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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,283 Reviews)

Page 1 of 40938 listings

Fun time Jet Ski Rental at Lake Norman, NC near Charlotte
Water Sports in Cornelius · 8 guests

Fun time Jet Ski Rental at Lake Norman, NC near Charlotte

5.0
$90/hour
35' Private Catamaran Charters in Belize
Sailing in San Pedro · 16 guests

35' Private Catamaran Charters in Belize

5.0
$130/hour
Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
$110+/hour
30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/hour
Private 30’ Catalina Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Private 30’ Catalina Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$2,500/hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
$600/hour
Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel
Sailing in West Bay · 20 guests

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel

5.0
$400/hour
Cancun Private Catamaran Isla Mujeres - Open Bar, Snorkeling Lunch & Fun
Sailing in Cancún · 15 guests

Cancun Private Catamaran Isla Mujeres - Open Bar, Snorkeling Lunch & Fun

5.0
Superowner
$169/hour
23’ Bayliner Beautiful Boat In Miami
Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

4.9
$90/hour
 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
New in the bay! Lagoon 42' Sailing Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

New in the bay! Lagoon 42' Sailing Catamaran in La Cruz

5.0
Superowner
Best of 2026
$250+/hour
Instant Book
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
$200/hour
Crown 34' Sailboat - Private Coastal Sailing - Los Angeles
Sailing in Marina del Rey · 4 guests

Crown 34' Sailboat - Private Coastal Sailing - Los Angeles

4.9
$120/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2026
$213+/hour
Lagoon 450F Catamaran
Sailing in George Town · 30 guests

Lagoon 450F Catamaran

5.0
$500/hour
46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

5.0
Superowner
Best of 2026
$599/hour
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
Superowner
$355/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
Lagoon 40 Yacht Catamaran in Puerto Vallarta
Sailing in Marina Vallarta · 15 guests

Lagoon 40 Yacht Catamaran in Puerto Vallarta

5.0
Superowner
Best of 2026
$225+/hour
Instant Book
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
$59/hour
William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience
Sailing in Seattle · 8 guests

William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience

5.0
$150/hour
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
Private 40ft Lagoon Catamaran -  Isla Mujeres | Open Bar, Snorkeling & Lunch
Sailing in Cancún · 30 guests

Private 40ft Lagoon Catamaran - Isla Mujeres | Open Bar, Snorkeling & Lunch

5.0
Superowner
$249/hour
All-Inclusive Sunset Cruise in Cabo San Lucas
Tours in Marina · 45 guests

All-Inclusive Sunset Cruise in Cabo San Lucas

5.0
Superowner
Best of 2026
$350/hour

Sailing Reviews in United States

  1. LT

    Luc

    William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience

    Shiva was an incredible captain! Super knowledgeable about sailing, and he made the entire experience super special for my wife and I. He’ll tailor the experience to your preferences — whether you want to stay on the water to dock to drink some wine and explore! Don’t hesitate to book with him and his beautiful sailboat.

  2. KL

    Kisha

    46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

    This was such a fun, enjoyable experience. From transportation to the water stop, we had a great time. Your staff was amazing ,courteous, and attentive. They were the highlight of the boat as they made the entire experience a 10/10! The service was amazing! I would definitely recommend this excursion to anyone visiting Jamaica. Will definitely book this service again next time! Thank you guys for such a great time.

  3. piero

    piero

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    what a guy, amazing experience. don’t look further 11/10 worth it. really knowledgeable laidback and overall careful on sailing. you can tell he really cares for his passengers. let me steer for a bit and enjoy the moment. I truly have no words what an amazing one of a kind experience.

  4. ME

    Maddie

    FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

    Captain Johnny was absolutely wonderful! Booked for a bachelorette trip and it was such a fantastic time. Spent some time in the sand, on the water and saw some native aquatic life. Could not recommend enough!

  5. KR

    Karina

    Lagoon 40 Yacht Catamaran in Puerto Vallarta

    Everything about our trip was amazing. The attention from each crew member was exquisite!! They made sure we were comfortable and took care of us at all times. Truly the best in PV!

  6. EN

    Emma

    30ft Catalina Sailboat Charter in Alameda CA

    My friends & I had a great trip with Brad for 6! We didn’t expect him to let us actually sail with him, but it was super informative. He was very knowledgeable about the boat and navigating other boats. Everything was clean! We were able to bring our own food & drinks too! We would definitely recommend it to others in the future!!