A Tall-Ship Sail on the Clipper City

Manhattan by Sail runs the Clipper City, a tall ship that sails the harbor from Pier 36 on South Street, below the Manhattan Bridge. When the canvas goes up and the engine goes quiet, the city sounds different: lines creaking, water on the hull, the skyline sliding past the rigging. It is the most theatrical way to see the Statue of Liberty from the water, and the crew will happily let you help haul a line.

Two sailings anchor the schedule as of October 2026: a Golden Hour Cocktail Sail of about an hour and a half, listed at $76 with a welcome drink, and a Sunset Jazz Sail of an hour and forty-five minutes with a live band, listed at $95. Book a date on the company's calendar; sunset sails fill first. Bring a layer, since it is always colder on the water than on the pier. The operator posted that a July squall damaged some rigging and that full repairs are planned for the winter, so ask how many sails are flying when you book.