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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,121 Reviews)

Page 1 of 37874 listings

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
$100+/hour
Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$175/hour
Instant Book
Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$125/hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
Best of 2025
$240+/hour
Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat
Sailing in San Diego · 12 guests

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

5.0
$330/hour
Private Sailboat Beneteau 42ft in Cabo, All-Inclusive
Sailing in Juárez · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0
Best of 2025
$350/hour
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Sailing in Oxon Hill · 6 guests

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

5.0
$240/hour
Fun family time Jet Ski Rentals at Lake Norman, NC
Water Sports in Cornelius · 8 guests

Fun family time Jet Ski Rentals at Lake Norman, NC

5.0
$85/hour
Instant Book
Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta

4.6
Best of 2025
$94/hour
Instant Book
⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

5.0
Superowner
Best of 2025
$251+/hour
Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran
Sailing in Nassau · 12 guests

Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

5.0
$675/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2025
$200/hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Best of 2025
$699/hour
The Only 40ft Hinckley Sailboat in Manhattan, the Nanette Marie- Chelsea Piers!
Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan, the Nanette Marie- Chelsea Piers!

5.0
$300/hour
Instant Book
LUXURY CATAMARAN BABEL FOR ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 20 guests

LUXURY CATAMARAN BABEL FOR ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
$140+/hour
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$95/hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
Best of 2025
$600/hour
Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away
Sailing in Nuevo Vallarta · 18 guests

Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away

5.0
Superowner
Best of 2025
$263+/hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
Spacious, fast 80 foot sailboat with a hot tub
Events in Marina Vallarta · 40 guests

Spacious, fast 80 foot sailboat with a hot tub

5.0
$275/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
$450/hour
MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 40 guests

MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
Superowner
Best of 2025
$1,100/day
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
All-Inclusive Sunset Cruise in Cabo San Lucas
Tours in Marina · 45 guests

All-Inclusive Sunset Cruise in Cabo San Lucas

5.0
Best of 2025
$350/hour
Instant Book

Sailing Reviews in United States

  1. Sara

    Sara

    LUXURY CATAMARAN BABEL FOR ISLANDS, SUNSETS AND NIGHT EVENTS

    I booked the boat tour to celebrate my surprise wedding in Cartagena. It was a great experience and so much fun! The crew was so helpful and considerate. There was more than enough room for everyone. Such a highlight from our trip. Highly recommended!

  2. CD

    Camille

    Spacious, fast 80 foot sailboat with a hot tub

    Cannot recommend enough. The boat was beautiful and the staff were extremely attentive. The crew were receptive to all our requests, and gave us delicious fresh fruit and drinks as we departed onto the sea. As they were giving us a scenic cruise tour of Puerto Vallarta, we ran into a pod of humpback whales! The captain brought us SO CLOSE and we quietly snuck up around 10 feet away from the whales!!!! Experience of a lifetime, worth every dollar!!! We anchored at a gorgeous spot and they gave us fresh ceviche and guac and took us tubing! Would highly recommend the open bar add on, they had great beers and were even mixing drinks like Tequila sodas! The experience was so good, that our group was thinking of booking the same thing again for later in the week- one of the best days of my year!

  3. AE

    Anton

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    We had such an incredible day on Jonathan’s boat. The staff were super attentive and had great energy. The food was delicious and there were tons of activities on the boat. Would highly recommend and will definitely be coming again!! Thank you!

  4. CR

    Cindy

    Luxury 48' Leopard Catamaran in Cartagena

    The experience far exceeded my expectations. I booked for my 30th birthday. We had a timeeeee!! So professional. I enjoyed everything. We had the whole Catamaran to ourselves. Derek has great contacts on the spot we stoped at. You can eat on boat or get off. The water is perfect. We could do what we wanted and they were very flexible and moved with the flow. If you are considering booking with Derek , DO IT! You will not be disappointed. The whole experience was seamless. Catamaran is in great condition , size.

  5. VK

    Valentina

    LUXURY CATAMARAN BABEL FOR ISLANDS, SUNSETS AND NIGHT EVENTS

    Amory was great with all communications,helped to reschedule trip due to bad weather and was in control untill we arrived back to marina. The crew very nice,accomodating and helpful.The boat very nice ,as described.We had great time ,thank you very much.

  6. JB

    Jorge

    Luxury 48' Leopard Catamaran in Cartagena

    Derek’s Catamaran was amazing. The boat was very luxurious with plenty space to enjoy with my family and friends. You can choose to party with its great sound system and/or relax and enjoy the scenery. They give you various route options. We opted for Rosario Islands and Cholon. This was a perfect mix to party on our way there, enjoy Rosario Island beautiful waters, have lunch at Cholon and relax on our way back to Cartagena. The boat also had 4 rooms and bathrooms, perfect to take a quick shower or lay down. The staff was very friendly and helpful with serving us drinks or anything we needed. Derek was great with communication and made booking a breeze. This was the highlight of our trip. Definitely recommend it.