We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 475 listings

 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
$255-$285hour
Instant Book
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Sailing in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

5.0
Superowner
$37person
#1 Manhattan Sailboat! 5-Star Service with Captain, Crew, Champagne & Catering
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! 5-Star Service with Captain, Crew, Champagne & Catering

5.0
Superowner
Best of 2023
$335hour
27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$55person
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Sailing in Manhattan · 6 guests

Woman-owned luxury with transparent pricing - read our 5-star reviews!

5.0
$285hour
56' Sea Ray Sedan Bridge in New York!
Events in Brooklyn · 12 guests

56' Sea Ray Sedan Bridge in New York!

4.7
$475hour
Sail from Norwalk, CT - $220/Hour - $37/Person
Sailing in Norwalk · 10 guests

Sail from Norwalk, CT - $220/Hour - $37/Person

4.6
Superowner
Best of 2023
$36person
Caribbean Vibez SPECIAL $220 x 2 hrs August 16th , 17th and 18th on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez SPECIAL $220 x 2 hrs August 16th , 17th and 18th on a Brooklyn Sailboat

5.0
Superowner
$191hour
Sail New York's historic waterways aboard Water Music, a classic, semi-custom 40 foot Passport yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic, semi-custom 40 foot Passport yacht.

5.0
Snoozed - Active 02 Jul 2024
Sailing Charter in Toronto
Sailing in Toronto · 6 guests

Sailing Charter in Toronto

5.0
$73person
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$325hour
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$183hour
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$275hour
Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person
Sailing in Huntington · 6 guests

Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person

5.0
Superowner
Best of 2023
$50person
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
Superowner
Best of 2023
$475hour
Sailing NYC with Brooklyn Sail
Sailing in Manhattan · 6 guests

Sailing NYC with Brooklyn Sail

5.0
Superowner
$220hour
K25 Racing Boat Clarisse
Sailing in Mississauga · 5 guests

K25 Racing Boat Clarisse

5.0
$59hour
A Tropical Experience on a Massive Sailing Trimaran
Sailing in Toronto · 12 guests

A Tropical Experience on a Massive Sailing Trimaran

4.9
$330hour
Charter 38' Pearson Cruising Monohull In Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

5.0
$100person
Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

5.0
$300hour
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$285hour
Beautiful Trimaran for 10 People in Toronto
Sailing in Toronto · 12 guests

Beautiful Trimaran for 10 People in Toronto

5.0
$293hour
46ft Hunter Sailing Yacht Rental in Brooklyn, NY - $295/Hour
Sailing in Manhattan · 6 guests

46ft Hunter Sailing Yacht Rental in Brooklyn, NY - $295/Hour

5.0
Superowner
Best of 2023
$295hour

Sailing Reviews in New York

  1. Lisa

    Lisa

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Rick you made our first wedding anniversary so special. Thank you for your suggestion to dine and dock, your knowledge on the history of the area and for your great sense of humor! We had a great time! Nirvana is such a beautiful vessle

  2. VS

    Vaibhav

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian was fantastic! Ian explained everything in detail and was very welcoming. I really enjoyed the experience and hospitality. I wanted to surprise my partner with the trip, and Ian was very accommodating in trying to keep it as last minute as possible. The boat was very well maintained and the ride was extremely smooth. Ian helped me create memories that'd last a lifetime and for that I'd highly recommend him.

  3. VL

    Van

    Sailing NYC with Brooklyn Sail

    It's a bit windy but we all enjoyed the view and how friendly and professional Andrew is. He was very kind in helping my friend who has sea sickness. I had a wonderful birthday today on the boat even though it was cold. Also, they kindly waited for me to arrive due to unexpected traffic jam.

  4. SC

    Susanna

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Thank you Ian! Ian was professional and kind. We had the best time celebrating my partner’s birthday! A night our group will remember for a long time.

  5. Shannon

    Shannon

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    My fiancé & I had our engagement photoshoot on board. I can’t rave enough about how wonderful of an experience that we had. Ian and Kim were both incredibly friendly and professional. 10/10. We will definitely be renting from them again in the near future!

  6. JK

    Jay

    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

    Eric is an absolute professional. We could not have asked for a better captain - what makes him special is that he's truly passionate about what he does.