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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,390 Reviews)

Page 20 of 38889 listings

Fairhaven/New Bedford - Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 6 guests

Fairhaven/New Bedford - Sail Buzzards Bay in a Classic Sloop!

5.0
$150/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
$75+/day
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
$712/hour
Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay
Sailing in Marina Vallarta · 12 guests

Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay

New
Superowner
Best of 2025
$459/hour
52 Luxury Catamaran With Ac - Rates For 2 People
Sailing in Guna Yala Comarca · 8 guests

52 Luxury Catamaran With Ac - Rates For 2 People

5.0
$2,540/day
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2025
$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
Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat
Sailing in Montego Bay · 14 guests

Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat

New
$250/hour
50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!
Sailing in Miami Beach · 42 guests

50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

New
Superowner
Best of 2025
$850/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
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
$285/hour
Manuel Antonio Catamaran Private ''Spanish Dancer''
Sailing in Quepos · 12 guests

Manuel Antonio Catamaran Private ''Spanish Dancer''

5.0
$1,500/hour
''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0
$382/hour
Custom 40ft Sail Boat Rental in Cozumel
Sailing in Centro · 12 guests

Custom 40ft Sail Boat Rental in Cozumel

New
$168/hour
Clear Kayak Mangrove Cay Eco Venture 2-hour tour
Adventures in Leeward Settlement · 10 guests

Clear Kayak Mangrove Cay Eco Venture 2-hour tour

New
$200/hour
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450/hour
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

New
Best of 2025
$175+/hour
Amazing 36' Catamaran in Puerto Aventuras, closest marina from Tulum
Sailing in Puerto Aventuras · 18 guests

Amazing 36' Catamaran in Puerto Aventuras, closest marina from Tulum

5.0
$325/hour
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/hour
😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
Events in Sosúa · 18 guests

😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

New
Superowner
Best of 2025
$75/hour
5⭐️ Lagoon 40’ 2016 All inclusive
Sailing in Centro · 20 guests

5⭐️ Lagoon 40’ 2016 All inclusive

New
Superowner
$457/hour
30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter
Sailing in Cancún · 30 guests

30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter

New
$540/hour
⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta
Sailing in Marina Vallarta · 16 guests

⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta

4.0
$480+/hour
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123+/day

Sailing Reviews in United States

  1. TI

    Tony

    Fairhaven/New Bedford - Sail Buzzards Bay in a Classic Sloop!

    I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

  2. DP

    Dawn

    52 Luxury Catamaran With Ac - Rates For 2 People

    ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

  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. RC

    Ryan

    Sunset Cruise in Myrtle Beach, South Carolina

    Great trip! The captain was terrific! Most of the time is spent going to and from the open ocean, but it is a scenic voyage. Fair price. Boat is in good-fair condition. We grabbed take-out at the marina before pushing off.

  5. KA

    Kaileigh

    Amazing 36' Catamaran in Puerto Aventuras, closest marina from Tulum

    They were extremely accommodating. I had accidentally booked the wrong date and Chris and team were able to re-book me for the week we were in town. The service was amazing and we are excited to return and use them again.

  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.