
New York Harbor Wine and Jazz Sail aboard Clipper City
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.2/5
Based on 24 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is New York Harbor Wine and Jazz Sail aboard Clipper City worth booking?
New York Harbor Wine and Jazz Sail aboard Clipper City is a 1.8-hour experience in New York, United States, from $48 per person. It scores 55 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.2/5 rating across 24 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 55 / 100
- Rating
- 4.2/5 (24)
- Duration
- 1.8 hours
- From
- $48 per person
Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glittering before you—a view that captures New York at its very best. More than a cruise, this is an homage to the owner’s Ne
What you get
About this experience
Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glittering before you—a view that captures New York at its very best. More than a cruise, this is an homage to the owner’s New York jazz roots, brought to life by a rotating cast of the city’s most accomplished musicians. From smoky ballads to bebop, swing, American standards, and straight-ahead jazz, the music flows seamlessly with the rhythm of the harbor. On deck, the Clipper City channels the cozy elegance of Bemelmans and the iconic energy of the Monkey Bar—intimate, timeless, and full of charm. With up to two glasses of wine included, plus a full bar on board, it’s the ultimate way to celebrate, impress, or simply lose yourself in the magic: sailing aboard New York’s largest Tall Ship, set against the dazzling backdrop of the world’s most vibrant city. A night that feels authentically New York—sophisticated and alive, relaxed yet unforgettable.
What travelers are saying
Outty’s summary of the themes that recur across 24 traveler reviews. Written by us, not quoted from reviewers.
Photo opportunities
4 mentionsThe views and photo stops come up again and again.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Pace and timing
2 mentionsSeveral reviewers comment on how the schedule is paced.
Traveler reviews
24 verified traveler reviews for New York Harbor Wine and Jazz Sail aboard Clipper City. Ratings and reviews provided by Viator and Tripadvisor.
Book at risk and review Cancellation policy first!
Be careful with booking. I have no doubt it would have been a beautiful experience but if by chance (which was the case with me) the sail is cancelled by the company you will not get a refund but a proposed new date to sail. I am not from the area so was unable to book another time thus am out the $275.
via Tripadvisor
Memorable evening trip past lady liberty
Glorious summer evening with s beautiful sunset, great music and friendly crew
via Tripadvisor
Bad experience
Cancelled hours before. Totally unprofessional. Gave us an option for an earlier time (before sunset) or following day, neither of which worked with our child care provider.
via Viator
Sailing experience in Manhattan
Nice experience if you have the a pass like the new York pass. They sail to statue of Liberty and back. They do not turn off the engine during the trip so is not 100% sailing experience but is ok
via Tripadvisor
Amazing Experience
Amazing experience! We were ready-booked to another one of their boat on the west side and it was such a nice experience for our anniversary. Not crowded at all and very relaxing. Staff was 💯. Super nice and welcoming
Response from the operator: Great to have you on board! Hope to see you again soon.
via Tripadvisor
Good to know
- Duration
- 1.8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 8
- Verdict
- Worth a Look
Why this scores 55
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
New York Harbor Wine and Jazz Sail aboard Clipper City: questions travelers ask
Practical detail on this experience, plus the wider planning questions for New York.
How much does New York Harbor Wine and Jazz Sail aboard Clipper City cost?
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Prices start at $48 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in New York usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does New York Harbor Wine and Jazz Sail aboard Clipper City take?
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Plan for about 1.8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in New York is not rushed.
Is New York Harbor Wine and Jazz Sail aboard Clipper City worth it?
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It holds an Outty Ranking of 55 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.2/5 across 24 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in New York, and how flexible the cancellation terms are.
Can I cancel or reschedule New York Harbor Wine and Jazz Sail aboard Clipper City?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is New York Harbor Wine and Jazz Sail aboard Clipper City suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book New York Harbor Wine and Jazz Sail aboard Clipper City?
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Around 8 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in New York can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in New York and add a light layer if any part of the 1.8-hour experience runs outdoors or after sunset.
Where does New York Harbor Wine and Jazz Sail aboard Clipper City start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central New York within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in New York?
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New York has more bookable experiences than any other city on Outty, and the quality spread is brutal. Observation decks are commoditised, so we score them on timed-entry reliability and sunset slots. Food tours and borough walks are where the ranking really separates operators, and the top scores in the city all come from small-group guides. On Outty we rank every New York experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Grand Canyon VIP Helicopter Tour, Half-Day Bus Tour of NYC Top Highlights, NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit New York?
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September to early November, and late April through June. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in New York?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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