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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,047 Reviews)

Page 20 of 39918 listings

MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
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
38ft Leopard Catamaran in Cape Canaveral
Sailing in Cape Canaveral · 6 guests

38ft Leopard Catamaran in Cape Canaveral

5.0
$250/hour
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
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/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
$844+/hour
Sailing Lessons in Valle de Bravo
Tours in Valle de Bravo · 5 guests

Sailing Lessons in Valle de Bravo

5.0
$87/hour
40' Catamaran - Sail away
Sailing in Marina del Rey · 6 guests

40' Catamaran - Sail away

5.0
$400/hour
Beneteau 41.1 Oceanis Sailing Charter in Vancouver
Sailing in Vancouver · 6 guests

Beneteau 41.1 Oceanis Sailing Charter in Vancouver

5.0
$366/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
Rent our 25ft Sailboat in Kemah, Texas
Sailing in Seabrook · 4 guests

Rent our 25ft Sailboat in Kemah, Texas

5.0
$54/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
"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
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
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2026
$75/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
Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch
Powerboats in Sosúa · 70 guests

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

New
$242/hour
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

New
$225/hour
Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 12 guests

Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC

New
$292/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
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
Private Sunset Catamaran Cruise Cabo San Lucas for 50 Guests
Sailing in Ildefonso Green · 50 guests

Private Sunset Catamaran Cruise Cabo San Lucas for 50 Guests

New
$890/hour
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/hour
Bahia de las Aguilas- Private Catamaran Cruise
Events in Dominican Republic · 70 guests

Bahia de las Aguilas- Private Catamaran Cruise

New
$500/hour

Sailing Reviews in United States

  1. Ryankeisha

    Ryankeisha

    Private Group Sail and Snorkel Montego Bay

    My crew and I really enjoyed our boat ride and the Excursions that went along with it. We had lots of fun and the captain, my co-captain, and crew were very entertaining and accommodating. The food was delicious and the drinks were continuously flowing. I will definitely come back and do it again.

  2. 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.

  3. 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!!

  4. MG

    Matt

    38ft Leopard Catamaran in Cape Canaveral

    Thank you for a great day on the water. We weren't sure what to expect, but the up and down of the the xalm waters of the canal and river provided a relaxing and pleasant experience.

  5. 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.

  6. 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.