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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,251 Reviews)

Page 21 of 40950 listings

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Hunter 450 Passage Yacht - Sail From Key Biscayne
Sailing in Key Biscayne · 10 guests

Hunter 450 Passage Yacht - Sail From Key Biscayne

New
Superowner
$250/hour
Sunset Blast, Open bar & Dinner
Tours in Marina · 50 guests

Sunset Blast, Open bar & Dinner

New
$2,300/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,800/hour
65ft Sailing Catamaran in Playa del Coco
Sailing in Coco · 70 guests

65ft Sailing Catamaran in Playa del Coco

5.0
$532/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
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
46ft Sailing Catamaran Private Charter / Capacity 45 people
Sailing in Cancún · 45 guests

46ft Sailing Catamaran Private Charter / Capacity 45 people

3.3
$343+/hour
🛥️🏝️ 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
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
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
$286/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
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

New
$250/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
"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
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
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
Instant Book
 Private Yacht Charters, Enjoy The Beautiful Cayman Waters in Comfort.
Events in George Town · 8 guests

Private Yacht Charters, Enjoy The Beautiful Cayman Waters in Comfort.

5.0
$375/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
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
Custom 40ft Sail Boat Rental in Cozumel
Sailing in Centro · 12 guests

Custom 40ft Sail Boat Rental in Cozumel

New
$169+/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

Sailing Reviews in United States

  1. DC

    Donte

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

  2. Cherie

    Cherie

    65ft Sailing Catamaran in Playa del Coco

    I had a great trip. Everything was a smooth process and I was able to book on a last minute whim. Jeff was very responsive and helpful throughout the booking. The staff chartering the catamaran were all amazing and I would highly recommend this company to anyone looking to get out on the water in Costa Rica.

  3. 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.

  4. 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!

  5. 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!!

  6. 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.