Sailing the 1885 Schooner Pioneer

The South Street Seaport Museum keeps a working piece of the old port afloat: Pioneer, a schooner built in 1885, which still takes the public out under sail from Pier 16. Passengers can help raise the sails, the crew talks about the ship and the harbor she worked, and the whole trip feels less like a cruise than a lesson in how New York used to move its goods. The museum invites you to bring your own food and drinks aboard, a bottle of wine included.

The 2026 season has ended; the museum says it will be back on the water in 2027 and announces new dates through its mailing list. Fares run $5 to $70 depending on the sail as of October 2026, which puts it among the best-value boat rides in the city. Sign up for the list in late winter, book an evening sail when the schedule opens, and pack a picnic. Pair it with the museum's galleries on Water Street or a walk up the Seaport's cobbled blocks.