Manhattan by Sail: The Best Getaway in New York City

Manhattan by Sail

Tshh-tsh-tsh-tsh-tsh-tsh-tsh, says the cymbal to the electric guitar and keyboard. Like the boat we’re on, couples are bobbing to the beat of the Harbor Cats jazz band as the Manhattan by Sail schooner cruises ever so gently alongside the bright lights of the big city. It’s late on a weeknight in New York and this 158-foot-long vessel feels like the best place in the world to be.

Experiencing a place from the water that flows around and through it has always proven to be a good idea. So wherever I go, there I am. I’ve hummed La Vie En Rose down the Seine on the Bateaux-Mouches. I’ve danced on a riverboat up The Thames in London and rowed on The Thames in New London. I’ve taken a canal tour of Copenhagen and a gondola ride of Venice. I’ve Water Taxi’d Chicago, tacked around Alcatraz, paddled on a sailing canoe in Maui and kayaked the Hudson River. But none of those aquatic adventures quite compares to this one.

manhattan by sail toursIt’s the easiest, most relaxing of romantic escapes a New Yorker or tourist can have. You board at Pier 17 in South Street Seaport—after devouring dinner at Red Hook Lobster Pound or Asia Dog during Smorgasburg—you grab a drink at the bar, you find a seat or lean against the railing and let the trumpet and tide take you out.

After a sunny day, you find yourself with fifty other passengers applauding the music and a cool refreshing breeze. The Shearwater and The Clipper City, that’s the boat we’re on—inspired by grand old lumber-hauling schooners of the early 1900s—are the realized dream of Tom Berton, a real estate workaholic-turned-captain of his own company.

Tom has created many other fantastic floating tours, like the Lobster and Beer Lovers Sail and Craft Beer Tasting day and sunset sails. While each charter is unique, there is something about Manhattan by night, those thousands of twinkling stars in the skyline, the soundtrack of New York reverberating off the steel hull, that makes the Jazz Sail especially enchanting.

By the time we voyaged up Buttermilk Channel, glided passed Governors Island to the Statue of Liberty and back to Pier 17, it felt like we were gone much longer than a few hours. We never lost sight of the city, and yet this sail offered a more stress-relieving getaway than a trip to Long Island. No traffic or train delays, no schlepping bags. And after you’ve docked, the sounds of the harbor and the Harbor Cats linger on a lot longer than any other river ride I’ve ever known.

Visit to book a ticket for the Clipper City or Shearwater. Jazz Sail is every Wednesday, 9:45-11:45pm, $95/person.