shops, potters, gardens, and culinary classes. | MM 81.6 OS, 81611 Old Hwy., Upper Matecumbe Key | 305/664–3650 | www.gallerymorada.com.

Hooked on Books.
Among the best buys in town are the used best sellers at this bookstore, which also sells new titles, audiobooks, and CDs. Their Florida book collection is noteworthy. | MM 81.9 OS, 81909 Overseas Hwy., Upper Matecumbe Key | 305/517–2602 | www.hookedonbooksfloridakeys.com.

Island Silver & Spice.
This upscale shop is the place to go for women’s and men’s resort wear, fine tropical jewelry, and high-end watches. Island-themed glassware and elegant kitchen items make excellent gifts. Upstairs is unique tropical home decor, as well as the clearance section. | MM 82 OS, 81981 Overseas Hwy., Upper Matecumbe Key | 305/664–2714.

Rain Barrel Artisan Village.
This is a natural and unhurried shopping showplace. Set in a tropical garden of shady trees, native shrubs, and orchids, the crafts village has shops selling the work of local and national artists as well as resident artists who sell work from their own studios. Have your photo taken with “Betsy,” the giant Florida lobster, roadside. | MM 86.7 BS, 86700 Overseas Hwy., Plantation Key | 305/852–3084 | www.seefloridaonline.com/rainbarrel/index.html.

Redbone Gallery.
One of the largest sportfishing–art galleries in Florida stocks hand-stitched clothing and giftware, in addition to work by wood and bronze sculptors such as Kendall van Sant; watercolorist C.D. Clarke; and painters Daniel Caldwell, David Hall, Steven Left, and Stacie Krupa. Proceeds benefit cystic fibrosis research. Find them in the Morada Way Arts & Cultural District. | MM 81.5 OS, 200 Morada Way, Upper Matecumbe Key | 305/664–2002 | www.redbone.org.

World Wide Sportsman.
This two-level retail center sells upscale and everyday fishing equipment, resort clothing, sportfishing art, and other gifts. When you’re tired of shopping, relax at the Zane Grey Long Key Lounge, located above the store—but not before you step up and into Pilar, a replica of Hemingway’s boat. | MM 81.5 BS, 81576 Overseas Hwy., Upper Matecumbe Key | 305/664–4615, 800/327–2880.

Sports and the Outdoors

Boating

Marinas pop up every mile or so in the Islamorada area, so finding a rental or tour is no problem. Robbie’s Boat Rentals & Charters is a prime example of a salty spot where you can find it all—from fishing charters and kayaking rentals to lunch and tarpon feeding.

Bump & Jump.
You can rent both fishing and deck boats here (from 15 to 29 feet) by the day or the week. Free local delivery with seven-day rentals from each of their locations. | MM 85.9 BS, 85920 Overseas Hwy., Upper Matecumbe Key | 305/664–9404, 877/453–9463 | www.keysboatrental.com | Rentals from $165 per day.

Houseboat Vacations of the Florida Keys.
See the islands from the comfort of your own boat (captain’s cap optional). The company maintains a fleet of 44- to 55-foot boats that accommodate up to 10 people and come outfitted with everything you need besides food. (You may provision yourself at a nearby grocery store.) There’s a three-day minimum; weekly rates are available. Kayaks, paddleboards, and dinghys suitable for bay side use also available. | MM 85.9 BS, 85944 Overseas Hwy. | 305/664–4009 | www.baysidetikiboats.com | From $1,350.

Nauti-Limo.
Captain Joe Fox has converted the design of a 1983 pink Caddy stretch limo into a less-than-luxurious but certainly curious watercraft. The seaworthy hybrid—complete with wheels—can sail with the top down if you’re in the mood. Only in the Keys! One-hour and longer tours are available. | Lorelei Restaurant & Yacht Club, MM 82 BS, 96 Madeira Rd., Upper Matecumbe Key | Islamorada, Florida, United States | 305/942–3793 | www.nautilimo.com | From $60.

Robbie’s Boat Rentals & Charters.
This full-service company will even give you a crash course on how not to crash your boat. The rental fleet includes an 18-foot skiff with a 90-horsepower outboard to a 21-foot deck boat with a 130-horsepower engine. Robbie’s also rents snorkeling gear (there’s good snorkeling nearby) and sells bait, drinks, and snacks. Want to hire a guide who knows the local waters and where the fish lurk? Robbie’s offers offshore-fishing trips, patch-reef trips, and party-boat fishing. Backcountry flats trips are a specialty. | MM 77.5 BS, 77522 Overseas Hwy., Lower Matecumbe Key | 305/664–9814, 877/664–8498 | www.robbies.com | From $185 per day.

Treasure Harbor Marine.
The Anderson family will provide everything you need for a bareboat sailing vacation at sea. They also give excellent advice on where to find the best anchorages, snorkeling spots, or lobstering sites. Vessels range from a 23.5-foot Hunter to a 41-foot Morgan Out Island. Boats can be rented by the day or week. Marina facilities include water, electric, laundry, picnic tables, and restrooms with showers. Transient and long-term dockage available. | MM 86.5 OS, 200 Treasure Harbor Dr., Plantation Key | 305/852–2458, 800/352–2628 | www.treasureharbor.com | From $175 per day.

Fishing

Here in the self-proclaimed “sportfishing capital of the world,” sailfish is the prime catch in the winter and dolphinfish (mahimahi) in the summer. Buchanan Bank just south of Islamorada is a good spot to try for tarpon in the spring. Blackfin tuna and amberjack are generally plentiful in the area, too. TIP The Hump at Islamorada ranks highest among anglers’ favorite fishing spots in Florida because of the incredible offshore marine life.

Captain Ted Wilson.
Go into the backcountry for bonefish, tarpon, redfish, snook, and shark aboard a 17-foot boat that accommodates up to three anglers. Two people can choose three-quarter or full-day trips, two-hour sunset bonefishing excursions, or evening fishing excursions. There’s an extra $100 charge for each additional person. | MM 79.9 OS, 79851 Overseas Hwy., Upper Matecumbe Key | 305/942–5224, 305/664–9463 | www.captaintedwilson.com | Bonefishing from $250, 3/4-day trips from $500.

Florida Keys Fly Fish.
Like other top fly-fishing and light-tackle guides, Captain Geoff Colmes helps his clients land trophy fish in the waters around the Keys. | 105 Palm La., Upper Matecumbe Key | 305/853–0741 | www.floridakeysflyfish.com | From $550.

Florida Keys Outfitters.
Long before fly-fishing became popular, Sandy Moret was fishing the Keys for bonefish, tarpon, and redfish. Now he attracts anglers from around the world on a quest for the big catch. His weekend fly-fishing classes include classroom instruction, equipment, and daily lunch. Guided fishing trips can be done for a half day or full day. Packages combining fishing and accommodations at Islander Resort are available. | MM 81.2, Green Turtle, 81219 Overseas Hwy., Upper Matecumbe Key | 305/664–5423 | www.floridakeysoutfitters.com | Half-day trips from $495.

Hubba Hubba Charters.
Captain Ken Knudsen has fished the Keys waters since the 1970s. A licensed backcountry guide, he’s ranked among Florida’s top 10 by national fishing magazines. He offers four-hour sunset trips for tarpon and two-hour sunset trips for bonefish, as well as half- and full-day outings. Prices are for one or two anglers, and tackle and bait are included. | MM 79.8 OS, Upper Matecumbe Key | 305/664–9281 | From $200.

Miss Islamorada.
This 65-foot party boat offers full-day trips. Bring your lunch or buy one from the dockside deli. | Bud n’ Mary’s Marina, MM 79.8 OS, 79851 Overseas Hwy., Upper Matecumbe Key | 305/664–2461, 800/742–7945 | www.budnmarys.com | From $65.

Scuba Diving and Snorkeling

San Pedro Underwater Archaeological Preserve State Park.
About 1¼ nautical miles south of Indian Key is the San Pedro Underwater Archaeological Preserve State Park, which includes the remains of a Spanish treasure-fleet ship that sank in 1733. The state of Florida protects the site for divers; no spearfishing or souvenir collecting is allowed. Seven replica cannons and a plaque enhance what basically amounts to a 90-foot-long pile of ballast stones. Resting in only 18 feet of water, its ruins are visible to snorkelers as well as divers and attract a colorful array of fish. | MM 85.5 OS | 305/664–2540 | www.floridastateparks.org/sanpedro.

Florida Keys Dive Center.
Dive from John Pennekamp Coral Reef State Park to Alligator Light with this outfitter. The center has two 46-foot Coast Guard–approved dive boats, offers scuba training, and is one of the few Keys dive centers to offer Nitrox and Trimix (mixed gas) diving. | MM 90.5 OS, 90451 Overseas Hwy., Plantation Key | 305/852–4599, 800/433–8946 | www.floridakeysdivectr.com | Snorkeling from $38, diving from $65.

Islamorada Dive Center.
This one-stop dive shop has a resort, pool, restaurant, lessons, and twice-daily dive and snorkel trips. You can take a day trip with a two-tank dive or a one-tank night trip with their equipment or yours. Snorkel and spearfishing trips are also available. | MM 84 OS, 84001 Overseas Hwy., Windley Key | 305/664–3483, 800/327–7070 | www.islamoradadivecenter.com | Snorkel trips from $45, diving from $80.

Tennis

Islamorada Tennis Club.
Not all Keys recreation is on the water. Play tennis year-round at a well-run facility with four clay and two hard courts (all lighted), same-day racket stringing, ball machines, private lessons, and a full-service pro shop. | MM 76.8 BS, 76800 Overseas Hwy., Upper Matecumbe Key | Islamorada, Florida, United States | 305/664–5341 | www.islamoradatennisclub.net | From $25.

Water Sports

The Kayak Shack.
You can rent kayaks for trips to Indian (about 20 minutes one-way) and Lignumvitae (about 45 minutes one way) keys, two favorite destinations for paddlers. Kayaks can be rented for a half day (and you’ll need plenty of time to explore those mangrove canopies). Pedal kayaks are also available and are a bit more expensive. The company also offers guided three-hour tours, including a snorkel trip to Indian Key. It also rents stand-up paddleboards, including instruction, and canoes. | Robbie’s Marina, MM 77.5 BS, 77522 Overseas Hwy., Lower Matecumbe Key | 305/664–4878 | www.kayakthefloridakeys.com | From $40 for single, $55 for double; guided trips from $45.

Long Key

Long Key is between mile markers 70 and 65.5

Long Key isn’t a tourist hot spot, making it a favorite destination for those looking to avoid the masses and enjoy some ecological history in the process.

Getting Here and Around

Long Key has the tiny town of Layton at its heart. Many people get around by bike.

Exploring

Long Key State Park.
Come here for solitude, hiking, fishing, and camping. On the ocean side, the Golden Orb Trail leads to a boardwalk that cuts through the mangroves (may require some wading) and alongside a lagoon where waterfowl congregate (as do mosquitoes, so be prepared). A 1¼-mile canoe trail leads through a tidal lagoon, and a broad expanse of shallow grass flats is perfect for bonefishing. Bring a mask and snorkel to observe the marine life in the shallow water. The park is particularly popular with campers who long to stake their tent at the campground on a beach. In summer, no-see-ums (biting sand flies) also love the beach, so again—be prepared. The picnic area is on the water, too, but lacks a beach. Canoes rent for $10 per day, and kayak rentals start at $17.50 for a single for two hours, $21.50 for a double. Rangers lead tours every Wednesday and Thursday at 10 on birding, boating, or beachcombing. | MM 67.5 OS, 67400 Overseas Hwy. | 305/664–4815 | www.floridastateparks.org/longkey | $4.50 for 1 person, $5.50 for 2 people, and 50¢ for each additional person in the group | Daily 8–sunset.

Layton Nature Trail.
Up the road 0.6 mile from Long Key State Park, beginning at a close-to-the-ground marker, is a free trail that leads through a tropical-hardwood forest to a rocky Florida Bay shoreline overlooking shallow grass flats. It takes about 20 minutes to walk the 0.25-mile trail. | MM 67.7 BS | Long Key, Florida, United States.

Beaches

Long Key State Park Beach.
Camping, snorkeling, and bonefishing are the favored activities along this narrow strip of natural, rocky shoreline and its shallow, seagrass-bottom waters. It lines the park’s campground, which is open only to registered campers. While the campground is open only to registered campers, the “day” area offers a nice respite, although those expecting a wide, sandy beach will be thoroughly disappointed. If you’re seeking a spot by the shoreline, this could be your place in the sun. Amenities: showers; toilets. Best for: snorkeling; swimming; walking. | MM 67.5 OS, 67400 Overseas Hwy. | Long Key, Florida, United States | 305/664–4815 | www.floridastateparks.org/longkey | $4.50 for 1 person, $5.50 for 2 people, and 50¢ for each additional person in the group | Daily 8–sunset.

Where to Stay

Lime Tree Bay Resort.
$ | RESORT | Easy on the eye and the wallet, this 2½-acre resort on Florida Bay offers simple accommodations that are far from the hustle and bustle of the larger islands. Walls are painted in faux finishes and display tropical art. The five apartments offer stunning gulf views, while four deluxe rooms have cathedral ceilings. Six two-bedroom master suites, steps from the gulf, have been added. Most units have a shared balcony or porch. Hammocks and chickee huts dot the 100-palm property. Free kayaks and Wi-Fi are available to all guests. Pros: great views; friendly staff; close to Long Key State Park. Cons: no restaurants nearby; shared balconies; gravel beach. | Rooms from: $199 | MM 68.5 BS, 68500 Overseas Hwy. | Layton | 305/664–4740, 800/723–4519 | www.limetreebayresort.com | 10 rooms, 10 studios, 4 2-bedroom suites, 20 minisuites, 4 efficiencies | Breakfast.

En Route: Long Key Viaduct.
As you cross Long Key Channel, look beside you at the old viaduct. The second-longest bridge on the former rail line, this 2-mile-long structure has 222 reinforced-concrete arches. The old bridge is popular with cyclists and anglers, who fish off the sides day and night. | Long Key.

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