Sailing Charter Near Me: Tribeca Sailing's 1964 Hinckley Tara at Pier 25

Tara was built in 1964 in Southwest Harbor, Maine, as one of only five custom Pilot 35 sailboats Henry R. Hinckley and Company ever made, and she now takes private groups of up to six around New York Harbor from Pier 25 in Tribeca. Tribeca Sailing prices its two-hour City Sunset Sail at $850 for one to three people and $975 for four to six, on dates like Friday, October 30 from 5:00 to 7:00 pm. If you want a sailing charter near me that feels like a friend's classic yacht rather than a tour boat, this is it.

The Pilot design started with Sparkman and Stephens in 1945, and Hinckley bought it in 1955 before stretching it to 35 feet 9 inches and switching to fiberglass around 1962. Of 117 fiberglass Pilots, only five were the custom version, with a raised doghouse cabin top and a galley running the length of the starboard side. Tara is the 25th fiberglass Pilot 35 off the line, finished with Philippine mahogany below decks.

Her first owner sailed her for 15 years and named her after the plantation in Gone with the Wind. A second owner kept her for 30 years, and the current owner bought her in 2013, the year Tribeca Sailing began. The company says more than 7,000 passengers have crossed her deck since then. Her refit history is part of the story: a new diesel engine in 2012 and a new teak toe rail from Jagger's Boatworks in 2018.

One detail is worth asking the captain about once you clear the pier. When Tara's mast was pulled for replacement in December 2014, the owner found a 1921 silver dollar placed at its base for luck, an old sailor's custom, and he put it back when the mast was stepped again in the spring of 2015. It is still there, under the spar you will be leaning against.

That sense of an owned, loved boat runs through the trip. Recent Google reviews posted on the company site name Captain David, describe him handing out blankets on a chilly sunset sail, and credit him with helping one guest plan a surprise proposal. Expect conversation and harbor history rather than a scripted commentary, since the cockpit holds your group and the captain and no one else.

Tribeca Sailing runs separate trips from New York and from Liberty Landing Marina in Jersey City, and the booking page lists them as different items. For a Manhattan start, choose the options marked NY Departure, which leave from the south side dock of Pier 25 at North Moore Street. Picking the wrong item would put you at a dock in New Jersey, across the river from your dinner plans, so check the bullet in the trip name before you pay.

The City Sunset Sail is the company's most popular charter, at $850 for groups of one to three or $975 for four to six. The 90-minute City Lights Sail leaves at 8:00 pm, after dark, when the Statue of Liberty's torch and the Freedom Tower are lit. In the 2026 calendar the New York sunset and night sails run through October 31, and the two-hour daytime sail continues until November 15.

Read the policy before paying, because it is firmer than most. Charters go out in light rain, cloud, cold and small craft advisories, and the company will not reschedule on the strength of a forecast. The captain decides on thunderstorms, lightning or dangerous wind and tries to call about two hours before the start. If the company cancels, you get one rescheduled sail or a full credit that never expires, but no cash refund.

All bookings are final unless you add 48-Hour Cancellation Protection for 20 percent of the charter fee, which lets you cancel up to 48 hours out and recover the fee minus that 20 percent. One reschedule is allowed with 48 hours' notice and a $300 fee. Guests not at the dock at departure time lose the booking, so build in time for subway delays on a Friday evening.

The pricing page invites guests to bring their own food and drinks. With six people in a 35-foot cockpit, the winning formula is compact: a small cooler, a cheese and charcuterie board, plastic cups instead of glass and a bottle of something sparkling for the sunset. Pack soft-soled shoes so you do not scuff the varnished wood, and a layer heavier than you think, since October breezes on the Hudson cut through a light jacket.

Brookfield Place, at 230 Vesey Street, is the most convenient stop on the way for provisions, with the Hudson Eats food hall about a fifteen-minute walk south along the river path, a sensible place to buy sandwiches and drinks before you board. The same route passes North Cove Marina, where many of the harbor's private yachts tie up, which makes a good sanity check on the walk to Pier 25.

The company's directions list the 1 to World Trade Center-Cortlandt, the E to World Trade Center, the R to Cortlandt Street, the 4, 5 and 6 to Fulton Street and the A, C, 2 and 3 to Chambers Street. Chambers Street is the closest of those, a walk of about ten minutes west to the Hudson River Park path. Phone calls and texts go to (201) 938-9359.

After a City Lights sail, Tribeca's restaurants are a few blocks inland along North Moore and Hudson Streets. Skip driving: street parking near Pier 25 is scarce at dinnertime, and a cab or the subway from Chambers Street will get you home faster than circling the West Side Highway.

Book NY Departure, buy the cancellation protection if your date is not firm, and arrive early enough to be at the dock before the start time. If Tara is taken, Narwhal Yacht Charters and Go Sailing NYC run six-guest charters from Chelsea Piers, and Classic Harbor Line sells individual schooner tickets from Pier 62 through November 1.