Photographer Billy Black spent the early days of his career on the island of Manhattan. It was several years, however, before he took to the waters off Manhattan.

“I started my photographic career living and working in Manhattan, and though my father and I bought an Ericson 39, we sailed it mostly on Long Island Sound. After my studio was robbed in 1981, I gave up on living in New York, and my boat and I eventually pushed on to Rhode Island. My first opportunity to sail in Manhattan came in 1987. A friend of mine, Michael Fortenbaugh, launched the Manhattan Yacht Club [now the Manhattan Sailing Club] to bring sailing to an urban population who either couldn’t afford boats or didn’t want the trouble of owning them. Michael was always looking for support boats for regattas, and one time I brought my boat down from Rhode Island to act as a committee boat for one of Michael’s regattas. After the regatta, heading home, I found myself sailing up the East River without an engine. I’ll never forget being under full sail on a starboard tack with a big Genoa. I was attempting to sail through Hell Gate, under the Throgs Neck Bridge, and I went nowhere for an hour. More than once I thought the boat would go sideways and we’d eat it, but the tide finally turned and we made it home.”

The exact area that’s defined by New York Harbor is the object of some debate. Some see it as the region below and around the southern tip of Manhattan. Others include these waters and extend the boundaries down to Gravesend Bay, southwest of Brooklyn. Still others use the term more generously to take in the sundry waterways that touch the five boroughs, including the lower stretches of the Hudson River, the East River, the Harlem River, Jamaica Bay, Raritan Bay, and the southwesternmost sections of the Long Island Sound. New York–based angling writer Peter Kaminsky has estimated that there are more than 1,260 miles of coastline around greater New York—crags, crooks, and crannies included. Not all of these waters are inviting for sailors, but many are; Sail America claims that if you were to draw a 50-mile circle around Battery Park, you’d encircle a region with the highest number of registered sailboat owners in the country.

There are many sailboat clubs scattered around the five boroughs, with a nice concentration of clubs near South Street Seaport and Chelsea Piers. To find the mother of all yacht clubs, however, you must move a few blocks away from the harbor proper to the headquarters of New York Yacht Club, one of Manhattan’s great contributions to the world of yachting. The club was started one June afternoon in 1844 on the deck of John Cox Stevens’ new yacht Gimcrack, which was anchored off Battery Park. After forming the club for the purpose of “weekend New York Harbor racing, and summer cruises in the cooler New England waters,” Stevens and his eight accomplices made plans to gather three days later and cruise to Newport, Rhode Island. They did so, and the waters around Newport have been a significant sailing ground for club members ever since. Suffice it to say, the NYYC has been responsible for instituting a few races in its time, including the Annual Regatta, the Atlantic Challenge Cup, and a little event called the America’s Cup. Should you find yourself in midtown Manhattan, scan your little black book (or Black-Berry) for someone who knows someone who is among the club’s three thousand members. The NYYC’s beautiful Beaux Arts clubhouse is home to the world’s largest collection of full- and half-hull models.

The boating community in New York—like everyone else—was tremendously shaken by the events of 9/11. “Richie Wilson was in New York Harbor on the Great American II during that second week of September in 2001,” Billy recalled. “He was ready to start a record attempt from New York to Australia. When the towers came down, he found himself on the fringe of Ground Zero and postponed his departure to pitch in. A week later he rescheduled his departure and called me to come take the pictures. All the boat ramps in lower Manhattan that I’d been using for twenty years were closed. The National Guard, the Coast Guard, and the Navy were everywhere. We finally found an open ramp and launched the boat. We’d made it a hundred yards before we were pulled over and turned around by a Coast Guard boat from my home waters off Newport. Richie left without help from us and broke the record from New York to Australia.

“I was back in New York Harbor in the spring of 2006 to photograph the Orange II, which was preparing to break the transatlantic record. It was great to see the waterfront in the middle of a big revival. Marinas were being built on the New Jersey side of the Hudson; old piers were being renovated on the Manhattan side. The New York waterfront seems to be undergoing a great resurgence.

“If I had a few hours to take someone for a sail around New York, I think I’d take them from the George Washington Bridge down to the Statue of Liberty,” Billy said. “It’s such an incredible transition. The Upper West Side is so very green; if you blocked out the buildings, you’d think you were in upstate New York. Traveling south, the Manhattan shoreline gets more and more urban. By the time you reach the Battery, everything is glass. On my most recent trip, we pulled the Orange II past the driving range at the Chelsea Piers; it was a tremendous New York moment, as not a single person stopped hitting balls to marvel at this extraordinary boat! We continued down to the Battery, and we were taking some shots with the western light—except it was being simultaneously backlit by the reflected light. It was one-of-a-kind lighting for a unique craft.”

Billy Black has many memories of New York Harbor, of friends who left for adventures never to return from sea, and of the devastation that followed the 9/11 attacks. One memory that’s especially poignant involves a brief sail with his wife’s mother, Beverly. “My wife, Joyce, is originally from Denver, and a few years back Beverly came out to spend a little time on the East Coast,” Billy recalled. “The morning after she arrived, we took our boat from the Palisades on the New Jersey coast for a sail to the city. That first view from the river of the beautiful green shoreline gave Bev an indelible and atypical impression of the city. We sailed through the waters past the old Cunard Line docks, under the bridges, and past the piers. The ultimate view on that beautiful morning was the Statue of Liberty. It felt as if we could reach up and touch it. To view a familiar landmark from a small boat on the water is an unforgettable thrill. Seeing the statue so close to Ellis Island, you can’t help but feel an emotional connection with the people who came as immigrants to this huge, strange land and saw this glorious statue as we were seeing it.

“Though she always enjoys the energy, activity, pulse, and taxi horns of the city, Bev never forgets the beauty of her first view of New York from the harbor. It was a tremendous thrill for me, too.”

Billy Black is based in Portsmouth, Rhode Island. He’s known among his clients for his intrepid seamanship and for going the extra mile—even under the most challenging conditions—to get that important shot, and for displaying the patience and sensitivity to capture the spirit of an exotic location and its people. Billy has traveled all over the world to photograph places and the people who live and work there. He has worked for all the major boating publications, many builders, and suppliers of gear and services who help people get on the water. Billy’s stock includes over half a million images, some of which are displayed at www.BillyBlack.com.

Getting There: New York City is served by most airlines.

Best Time to Visit: The months of May through October present the best sailing opportunities on New York Harbor.

Charter Operators: Many companies offer day sails in Manhattan; fewer offer bareboat options. The Atlantic Yachting Association (917-291-7254; www.atlanticyachting.org) offers limited bareboat charters. The number of available yachts increases as you move toward New Jersey and Long Island Sound. The Manhattan Sailing Club (212-786-3323; www.myc.org) hosts races on weeknights and Saturdays, and may have crewing opportunities for visitors.

Moorings: New York Harbor offers a great variety of berthing options, especially as you move away from Manhattan island. On Manhattan, some space for transient sailors is available at the West 79th Street Boat Basin 212-496-2105; www.nycgovparks.org).

On-Shore Accommodations: The New York State Department of Tourism (800-CALL-NYS; www.iloveny.com) has a comprehensive listing of accommodations in the Big Apple.

Bay of Islands, north of Auckland, offers many secluded spots where cruisers can hide away.