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.
It’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 manhattanbysail.com to book a ticket for the Clipper City or Shearwater. Jazz Sail is every Wednesday, 9:45-11:45pm, $95/person.
The co-founder and editor-at-large at offMetro, Lauren is a sustainable travel specialist and freelance journalist with frequent bylines in National Geographic, Bicycling Magazine and Shape. Follow Lauren’s adventures at @laurenmati.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram