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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,393 Reviews)

Page 13 of 39915 listings

Shared Catamaran Sailing Tour To Passion Island (9am to 2pm)
Sailing in Zona Hotelera Norte · 35 guests

Shared Catamaran Sailing Tour To Passion Island (9am to 2pm)

5.0
$23/hour
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht

5.0
Superowner
Best of 2026
$17/hour
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
High Demand
42ft Hunter Passage Sailboat Cruising False Creek and English Bay in Vancouver
Sailing in Vancouver · 8 guests

42ft Hunter Passage Sailboat Cruising False Creek and English Bay in Vancouver

5.0
$93/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas
Sailing in Marina · 50 guests

Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas

4.8
$550/hour
Enjoy a small group Shared Sunset Sailing Cruise in Cabo San Lucas
Sailing in Marina · 14 guests

Enjoy a small group Shared Sunset Sailing Cruise in Cabo San Lucas

5.0
Superowner
Best of 2026
$60/hour
Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico
Sailing in Marina · 15 guests

Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico

5.0
$420/hour
38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.
Sailing in Tulum · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

5.0
Superowner
Best of 2026
$420/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay
Sailing in Kemah · 12 guests

46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay

5.0
$512+/hour
High Demand
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
Curacao Private Sunset Tour Deluxe
Sailing in Jan Thiel · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way
Tours in Cancún · 15 guests

Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way

5.0
$210/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

5.0
$195/hour
50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle
Sailing in Seattle · 47 guests

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

4.9
$1,050/hour
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 10 guests

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$32/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

5.0
Superowner
$650+/hour

Sailing Reviews in United States

  1. LM

    Liz

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  2. LF

    Lena

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

    Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

  3. TB

    Tom

    50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

    I rented this boat for my 40th birthday party with around 40 adults during Sea Fair and it was a great experience.

  4. Mv

    Marcos

    Shared Catamaran Sailing Tour To Passion Island (9am to 2pm)

    The crew on the Belle d’ Alice Catamaran are incredibly accommodating and genuinely nice and made our experience much more memorable. Lunch was authentically delicious and perfect after our time at Isla Pasion. The catamaran was very clean and well kept. We will definitely book again!

  5. CS

    Corrie

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.

  6. ST

    Sara

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    I booked this trip as a surprise for my dear friends Rob and Leslie. This was a first anniversary trip gift. John was amazing to work with and everything went smoothly. Rob and Leslie were so excited and said it is a memory for a lifetime. I would highly recommend John and his beautiful vessel!