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Tall ships played a big role in the history of Manhattan Island. You now have a chance to board one of them and take a 90-minute tour of the picturesque and fascinating New York Harbor. Manhattan by Sail offers all kinds of tours, including basic sails around the island to cocktail parties, wine tasting, sunset tours, weddings, and private charters on one of their two magnificent sailboats.

Shearwater, built from native hardwoods in 1929, is the 82-foot schooner, an elegant Gatsby-era yacht that can accommodates up to 48 passengers. Clipper City is a replica of schooners that used to haul lumber a century ago, a 158-ft. long sailing ship that is New York’s biggest and most elegant and can accommodate 134 passengers.

Rating: ⭐⭐⭐⭐⭐

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