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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,261 Reviews)

Page 1 of 40946 listings

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
$155+/hour
Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$136/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
Best of 2025
$600/hour
Private Coastal Sailing - Los Angeles
Sailing in Marina del Rey · 4 guests

Private Coastal Sailing - Los Angeles

4.8
$95/hour
22ft Sea Fox 226 Commander for Family fun or Fishing!
Powerboats in Tavernier · 8 guests

22ft Sea Fox 226 Commander for Family fun or Fishing!

5.0
$65/hour
30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/hour
35' Private Catamaran Charters in Belize
Sailing in San Pedro · 16 guests

35' Private Catamaran Charters in Belize

4.9
$130/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 2025
$240+/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2025
$200/hour
Private Catamaran - Sailing To Isla Mujeres
Sailing in Cancún · 15 guests

Private Catamaran - Sailing To Isla Mujeres

5.0
Superowner
Best of 2025
$169/hour
Instant Book
38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.
Sailing in Puerto Aventuras · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.

5.0
Superowner
$420/hour
⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

5.0
Superowner
Best of 2025
$250+/hour
Instant Book
46 feet luxury yacht in Montego Bay with unlimited cocktails
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with unlimited cocktails

5.0
Superowner
Best of 2025
$599/hour
The Only 40ft Hinckley Sailboat in Manhattan
Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan

5.0
$345/hour
Instant Book
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
$450/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$253+/hour
Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta

4.7
Best of 2025
$124/hour
Fun time Jet Ski Rental at Lake Norman/Lake Wylie, SC near Charlotte, NC
Water Sports in Cornelius · 8 guests

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

4.9
$84+/hour
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/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
$250/hour
Spacious, fast 80 foot sailboat with a hot tub
Events in Marina Vallarta · 40 guests

Spacious, fast 80 foot sailboat with a hot tub

5.0
$275/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 2025
$225+/hour
Instant Book
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95+/hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour

Sailing Reviews in United States

  1. SS

    Stephanie

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    Mason and Lynne were amazing captains on a private sail charter! So easy to communicate with throughout my planning process and amazing people overall! Had a great time being on the boat with them! Would absolutely recommend them and this experience!

  2. CL

    Chloe

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    We booked the full-day rental for a bachelorette party and had a wonderful time. Amory was very responsive, answered all of our questions, and even offered to decorate the boat for the celebration. The crew on board was nice and attentive throughout the day. The catamaran itself was spacious with plenty of room for our group of 10, and one of the girls especially loved how comfortable the bed was for a nap. The highlight of the day was the beautiful sunset on the ride back, an unforgettable experience!

  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. JS

    Jonathan

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.

  5. KS

    Kenneth

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    From the beginning of the booking process to the day of the experience, Amory and his team were completely professional, knowledgeable, accommodating, and a complete joy to sail with. I’d highly recommend this company. I’d also book again! They were a 10 out of a 10! We all had a blast.

  6. LP

    Lolly

    The Only 40ft Hinckley Sailboat in Manhattan

    I highly recommend chartering Captain Andy's sail boat! Everything in the listing was exactly as described and his boat was perfect for a day on the water. He answered all of our (admittedly dumb) questions about NYC and was super friendly and took plenty of photos of us when asked. I have no complaints and would definitely charter Captain Andy's boat again!