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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,393 Reviews)

Page 3 of 39914 listings

Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/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
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
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
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
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
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
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
High Demand
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
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$108/hour
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
Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México
Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0
$265/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 Demand
12 passengers:  Explore San Diego Bay on a Luxury Sailing Catamaran
Sailing in San Diego · 12 guests

12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

5.0
$330/hour
Private 38' Hunter Sailing boat in Cabo San Lucas
Sailing in Marina · 12 guests

Private 38' Hunter Sailing boat in Cabo San Lucas

4.9
Superowner
Best of 2026
$275/hour
All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas
Sailing in Marina · 50 guests

All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas

5.0
Superowner
Best of 2026
$367/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
High Demand
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
Schock 35' Cruiser Sailboat in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35' Cruiser Sailboat in San Francisco Bay

5.0
$99/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$631/hour
Luxury Tripp 43 Sailboat Charter in San Francisco Bay
Sailing in Alameda · 12 guests

Luxury Tripp 43 Sailboat Charter in San Francisco Bay

5.0
$189/hour
Beautiful Classic Sailboat in Marina Del Rey
Sailing in Marina del Rey · 10 guests

Beautiful Classic Sailboat in Marina Del Rey

5.0
$170+/hour
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way
Sailing in Marina · 6 guests

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way

4.8
Superowner
$170/hour
Luxury Leopard 38 Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Leopard 38 Catamaran located in Downtown Miami

5.0
$219+/hour

Sailing Reviews in United States

  1. 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!

  2. 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!!!

  3. MH

    Michaella

    Luxury Tripp 43 Sailboat Charter in San Francisco Bay

    Dan was amazing! I couldn’t have asked for a better experience for my birthday. He gave us lots of options on routes to take and was very knowledgeable. I felt very safe on board with him and would recommend him to anyone!

  4. Kim

    Kim

    Sail in downtown Toronto

    Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!

  5. CP

    Colleen

    Sail in downtown Toronto

    We had a fabulous afternoon sailing with Captain Dom. He was very welcoming, friendly and knowledgeable. We immediately felt safe and comfortable sailing with him. The boat was clean and very comfortable and the vibe was relaxing and chill. We enjoyed being out on the lake with the great views of the skyline. It’s a great way to unwind and spend some quality time with some family or friends. I would definitely recommend this experience and I will be booking again to sail with Captain Dom.

  6. EC

    Ehsan

    Sail in downtown Toronto

    We had a great night with Dom. He was very friendly, kind, and easy to talk to, and made the whole experience enjoyable from start to finish. He also took so many great photos of us, and we’ll always have those memories. We had an amazing time and would definitely recommend this tour to anyone. Thanks again, Dom!