Shearwater Sailing leaves from Battery Park City and offers lots of different sailing options but we recommend the romantic Full Moon Sail (a 1 1/2 hour tour for $50/person). While you're out on the water, the sun sets and the city lights go up. The crew is cool and the price is right (they don't nickle and dime you for a plastic cup of champagne).
For another sailing option, check out FG's pick:
The Schooner Adirondack leaves from Chelsea Piers and sails from May to October. Take the sunset cruise (a 2 hour tour for $50/person) which includes drinks! When you return to land, grab dinner at one of these Chelsea tapas bars that we blogged about.
Bon voyage!
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