15 Best New York City Sailing Trips Worldwide

Cruises & Boat Tours, Luxury Yacht Trips, New York City, New York City Sailing Trips, Sailing, Tour Reviews

Manhattan Architecture Yacht Cruise

/ June 12, 2026

1.Manhattan Architecture Yacht Cruise

A 1920s-style yacht circles Manhattan for 2h45, with AIA architect narration, bridge views, and one free drink—plus great photo angles.

NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

/ July 24, 2026

2.NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

Cozy 90-minute NYC yacht cruise with jazz, carols, and cocoa. See the Statue of Liberty and Ellis Island from heated comfort.

★ 4.7

“Fantastic live jazz band on board doing all the Christmas classics. Thoroughly enjoyed! Beautiful to see skyline and Statue of Liberty all lit up! Yummy cocktails and cookies too. Highly recommend.”

568 reviews1.5 hoursFrom $134by Classic Harbor Line - New York City

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Cruises & Boat Tours, Luxury Yacht Trips, New York City, New York City Sailing Trips, Sailing, Tour Reviews, VIP

Manhattan: Statue and Skyline Cruise Aboard a Luxury Yacht

/ July 25, 2026

3.Manhattan: Statue and Skyline Cruise Aboard a Luxury Yacht

90-minute Manhattan Statue of Liberty and skyline cruise from Chelsea Piers on a luxury yacht, with 1 drink and indoor comfort.

★ 4.8

“Perfect trip with perfect hosts - the boat was beautiful, not crowded and the whole time was just lovely”

540 reviews1.5 hoursFrom $60by Classic Harbor Line - New York City

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City Tours, Cruises & Boat Tours, Evening Experiences, Luxury Yacht Trips, New York City, New York City Sailing Trips, Sailing, Sunset Sails, Tour Reviews

New York City: Sunset Yacht Cruise

/ July 29, 2026

4.New York City: Sunset Yacht Cruise

Sunset yacht cruise on the Hudson with a complimentary drink, assigned table seating, and sweeping views of Lower Manhattan and the Statue of Liberty.

★ 4.9

“Cozy and intimate but safe and pleasant. Staff was great. Views were beautiful despite quite a bit of fog. Much preferred to a larger vessel.”

461 reviews3 hoursFrom $113by Classic Harbor Line - New York City

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New York City: Sunset Sail Aboard a Schooner

/ August 6, 2026

5.New York City: Sunset Sail Aboard a Schooner

Sail the Schooner America for a 2-hour NYC sunset near the Statue of Liberty and skyline, with one included drink and crew service.

★ 4.9

“the sunset sail was amazing. we enjoyed every moment of it and the staff was very helpful and kind. i would highly recommend it to anyone who is planning a trip to nyc.”

344 reviews2 hoursFrom $101by Classic Harbor Line - New York City

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City Tours, Cruises & Boat Tours, Evening Experiences, Luxury Yacht Trips, New York City, New York City Sailing Trips, Sailing, Sunset Sails, Tour Reviews

New York City Sunset Cruise on a Yacht

/ August 7, 2026

6.New York City Sunset Cruise on a Yacht

A 90-minute NYC sunset yacht cruise from Chelsea Piers with skyline views, Statue of Liberty close passes, and a complimentary drink.

★ 5.0

“SO GREAT!!! Impeccable vibes. The jazz band, the lighting, the dazzling sunset city views, the breeze off the water…we didn’t want to get off the boat! 100/10 recommend!”

331 reviews1 hour 30 minutes (approx.)From $113.23by Classic Harbor Line NYC

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Cruises & Boat Tours, Evening Experiences, Luxury Yacht Trips, New York City, New York City Sailing Trips, Sailing, Tour Reviews

NYC: Evening Jazz Cruise on the Yacht Manhattan

/ August 11, 2026

7.NYC: Evening Jazz Cruise on the Yacht Manhattan

90-minute NYC evening jazz cruise on the Yacht Manhattan from Chelsea Piers with live jazz, Statue of Liberty views, and 1 drink.

★ 4.8

“We really enjoyed the views of The NYC skyline and Jersey skyline at night were so beautiful - especially with the great jazz ensemble playing along the way. The staff on the boat were so friendly and kind.”

285 reviews1.5 hoursFrom $134by Classic Harbor Line - New York City

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Cruises & Boat Tours, Evening Experiences, New York City, New York City Sailing Trips, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews

NYC: Sunset Sail Aboard Schooner Adirondack

/ August 12, 2026

8.NYC: Sunset Sail Aboard Schooner Adirondack

Sail into NYC’s sunset on the 80-foot Adirondack from Chelsea Piers. See Battery Park, Ellis Island, and the Statue of Liberty.

★ 4.9

“One of the best activities New York has to offer, whether you're a local (we've lived in the city for 30 years) or a visitor. The experience of seeing downtown New York, Ellis Island, and the Statue of Liberty from the water is magical. On top of that, the whole operation is flawless-- the ticketing…”

283 reviews2 hoursFrom $90by Classic Harbor Line - New York City

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NYC Statue of Liberty Tall Ship Sail aboard Clipper City

/ August 13, 2026

9.NYC Statue of Liberty Tall Ship Sail aboard Clipper City

Tall ship cruise aboard Clipper City from Pier 17: Statue of Liberty and Ellis Island views, Brooklyn Bridge pass, and skyline sailing.

★ 4.5

“My girls were able to help raise the sail and were able to “captain” for a few minutes! Double check sail times on Web site. We had to wait an extra hour because the viator site was wrong. Crew was very kind about the confusion.”

264 reviews1 hour 30 minutes (approx.)From $68.00by Manhattan By Sail

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NYC: City Lights Yacht Cruise with Drink Included

/ August 16, 2026

10.NYC: City Lights Yacht Cruise with Drink Included

NYC City Lights yacht cruise from Chelsea Piers with 1 free drink. See Lower Manhattan and the Statue of Liberty at night.

★ 4.8

“This was a great kick off activity for our NY trip. Hot summer eve out on the water, beautiful views of the city skylines, and sites. Excellent cocktails, romantic setting. The only con was not being able to hear the captain point out the sites, as we opted to sit outside. Still a lovely outing.…”

241 reviews75 - 90 minutesFrom $78by Classic Harbor Line - New York City

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NYC: Statue of Liberty Day Sail on the Schooner Adirondack

/ August 27, 2026

11.NYC: Statue of Liberty Day Sail on the Schooner Adirondack

Sail the Statue of Liberty from the Schooner Adirondack. 105 minutes of New York Harbor views and one included drink.

★ 4.9

“Beautiful day, knowledgeable and enthusiastic crew, generous refreshments”

182 reviews1.8 hoursFrom $60by Classic Harbor Line - New York City

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2.5-hour Guided Sailboat Tour

/ August 27, 2026

12.2.5-hour Guided Sailboat Tour

A small-group sail from Brooklyn for close-up Statue of Liberty views, skyline passes, and real harbor time in about 2.5 hours.

★ 5.0

“Such a wonderful experience! Ian is very friendly and professional - was an absolute pleasure. Thank you and I’m definitely going to plan another trip, soon.”

181 reviews2 hours to 2 hours 30 minutes (approx.)From $118.00by Brooklyn Sail

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