Classic Harbor Line Sunset Sail

There are many ways to see the harbor; very few of them involve actual sails. Classic Harbor Line runs graceful schooners and 1920s-style motor yachts out of Chelsea Piers, and the evening sail is the one worth planning a night around — engines mostly quiet, canvas up, a drink in hand as the boat slips down the Hudson toward the Statue of Liberty while the sun drops behind New Jersey.

This is the unhurried, grown-up version of a harbor cruise: small passenger counts, teak decks, blankets when the air cools. Sailings, boats, and routes change with the season, so check the operator's site for the current schedule and book ahead — sunset departures sell out first, especially on weekends.