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Day 1: Naples

Fly into Naples’s Aeroporto Capodichino, a scant 8 km (5 miles) from the city. Naples is rough around the edges and may be a bit jarring if you’re a first-time visitor, but it’s classic Italy, and most visitors end up falling in love with the city’s alluring waterfront palazzi and spectacular pizza. First things first, though: recharge with a nap and, after that, a good caffè—Naples has some of the world’s best. Revive in time for an evening stroll down Naples’s wonderful shopping street, Via Toledo, to Piazza Plebescito, before dinner and bed.

Logistics: Under no circumstances should you rent a car for Naples. Take a taxi from the airport—it’s not far, or overly expensive—and you should face few logistical obstacles on your first day in Italy.

Day 2: Naples

Start the day at the Museo Archaeologico Nazionale, budgeting at least two hours for the collection. Then take Via Santa Maria di Costantinopoli and grab a coffee at one of the outdoor cafés in Piazza Bellini. From here, head down Via dei Tribunali for a pizza at I Decumani or Di Matteo. Continue along Tribunali to Via del Duomo for a visit to the city’s cathedral. From Via del Duomo, turn right onto Spaccanapoli, turning off for a brief stop at the Cappella Sansevero for a look at the pinnacle of Masonic sculpture before heading to Piazza del Gesù and the churches of Il Gesù Nuovo and Santa Chiara. Walk downhill, following the Via Monteoliveto and Via Medina to the harbor and the Castel Nuovo; then head past the Teatro San Carlo to the enormous Palazzo Reale. Walk 15 minutes south to the Castel dell’Ovo in the Santa Lucia waterfront area, one of Naples’s most charming neighborhoods. Then it’s back up to Via Caracciolo and the Villa Comunale, before heading back to your hotel for a short rest before dinner and perhaps a night out at one of Naples’s lively bars or clubs.

Logistics: This entire day is easily done on foot. Naples is one of the best walking cities in Italy.

Day 3: Pompeii/Sorrento

After breakfast, pick up your rental car, pack in your luggage, and drive from Naples to Pompeii, one of the true archaeological gems of Europe. If it’s summer, be prepared for an onslaught of sweltering heat as you make your way through the incredibly preserved ruins of a city that was devastated by the whims of Mt. Vesuvius nearly 2,000 years ago. You’ll see the houses of noblemen and merchants, brothels, political graffiti, and more. From Pompeii, get back in your car and it’s on to Sorrento, your first taste of the wonderful peninsula that marks the beginning of the fabled Amalfi Coast. Sorrento is touristy, but it may well be the Italian city of your imagination: cliff-hanging, cobblestone-paved, and graced with an infinite variety of fishing ports and coastal views. There, have a relaxing dinner of fish and white wine before calling it a day.

Logistics: Naples to Pompeii is all about the A3: a short 24 km (15 miles) brings you to this archaeological gem. From Pompeii it’s a short ride back on the A3 until the exit for Sorrento; from the exit, you’ll take the SS145 to reach Sorrento.

Day 4: Positano/Ravello

Your stay in Sorrento will be short, as there’s much of the Amalfi Coast still to see: Positano, your next stop, is a must. It’s one of the most-visited towns in Italy for good reason: its blue-green seas, stairs “as steep as ladders,” and white Moorish-style houses make for a truly memorable setting. Walk, gaze, and eat (lunch), before heading on to the less traveled, even-higher-up town of Ravello, your Amalfi Coast dream come true, an aerie that’s “closer to the sky than the sea.” Don’t miss the Duomo, Villa Rufolo, or Villa Cimbrone before settling in for a dinner in the sky.

Logistics: Sorrento to Positano is a 30-km (19-mile) jaunt, but the winding roads will draw it out for the better part of an hour—a scenic hour. From Positano, Ravello is another slow 18 km (11 miles) to the east, perched high above the rest of the world. Be prepared to use low gears if you’re driving a stick shift (as you almost surely will be).

Day 5: Matera

It’ll take a bit of a drive to get to Basilicata from the Amalfi Coast; leaving Campania and entering Basilicata is generally a lonely experience. Little-traveled roads, wild hills, and distant farms are the hallmarks of this province, which produces deep, dark aglianico wines and has perfected the art of peasant food. You’ll spend a while in your car to make it to Matera, a beautiful, ancient city full of Paleolithic Sassi (cavelike dwellings hewn out of rock)—but it’s worth it. Traversing the city is like taking a voyage through time. Spend the afternoon exploring the Sassi, but take care not to miss the new part of the city, too. Then enjoy a relaxing dinner at one of Matera’s excellent restaurants—just decide whether you want flavorful local beef (Le Botteghe) or a flurry of Basilicatan tapas (Lucanerie). Basilicata, you’ll soon discover, is full of unrivaled values at restaurants, and with such options you’ll be guaranteed to sleep well in the Sassi.

Logistics: It’s a long haul from your starting point, Ravello, to Matera. It’s a good thing Basilicata’s landscape is so pretty. Once in Matera, if you’re staying in the Sassi, get extra-detailed driving and parking instructions from your hotel beforehand—navigating through thousand-year-old alleyways can be challenging.

Day 6: Lecce

This drive will take a good 2½ hours, so get an early start. The Baroque city of Lecce will mark your introduction to Puglia, the heel of Italy’s boot. It’s one of Italy’s best-kept secrets, as you’ll soon find out upon checking out the spectacular church of Santa Croce, the ornate Duomo, and the harmonious Piazza Sant’Oronzo. The shopping is great, the food is great, and the evening passeggiata is great. Don’t miss the opportunity, if you wind up at a bar or café in the evening, to chat with Lecce’s friendly residents—unfazed by tourism, the welcoming Leccesi represent southern Italians at their best.

Logistics: It’s not far from Matera to Lecce as the crow flies, but the trip is more involved than you might think; patience is required. The best route is via Taranto—don’t make the mistake of going up through Bari.

Day 7: Bari

The trip from Lecce to Bari is a short one. Check into the pleasant Domina Hotel Bari Palace and spend the morning and afternoon wandering through Bari’s centro storico (historic center). The wide-open doors of the town’s humble houses and apartments, with bickering families and grandmothers drying their pasta in the afternoon sun, will give you a taste of the true flavor of Italy’s deep south. Don’t miss Bari’s castle and the walk around the ridge of the ancient city walls, with views of wide-open sea at every turn. Finish the day with a good fish dinner, and celebrate your last night in Italy by checking out one of the city’s multitude of lively bars—Bari boasts one of southern Italy’s most hopping bar scenes.

Logistics: This is one of your most straightforward, if not quickest, drives: just take the coastal S16 for 154 km (95 miles) until you hit Bari. It’s a two-lane highway, though, so don’t be surprised if the trip takes two hours or more. If you get tired, beautiful Ostuni (dubbed the “città bianca,” or the white city) is a perfect hilltop pit stop halfway there.

Day 8: Bari/Departure

Bad news: This is your wake-up-and-leave day. Bari’s Aeroporto Palese is small but quite serviceable. Exploit its absence of crowds and easy access and use it as your way out of Italy. Connections through Rome or Milan are more frequent than you might think. Plan on leaving with southern Italy firmly established in your heart as the best way to see the Italy that once was—and be thankful that you were able to see it while it’s still like this.

Logistics: Bari hotels offer easy airport transfers; take advantage of them. There are also regular public transport connections between the central train station and the airport. Return your rental car at the Bari airport; you won’t have to arrive at the airport more than an hour or so before your flight.

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