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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,363 Reviews)

Page 3 of 39923 listings

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
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
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
$134/hour
Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling
Sailing in Centro - Supmza. 001 · 15 guests

Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling

4.9
Superowner
$188/hour
High Demand
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
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
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
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
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
Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/hour
Spacious, fast 80 foot sailboat
Events in Nuevo Vallarta · 40 guests

Spacious, fast 80 foot sailboat

5.0
$275/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
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
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
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
Sail Away Private Day Trip: all inclusive with Snorkelling and Island Hop!
Sailing in San Pedro · 24 guests

Sail Away Private Day Trip: all inclusive with Snorkelling and Island Hop!

4.9
$275+/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$108/hour
Limited Availability
Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0
Superowner
Best of 2026
$150/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
$177/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
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
High End Catamaran, Luxury Private Party in Cabo San Lucas. Captain &  crew inc
Powerboats in Marina · 50 guests

High End Catamaran, Luxury Private Party in Cabo San Lucas. Captain & crew inc

5.0
Superowner
$600/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

Sailing Reviews in United States

  1. AB

    Alan

    Sail in downtown Toronto

    Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.

  2. KD

    Katherine

    Sail in downtown Toronto

    We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!

  3. 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!!!

  4. GK

    Galina

    Sail in downtown Toronto

    Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!

  5. LL

    Lucia

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Mark is the best! He was friendly and considerate, made us immediately felt comfortable once we got on the boat. Clear instructions were given, and what we did not expect was that he let all three of us learn to steer the boat : ) We learned so much on this trip and will definitely come back. If you are looking for an exciting summer boating experience plus learning something about sailing, Mark is your man!

  6. AS

    Andrew

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Thanks for a great day, Mark. We enjoyed both the your seamanship and your company. As an experienced sailor, I appreciated you creating the right combination of sailing and enjoying.