The 15 Best Sailing Trips in New York

1.Manhattan Architecture Yacht Cruise

★★★★★★★★★★5.0 · 1,395 reviews · 2 hours 45 minutes (approx.) · from $113Our pick

From Chelsea Piers, circle Manhattan aboard a 1920s-style yacht with live commentary from a New York chapter AIA member. Look for the Chrysler Building, Statue of Liberty and 18 bridges from the cabin or open bow. The 2-hour-45-minute cruise includes one beer, wine or soft drink; guides vary by departure.

“Relaxing harbor tour around Manhattan... with an excellent guide who highlighted all major architectural callous along the way. Boat was very nice with bar service & snacks (as well as clean restrooms... as tour is 2 hrs 45 minutes).”

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2.Holiday Yacht Cruise with Jazz, Cocoa & Carols

★★★★★★★★★★4.7 · 568 reviews · 1h 30m · from $134

Board the classic Yacht Manhattan or Manhattan II at Chelsea Piers for a 90-minute holiday cruise. You’ll pass Lower Manhattan, Governors Island, the Statue of Liberty and Ellis Island from a heated salon, with live jazz, carols, cocoa, cookies and one complimentary drink. Assigned seating keeps the ride comfortable, while the full bar offers extra drinks for purchase.

“This was FABULOUS. I thought there was a 50/50 shot it would be a cheesy waste of time. But it turned out to be one of our favorite experiences in NYC. The staff were all SO kind, always offering photos/refreshments, and the jazz band was great!! My only warning is the hot chocolate is very clove-y, which we would have passed on if we knew. But this was a 10/10 and our photos are amazing to remember the trip!”

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3.Statue and Skyline Cruise Aboard a Luxury Yacht

★★★★★★★★★★4.8 · 540 reviews · 1h 30m · from $60Best value

Board a 1920s-style yacht at Chelsea Piers for a 90-minute cruise on the Hudson River and New York Harbor. Expect assigned tables, one included drink, a climate-controlled observatory, open decks, and captain’s commentary as you pass the Statue of Liberty, Ellis Island, and Manhattan landmarks. Crew names vary by sailing.

“Amazing value for money, the guides were very knowledgeable. The boat its self was lovely, the drinks available on board were amazing too.”

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4.Sunset Yacht Cruise

★★★★★★★★★★4.9 · 461 reviews · 90 minutes - 3 hours · from $113

Sail the Hudson River at sunset with Classic Harbor Line, passing Lower Manhattan, Battery Park, Ellis Island, and the Statue of Liberty. You get an assigned table in the grand salon, access to open decks and a glassed-in observatory, and one included drink. The cruise lasts 90 minutes to three hours, depending on the option and season, so check the exact departure and duration before booking.

“Excellent Cruise very organized and well planned. Nice drinks on board. Staff was very polite.”

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5.New York City Sunset Cruise on a Yacht

★★★★★★★★★★5.0 · 331 reviews · 1 hour 30 minutes (approx.) · from $113

Board Classic Harbor Line at Pier 62 for a 90-minute cruise around Manhattan. You’ll pass the Statue of Liberty and Ellis Island, with skyline views from indoor seating or the open deck. One beverage is included, tables are assigned, and relaxing music plays, but the cruise is not officially narrated.

“Worth money! Intimate and curated! The live jazz was amazing and sailing under the city lights! Saw the Brooklyn bridge and Statue of Liberty! Perfect way to end our anniversary weekend”

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6.Evening Jazz Cruise on the Yacht Manhattan

★★★★★★★★★★4.8 · 285 reviews · 1h 30m · from $134

Board the Yacht Manhattan at Chelsea Piers for a 90-minute evening harbor cruise with live jazz and one included alcoholic drink. Settle at your assigned table in the climate-controlled salon or head to the open decks for views of the Financial District, Governor’s Island, the Statue of Liberty, and Ellis Island. Food is available to buy, but this is a light onboard menu, not dinner.

“Great New York experience for visitor or ardent locals. The Boat Band is superb and the views breathtaking.”

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7.City Lights Yacht Cruise with Drink Included

★★★★★★★★★★4.8 · 241 reviews · 75 - 90 minutes · from $78

Cruise the Hudson at night aboard a 1920s-inspired yacht, with a reserved seat in the climate-controlled grand salon and access to open decks. Take in Lower Manhattan, Battery Park, Governor’s Island, the Statue of Liberty and Ellis Island. One drink is included; extra drinks and gratuity are not.

“Beautiful boat and lovely crew. We loved it so much.”

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8.2.5-hour Guided Sailboat Tour

★★★★★★★★★★5.0 · 181 reviews · 2 hours to 2 hours 30 minutes (approx.) · from $118

Join a small-group sail from Brooklyn’s Pier 5 for a 2 to 2.5-hour circuit of New York Harbor. With no more than six people aboard, you’ll pass the Statue of Liberty, Ellis Island, and Governors Island, motor under the Brooklyn Bridge, and sail toward One World Trade Center. Captains named Ian and Andrew have led trips, though your captain may vary.

“Best value in Brooklyn! Ian was an amazing host for this 2+ hour sail with 6 maximum passengers. Honestly you don’t know what you are missing if you pass on this one.”

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9.New York City Sailboat Day Cruise to the Statue of Liberty

★★★★★★★★★★5.0 · 152 reviews · 1 hour 45 minutes (approx.) · from $60

Leave Chelsea Piers on the two-masted Adirondack for a 1-hour-45-minute to 2-hour sail past the Financial District, Ellis Island, and the Statue of Liberty. One drink is included, and the trip returns to Pier 62. Expect open-air harbor views rather than a full guided tour.

“This is a unique opportunity to sail on the river - the views are stunning-crew very nice. Simply wonderful”

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10.Statue of Liberty Cruise aboard a Classic Sailboat

★★★★★★★★★★5.0 · 129 reviews · 1h 45m · from $60

Set sail from Chelsea Piers on a 105-foot schooner for a 105-minute trip down the Hudson, past Ellis Island and the Statue of Liberty. The crew raises sail when conditions allow, and the route may extend toward Governors Island and Buttermilk Channel. One drink is included; the exact boat may vary.

“Best value tour in NYC. A truly amazing experience to be under sail on the Hudson in the America II. if there's a better way to view the skyline and the statUe of liberty... I haven't found it yet. INCREDIBLE VALUE.”

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11.Sunset Cruise on a Small Yacht with a Drink

★★★★★★★★★★4.8 · 85 reviews · 1h 30m · from $85

Set sail from Pier 62 at Chelsea Piers on a 90-minute sunset cruise aboard a small yacht. Take in Lower Manhattan, the Statue of Liberty, and other harbor sights from the open bow or the glassed-in cabin. Your ticket includes one drink and light tapas. Captains and crew vary, with past sailings led by Captain Felix, Captain Sanjay, and Captain Tim.

“The staff running the cruise were really outstanding! The food and drinks were good, the boat was clean and comfortable, and the trip was a great deal of fun. I would do it again with a larger group of friends some time.”

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12.Brooklyn Sightseeing Sailboat Cruise

★★★★★★★★★★4.9 · 49 reviews · 2h 30m · from $125

Board a Brooklyn sailboat for a 150-minute trip past Governors Island, the Statue of Liberty, Ellis Island, and the Brooklyn Bridge, with Manhattan’s skyline as a constant backdrop. A captain leads the trip; Ian and Andrew have both guided sailings. Bring your own food and drinks, and expect an intimate group of no more than six.

“Ian is a excellent Captain. Prompt in meeting everyone. Very knowledgeable in NY history @ sights. Well worth the money. Being on the water on a beautiful day in NY “priceless””

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13.Hudson River Fall Foliage Yacht Tour

★★★★★★★★★★4.4 · 47 reviews · 2h 30m · from $110

For 150 minutes, Yacht Kingston takes you north from Chelsea Piers along the Hudson River, with views of the Upper West Side, the Palisades and the George Washington Bridge. You get wrap-around seating, open windows and access to the forward deck, plus one drink. The English-speaking captain leads the cruise, though narration can be hard to hear.

“Our guide and boat captain was knowledgeable and personable. He and the first mate helped make trip very enjoyable. Our party of 7 all felt it was a good choice.”

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14.Grand Palisades Fall Foliage Yacht Tour

★★★★★★★★★★4.9 · 46 reviews · 2 hours - 135 minutes · from $110

Board the 1920s-style yacht Manhattan at Chelsea Piers for a northbound Hudson River cruise of about two hours, with time to admire Upper Manhattan, the George Washington Bridge, and the Palisades. An English-speaking Urban Naturalist explains the area’s geology and ecology. You get assigned indoor seating, outdoor deck access, and one included drink.

“The tour was nice and offered multiple choices for photographs on both sides of the river. The food was excellent and there was something for everyone! The staff was very polite and helpful. I am glad this was not a narrated tour, the main interest was to see the sights, and take photographs. We recommend this to everyone. We would do it again, except, we would do it one or two weeks later so we could catch the real colors of the fall.”

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15.Holiday Jazz Classic Motor Yacht Cruise

★★★★★★★★★★4.5 · 35 reviews · 1h 30m · from $134

Spend 90 minutes on the Hudson aboard the classic yacht Manhattan or Manhattan II. You’ll sit in a heated, holiday-decorated salon, hear a live jazz trio play seasonal tunes, enjoy homemade cookies and one included drink, and pass landmarks including the Statue of Liberty. There’s no narrated tour, so come for the music, atmosphere, and nighttime views.

“Amazing experience. The jazz music what great and the staff were lovely. Amazing views of the Statue of Liberty”

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