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Find Sailing Charters Near You

4.9
(4,939 Reviews)

Page 5 of 10240 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
Best of 2026
$240+/hour
Caribbean Vibez on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez on a Brooklyn Sailboat

5.0
Superowner
$191/hour
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
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
$150/hour
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$178/hour
Sailing Lesson in Little River, South Carolina
Tours in Little River · 1 guest

Sailing Lesson in Little River, South Carolina

New
$360/hour
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
2 Hour Sunset Sail in Wrightsville Beach
Sailing in Wrightsville Beach · 6 guests

2 Hour Sunset Sail in Wrightsville Beach

New
$175/hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/hour
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$150/hour
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$150/hour
Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC
Sailing in Wilmington · 6 guests

Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

5.0
$350/hour
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
$50/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$190+/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
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
$160/hour
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
$85/hour

Local Sailing Reviews

  1. RR

    Roberto

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian was amazing, very friendly and caring. Can’t wait to do it again Thanks

  2. JB

    Joshua

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Great communicator; amazing route and accurate listing. Definitely recommended.

  3. Maria

    Maria

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We had an absolutely perfect experience with our captain! From start to finish, everything was seamless—professional, friendly, and so attentive. The boat was in excellent condition, and the captain made us feel safe and comfortable the entire trip. His knowledge of the area and smooth handling of the boat made the day unforgettable. We couldn’t have asked for a better experience. Highly recommend!

  4. MS

    Megan

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We celebrated our 10th anniversary on Faith and couldn’t be happier. Captain Ian personalized the journey for us and guided us along the way. He was exuberant, caring, and checked in with us to make sure we were having a great time. He asked if we wanted to learn sailing and taught us a few things, which was so cool and unexpected. We are excited to sail again to learn more and see the beautiful sites NYC has offer!

  5. AS

    Andie

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian and Kim were fantastic hosts, captain and first mate! We used Ian’s vessel for a music video shoot, and not only were they helpful and accommodating, but happy to have us aboard and a part of our production. I highly recommend booking with Ian for a similar situation or if you just wanted a fun outing with some good friends!

  6. GS

    Gurpreet

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian did a great job with our trip. He was able to show us all around nyc and even though we were running close to the sunset, he was able to get us out on the water in time to watch. The boat ride was smooth, he was very accomodating. It was fun chatting with him and he came prepared with blankets, jackets, water if needed. The boat trip itself was smooth with no issues. Would definitely book again, if needed and highly recommend!