Sail250 Harbor Sail aboard Schooner Adirondack — Fleet Week Sails from Chelsea Piers

Stand on the Adirondack’s teak rail and the city rearranges itself: lower Manhattan drawn long and elegant across the water, the Statue of Liberty framed like a punctuation mark, and the Brooklyn Bridge arching to Brooklyn. Schooner Adirondack — an 80-foot wooden pilot schooner operated by Classic Harbor Line — sails from Chelsea Piers (Pier 62) into the Hudson and New York Harbor for a 1.75 to 2-hour cruise designed to put you up close to visiting Tall Ships and Fleet Week naval vessels during Sail250. This is sightseeing without glass: we shut the engines and set sail, spreading roughly 2,000 square feet of canvas so you feel the harbor breeze and hear the rigging sing. The route threads past Ellis Island, offers unobstructed skyline views, and positions you alongside historic ships gathered for the festival. The Adirondack’s design by Scarano Boat Building and its racing pedigree — record finishes in the Chesapeake Bay Schooner Race — make it lively yet comfortable for up to 49 guests. Coast Guard–certified captains and crew combine hospitality with seamanship; they welcome questions about the vessel and the waterfront as they trim sails and steer through shipping channels. What makes this experience special to New York’s outdoor scene is the perspective: landmarks are read from water level, where geology meets human history — the Manhattan shoreline, the ironwork of bridges, the sandy approach to Liberty Island — and the harbor’s working life remains visible in tugboats and navy escorts. For Fleet Week and Sail250 the harbor becomes a stage, and Adirondack gives you front-row seats without the crush of shore crowds. Practical details: meet at Chelsea Piers (Pier 62) on the Hudson at 22nd Street; check-in info is provided after purchase. Tickets start at $52–$58 for adults, with child and infant pricing available; a complimentary beverage is included. Food is not included; light snacks are allowed. If you have a group of 17 or more, call 212-627-1825 for group bookings and gratuity policy. The operator emphasizes accessibility with some limitations; contact the office to plan accommodations. Conservation-wise, Classic Harbor Line partners with Cup Zero to reduce single-use plastics, a small but meaningful step for marine stewardship in a high-traffic harbor. Whether you want a relaxed two-hour sail, a study of harbor operations, or a close encounter with tall masts and naval power, the Schooner Adirondack delivers a concise, memorable maritime view of New York City that’s as instructive as it is cinematic. Bring layered clothing for harbor wind, a phone with a wide-angle lens, a bag for essentials; listen to crew stories about the schooner, ask about rigging, and truly savor how a short two-hour sail sharpens your sense of New York’s maritime life and scale.