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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,449 Reviews)

Page 3 of 39930 listings

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

5.0
$250/hour
La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California
Sailing in Oceanside · 6 guests

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

5.0
$150/hour
Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9
Superowner
$700+/hour
Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo
Sailing in Tamarindo · 20 guests

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,190/day
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
Sailing in Cartagena · 16 guests

Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

4.8
Superowner
$870/day
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2026
$220/hour
43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur
Sailing in Marina · 20 guests

43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur

5.0
$544+/hour
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

4.7
$132/hour
Spacious, fast 80 foot sailboat
Events in Nuevo Vallarta · 40 guests

Spacious, fast 80 foot sailboat

5.0
$275/hour
Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests
Sailing in Cancún · 30 guests

Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests

New
Superowner
$300/hour
30ft Sailing Yatch. Real & Unique Sailing in Mazatlán
Sailing in Marina Mazatlán · 8 guests

30ft Sailing Yatch. Real & Unique Sailing in Mazatlán

5.0
$2,000/hour
38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.
Sailing in Puerto Aventuras · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.

5.0
Superowner
Best of 2026
$420/hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Superowner
$325/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.9
$150/hour
Luxury Catamaran Leopard 48 in Santa Marta Colombia
Sailing in Santa Marta · 10 guests

Luxury Catamaran Leopard 48 in Santa Marta Colombia

5.0
$150/hour
48ft Maui Catamaran for Island, Sunsets and Night Events
Sailing in Cartagena · 40 guests

48ft Maui Catamaran for Island, Sunsets and Night Events

5.0
Superowner
$999/day
Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!
Sailing in Marina · 70 guests

Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

5.0
$352/hour
Instant Book
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Superowner
Best of 2026
$379/hour
Private 44ft Trimaran in Los Cabos for 50 Guests
Sailing in Juárez · 50 guests

Private 44ft Trimaran in Los Cabos for 50 Guests

5.0
Superowner
Best of 2026
$250/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat
Sailing in Newport · 6 guests

Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat

5.0
$400/hour
Limited Availability
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo
Sailing in Valle de Bravo · 16 guests

Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo

5.0
$174/hour

Sailing Reviews in United States

  1. Jen

    Jen

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan again.

  2. SP

    Sawkia

    48ft Maui Catamaran for Island, Sunsets and Night Events

    The staff tending to us on the boat was awesome and the communication leading up to the boat was great! The communication about the itinerary could have been better! All in all great day despite the mix up. Thank you and will book again!

  3. AW

    Ariana

    Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

    My group of 13 and I had an excellent time aboard! From the moment we got on the boat, the vibes were great! I chose this boat because it offered lunch in addition to an open bar. The food was good and the drinks were strong! I couldn't have asked for a better bachelorette party experience!

  4. Barb

    Barb

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!

  5. fd

    frank

    Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

    We had a wonderful experience sailing to the Rosario islands! Nicholas was such a kind person, easy to communicate with and organized our trip well taking care of everything. Tatiana was so kind as well. She met us at the dock and got us on board with ease. The boat was well maintained and had everything we wanted for a great day. The crew was outstanding! The captain took us to all of the areas we asked for. We wanted to stay away from the tourist areas and he knew just where to take us. His crew member took great care of everything, serving us drinks and food as well as helping us throughout the trip! We rent boats a few times a year and this experience is one of the best we have had. We highly recommend!!!

  6. Doug

    Doug

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik did a great job getting us out on the water. There was a storm coming in and we had to cut the sail a little short but the winds did not disappoint. Great tour of the harbor and the city skyline. Patrik let us take the helm and experience sailing on the lake. Wish we had more time but better to be safe and dry.