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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,235 Reviews)

Page 8 of 40938 listings

Limited Availability
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
$475/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
Your own 42' Private Sailboat in Cabo
Sailing in Marina · 14 guests

Your own 42' Private Sailboat in Cabo

5.0
Superowner
Best of 2026
$363/hour
Sailing Trips out of La Conner, Washington
Sailing in Anacortes · 8 guests

Sailing Trips out of La Conner, Washington

5.0
$500/day
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
3-hour exclusive Catamaran Sunrise or Sunset
Sailing in Isla Mujeres · 16 guests

3-hour exclusive Catamaran Sunrise or Sunset

4.9
Superowner
$262/hour
44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$520/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
$1,000/day
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,
Events in Marina · 12 guests

Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,

5.0
$350/hour
Gorgeous Luxurious Catamaran Open Bar
Sailing in Cancún · 30 guests

Gorgeous Luxurious Catamaran Open Bar

5.0
$327/hour
37ft Sea Ray Sundancer Yacht for Charter  in Cabo San Lucas, Baja California Sur
Events in Marina · 8 guests

37ft Sea Ray Sundancer Yacht for Charter in Cabo San Lucas, Baja California Sur

5.0
$230/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
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Marlowe Hunter 33’ Sailing In Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing In Fort Lauderdale

5.0
$90+/hour
Limited Availability
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Create Memories you will Cherish for Life on this 47' Luxuary Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxuary Sailboat!

5.0
Superowner
$200+/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
$300+/hour
High Demand
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
Lagoon 42 Yacht Catamaran In Punta Mita
Sailing in Punta de Mita · 20 guests

Lagoon 42 Yacht Catamaran In Punta Mita

5.0
Superowner
Best of 2026
$309+/hour
Instant Book
Limited Availability
Destination yacht Rental in Peoria, Arizona
Powerboats in Peoria · 20 guests

Destination yacht Rental in Peoria, Arizona

4.5
Superowner
$375/hour
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour

Sailing Reviews in United States

  1. BA

    Brianne

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    We had the the most beautiful sunset cruise with Brian and their catamaran. Beyond accommodating, easy to communicate with, and a beautiful space. We had a group of 12 girls, and we felt more than comfortable relaxing, being silly- and not to mention the endless photos we asked to take. Everything you need on board with freedom to bring what you like. I could not suggest booking with Brian more!

  2. JP

    Jenny

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    I can’t say enough about how great this experience was! I celebrated my birthday, and it will definitely be one of the most memorable ones. The boat was beautiful, clean, and spacious. The best part was having Captain Rick on board. He was knowledgeable, kind, and made us feel very comfortable the entire time. He showed us around, shared interesting information, and made sure we had a smooth and relaxing sailing trip. Truly an unforgettable experience!

  3. PC

    Peter

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

  4. SK

    Sean

    Puget Sound Sailing Adventure on 32' Hunter Sailboat

    Russ was outstanding from start to finish. Such an incredible human and captain. Our family spent 3 beautiful hours filled with incredible beauty and wonderful conversation with Russ. It exceeded all of our expectations and was a perfect way to escape the chaos and enjoy the tranquil vibes of the ocean. Top notch from start to finish. We highly recommend Russ and Dylan.

  5. Kelly

    Kelly

    Well Appointed Beneteau 32, Folly Beach, SC

    Greg is an amazing captain!! He’s chill, fun, and so accommodating! We used the boat for our engagement pics and he couldn’t have been nicer to us and our photographer. We would definitely go on his boat again in a heartbeat!!!

  6. AG

    Ashley

    FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

    Drew was amazing! He was knowledgeable, communicative, and professional. We had a great time. Definitely recommend spinnaker sailing!!!