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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,234 Reviews)

Page 1 of 40938 listings

Limited Availability
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/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
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
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
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
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
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
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
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
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
Lagoon 450F Catamaran
Sailing in George Town · 30 guests

Lagoon 450F Catamaran

5.0
$500/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
Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur
Sailing in Zona Comercial · 6 guests

Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur

5.0
$120/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
Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 25 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$435/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$270+/hour
Sail in Modern Luxury Beneteau Oceanis 37 Yacht
Sailing in Oceanside · 6 guests

Sail in Modern Luxury Beneteau Oceanis 37 Yacht

5.0
$175/hour
34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas
Events in Marina · 8 guests

34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas

5.0
$190/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/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
Limited Availability
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
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

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. BC

    Bryan

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

    Aaron was super fun and extremely knowledgeable. Our group of five has so much fun sailing the rougher, windier seas. We then made for a secluded spot to fish and swim while we waited for sunset. It was a glorious view and truly checked off a bucket list item for me. Bryan - Oregon

  6. RC

    Robin

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

    an hour ago New This team was very accommodating and thoughtful! They provided our family with a safe, fun, wonderful experience. They are very kind and extremely attentive. They even helped us make a loving tribute to a family member who could not be with us. The food, drinks, and scenery were wonderful. I wouldn't hesitate to book with them again! They take great care of people!