2026 Tickets Now Available | May–October | Pier 16 | $5–$70
Experience New York City like never before on a sail aboard the historic 1885 schooner Pioneer with the South Street Seaport Museum! From May through October, this exclusive opportunity offers you the chance to take in the breathtaking views of the Big Apple from the deck of a National Register-listed vessel.
As you set sail on this unforgettable journey, you’ll see some of the city’s most iconic landmarks, including the Brooklyn Bridge, Statue of Liberty, Lower Manhattan’s architectural treasures, Governors Island, Ellis Island, and more. Whether you’re a seasoned New Yorker or a first-time visitor, this adventure promises to be a truly unforgettable experience.
But that’s not all––as a guest on board, you’ll have the chance to get hands-on and help our knowledgeable crew raise a sail or simply sit back and relax as you soak up the stunning scenery. And, for the perfect al fresco dining experience, bring along your favorite meal or snack, along with your preferred beverages—even a bottle of wine—to sip on deck.
Check out the variety of 2026 Pioneer sailing opportunities below, we can’t wait to welcome you aboard!
Give the gift of adventure aboard this one-of-a-kind schooner this holiday season! Perfect for history buffs, maritime and sailing enthusiasts, romantics, or anyone who loves the water, a sail on the 1885 schooner Pioneer is an unforgettable way to experience New York City. The Pioneer sailing season runs from May through October, but you can reserve tickets or book a private charter now to give the promise of adventure all year long!
2026 Offerings to Sail on Pioneer:
Know Before You Go
Tour routes are subject to change due to unpredictable boat traffic in the Harbor and weather, though captains will do their best to include the sites listed. Read the full On the Water with the Seaport Museum FAQ for more details on the sailing experience.
About the Schooner Pioneer
Pioneer was built in Pennsylvania in 1885 to carry sand and heavy cargoes along the Delaware River. Unlike almost all American cargo sloops and schooners that were made of wood, Pioneer was constructed with a wrought iron hull because she was built in what was then the nation’s center for iron shipbuilding. Today, she is the sole American merchant sailing vessel with an iron hull. Through offering sails aboard Pioneer, the Seaport Museum provides an exceptional experience to the public, catering to inquisitive students, seasoned New Yorkers, and eager visitors alike. By offering unique opportunity to venture out onto the water, this remarkable vessel grants guests a new vantage point to see the city allowing guests to forge a deeper connection with New York’s maritime past and present, illustrating exactly “Where New York Begins.”
Charter This Historic Vessel
Looking for a unique and unforgettable way to celebrate a special occasion with friends and family or impress your clients with an exciting corporate outing? Look no further than the Seaport Museum’s private charters on the historic 1885 schooner Pioneer and the 1930 tugboat W.O. Decker.
Get a Taste of Sailing on Pioneer
Education Programs on Pioneer
Sail New York Harbor aboard the historic 1885 schooner Pioneer. Students help raise sails, see the Statue of Liberty and other Harbor landmarks, observe a variety of ships and waterborne commerce, and engage in exciting hands-on activities.