Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,218 Reviews)

Page 9 of 40939 listings

Gorgeous Luxurious Catamaran Open Bar
Sailing in Cancún · 30 guests

Gorgeous Luxurious Catamaran Open Bar

5.0
$326/hour
Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/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
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
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/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
Marlowe Hunter 33’ Sailing In Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing In Fort Lauderdale

5.0
$90+/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
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
DAYTRIP/SLEEP ON BOARD TO CATALINA
Sailing in Los Angeles · 12 guests

DAYTRIP/SLEEP ON BOARD TO CATALINA

4.9
Superowner
$199/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
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in San Miguel de Cozumel · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$270+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat

5.0
$2,500/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way
Events in Cancún · 20 guests

Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way

4.8
$330/hour
Instant Book
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

5.0
Superowner
$480/hour
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

5.0
$165/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour

Sailing Reviews in United States

  1. 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.

  2. WD

    William

    6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

    My friends and I had a great time cruising around the bay with Ryan. The boat is fast and a great way to get around the bay while taking in the sun and sights.

  3. 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!!!

  4. BH

    Bibiana

    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

    We are still talking about our time aboard The Genesis! Eric was so welcoming to our family, ages 2 - 70! A true sailor, Eric took us on a two-hour sail from Chelsea Piers to the Statue of Liberty. He shared his endless knowledge about NYC as we passed spots of interest on the shoreline. Eric was super kind and patient with our 5-year-old grandson, allowing him to steer the boat. That experience was priceless. The Genesis is a wonderful sailboat that has been lovingly and meticulously cared for. Thank you, Eric, for helping us celebrate Nick's 70th birthday. It was perfect!

  5. JH

    Jeremy

    Gorgeous Luxurious Catamaran Open Bar

    The Trip was amazing. Great Staff Great food, Great service. Would Highly recommend this charter and this Captain. All of my passengers loved every minute of this. A+++

  6. DG

    David

    Gorgeous Luxurious Catamaran Open Bar

    The experience was simply great! The crew was amazing, the boat just perfect! And the day wondefull! 100% recommended. Listen Tatyana recomendations, she almost beg us to upgrade the size of the boat for the amount of people we were. Best recomendation ever! Thanks