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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,226 Reviews)

Page 20 of 40938 listings

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
Sailing in Nassau · 12 guests

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

5.0
$1,375/hour
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
Sailing Lessons in Valle de Bravo
Tours in Valle de Bravo · 5 guests

Sailing Lessons in Valle de Bravo

5.0
$87/hour
45ft  Luxury Catamaran Private Charter / Capacity 38 people
Sailing in Cancún · 40 guests

45ft Luxury Catamaran Private Charter / Capacity 38 people

New
Superowner
$572+/hour
Best 75ft Catamaran in Cancun and Isla Mujeres! Holds 100 people
Sailing in Cancún · 100 guests

Best 75ft Catamaran in Cancun and Isla Mujeres! Holds 100 people

5.0
$842+/hour
Sailboat Odyssey 46 Luxury Sailing In Cancun, Mexico
Sailing in Isla Mujeres · 10 guests

Sailboat Odyssey 46 Luxury Sailing In Cancun, Mexico

5.0
$217+/hour
50Ft Sunseeker Yacht Perfect for your Party 🎉
Events in Marina · 10 guests

50Ft Sunseeker Yacht Perfect for your Party 🎉

New
$270/hour
40' Catamaran - Sail away
Sailing in Marina del Rey · 6 guests

40' Catamaran - Sail away

5.0
$400/hour
Rent our 25ft Sailboat in Kemah, Texas
Sailing in Seabrook · 4 guests

Rent our 25ft Sailboat in Kemah, Texas

5.0
$54/hour
"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo
Sailing in Tamarindo · 70 guests

"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo

5.0
$532/hour
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2026
$75/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,900/hour
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350/hour
46ft Sailing Catamaran Private Charter / Capacity 45 people
Sailing in Cancún · 45 guests

46ft Sailing Catamaran Private Charter / Capacity 45 people

3.3
Superowner
$343+/hour
Cabo San Lucas Private 28ft Yacht Tour with Snorkel
Events in Marina · 8 guests

Cabo San Lucas Private 28ft Yacht Tour with Snorkel

New
$255/hour
Experience the Gulf Star 41' Sailing and Dining in Guanacaste
Sailing in Guanacaste Province · 12 guests

Experience the Gulf Star 41' Sailing and Dining in Guanacaste

5.0
$200/hour
Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 45 guests

Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica

5.0
$750/hour
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 12 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$400+/hour
Private 45ft Catamaran Yacht In Cabo | All-Inclusive Food and Open Bar
Powerboats in Marina · 20 guests

Private 45ft Catamaran Yacht In Cabo | All-Inclusive Food and Open Bar

New
$759+/hour
Sailing Charter, 42 ft Cutter Ketch snorkeling, scuba. Roatan Honduras
Sailing in Bay Islands Department · 6 guests

Sailing Charter, 42 ft Cutter Ketch snorkeling, scuba. Roatan Honduras

5.0
$600/day
Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat
Sailing in Berkeley Township · 6 guests

Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat

New
$125/hour
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour
3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston

New
$250/hour
Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston

New
$250/hour

Sailing Reviews in United States

  1. DF

    Dina

    Rent our 25ft Sailboat in Kemah, Texas

    Loved the sailing experience on the 25 foot sailboat. Eventhough it was an old sailboat form the 80's, David, our captain, was in control of every detail. He is a great captain. He is very paused and confident and easy to get along with. Recommend David with closed eyes. Lucy and the rest of the gals at the office are great people.

  2. LC

    Louis

    Experience the Gulf Star 41' Sailing and Dining in Guanacaste

    Incredible sailing experience, look no further and book. From start to finish Hugo and the fellow two crew members were incredible guides, and the itinerary they drafted was spectacular. Great value and every step of the way was incredible. Food and drinks very good as well, and a very safe experience. Also compared to other options the best value in Guanacaste. Will be back!!

  3. Ryan

    Ryan

    Sailing Lessons in Valle de Bravo

    Great experience. I sent a booking request overnight and got a response first thing in the morning. The captain was knowledgeable and professional. Spanish Language.

  4. KB

    KAREN

    Experience the Gulf Star 41' Sailing and Dining in Guanacaste

    Hugo's sailing trip was the perfect fit for our group of 5, varying in all ages and activity levels. We were able to customize our tour to fit what we were looking for.

  5. KC

    Katie

    Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica

    We had the best time for my 40th birthday w/ 19 ppl . The food was excellence. The staff was great and the boat was perfect. Just take me back again please!

  6. AN

    Anna

    Classic Yacht Charter in New York, New York

    James was great, his communication ahead of our sailing day was on point and him and his crew provided an unforgettable experience for our team.