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Captain
All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 372 listings

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
A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups
Sailing in Sag Harbor · 25 guests

A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

5.0
$600hour
Classic sailboat in the heart of NYC.
Sailing in Manhattan · 6 guests

Classic sailboat in the heart of NYC.

5.0
$330hour
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160hour
Luxury 49ft Sailing Yacht Charter in NY Harbor - US Coast Guard Inspected
Sailing in Manhattan · 12 guests

Luxury 49ft Sailing Yacht Charter in NY Harbor - US Coast Guard Inspected

5.0
$700hour
Sailing Long Island Sound with Captain Steve
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve

5.0
$199hour
Sail from Jersey City, NJ - $265/Hour - $44/Person
Sailing in Manhattan · 6 guests

Sail from Jersey City, NJ - $265/Hour - $44/Person

5.0
Superowner
Best of 2023
$265hour
Jeanneau 39i Julia Sailing Yacht in NY Harbor
Sailing in Manhattan · 6 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$350hour
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
$150person
Tanzer 26' Small Sailboat for Day in Charlotte
Sailing in Charlotte · 6 guests

Tanzer 26' Small Sailboat for Day in Charlotte

5.0
$350day
Sail From Port Washington, NY - $219/Hour - $37/Person
Sailing in Port Washington · 6 guests

Sail From Port Washington, NY - $219/Hour - $37/Person

4.7
Superowner
Best of 2023
$37person
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
Sailing in Manhattan · 6 guests

Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

5.0
$224-$298hour
27  feet of fun in the summer sun, under sail!
Sailing in Brooklyn · 6 guests

27 feet of fun in the summer sun, under sail!

New
Snoozed - Active 02 Jun 2024
1976 Classic Sailboat Charter out of Burlington Harbor
Sailing in Burlington · 4 guests

1976 Classic Sailboat Charter out of Burlington Harbor

5.0
$80-$100hour
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$129hour
Experience premiere service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premiere service: NYC’s longest-running private sailing charter

5.0
$370hour
35ft Cycleboat Party Boat Rental in Hoboken, New Jersey
Powerboats in Manhattan · 26 guests

35ft Cycleboat Party Boat Rental in Hoboken, New Jersey

5.0
$499hour
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Events in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$350hour
Enjoy Lake Simcoe on Lowe Cruise 1600 Pontoon!
Powerboats in Georgina · 7 guests

Enjoy Lake Simcoe on Lowe Cruise 1600 Pontoon!

5.0
$65hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125hour
A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests
Sailing in Sag Harbor · 41 guests

A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests

5.0
$1,250hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,800hour
Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!
Sailing in Brooklyn · 4 guests

Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!

5.0
$180hour

Sailing Reviews in New York

  1. VY

    Veronica

    Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

    I’d like to 100% recommend you to get a boat trip with Dave - he is a very experienced, responsible captain - you’ll definitely enjoy it!

  2. Sydney

    Sydney

    Classic sailboat in the heart of NYC.

    This was the perfect surprise birthday gift for my boat loving fiancé. We did the 5:30-7:30pm sail and it was so much fun! The Captains were incredible welcoming and accommodating. We got to choose where we sailed to. My fiancé even got to take the wheel and relive his sailing glory days. I cannot recommend this experience enough for your family, friends or co-workers!

  3. FU

    Fred

    Classic sailboat in the heart of NYC.

    Captain David was very helpful and friendly. The boat was reserved for a special occasion and the captain accommodated all of our requests. All around very satisfied with the level of professionalism and attitude. Thank you for a great ride and letting me steer.

  4. WB

    Wayne

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    I really appreciate how Captain Nina accommodated me last minute after I had a lesson scheduled at a sailing school. Saved my plans for the weekend. She did a great job adjusting the experience to my level, and keeping the whole time chill and conversational.

  5. Megan

    Megan

    Luxury 49ft Sailing Yacht Charter in NY Harbor - US Coast Guard Inspected

    We had the best time celebrating my husbands 30th birthday. The boat was comfortable and clean with everything we needed. The bluetooth speaker system was brilliant and easy to use. Communication with the team leading up to depature was fantastic, we will definitely be back again in the future!

  6. KS

    Katherine

    Sailing Long Island Sound with Captain Steve

    Steven was an excellent host! He answered all of our questions up to the trip and met us on the dock when we got there. The boat was great and the trip was exciting, he even let us help sail! All the views were great and we loved the whole experience!