Pioneer is a National Register-listed schooner built in 1885, and a sunset sail puts you on her deck as the sails fill and the light drops behind the Statue of Liberty. The museum encourages guests to bring a bottle of wine and a picnic, which makes it feel more like a private outing than a tourist cruise. If you want a boat night on the harbor with real history under your feet, book this sunset sail.
What to expect
Check in at Pier 16, board, and head out under sail into the harbor for about two hours. The route varies with boat traffic and weather, but Lady Liberty and the downtown skyline are the usual highlights. Golden hour on deck, with the sails up and the skyline behind, is the moment everyone photographs.
Good to know
- Take the 2, 3, 4, 5, A, C, J or Z train to Fulton St and walk to Pier 16.
- Bring your own wine and snacks to enjoy on deck.
- Arrive during the check-in window; boarding closes shortly before departure.
- Bring a layer; it gets cool on the water after sunset.
- Routes can change with weather and harbor traffic.
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Common questions
Can I bring alcohol on the Pioneer sunset sail?
Yes. The museum invites guests to bring a bottle of wine and a meal or snack to enjoy on deck.
How long is the sunset sail?
About two hours.
Where does it depart?
Pier 16 at the South Street Seaport.
