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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,339 Reviews)

Page 12 of 38912 listings

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 16 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

5.0
$320/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
Limited Availability
MAXUM 46' YACHT FOR RENT IN VANCOUVER
Events in Vancouver · 12 guests

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$357/hour
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/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
Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/hour
Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
$155+/hour
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/hour
Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran
Sailing in Chicago · 13 guests

Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

5.0
$440/hour
Limited Availability
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
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
Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.
Sailing in Isla Mujeres · 38 guests

Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.

5.0
Superowner
$262/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$107/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
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/hour
Limited Availability
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
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
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/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
Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package
Sailing in San Francisco · 10 guests

Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package

5.0
Superowner
$600+/hour

Sailing Reviews in United States

  1. Carrie

    Carrie

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

    What a Wonderful evening we had on the water with Nijole, her 1st mat (hubby) and precious little Piper "the pup". This sail boat is a MUST BOOK! Nijole's sailing abilities, great stories and knowledge of the water on and surrounding Lake Michigan are exemplar! We had such an incredible majestic peaceful evening on the water! Will be back on the HARMONY next Chicago Visit for Sure. Carrie, Kelly, Mike & Zac ( Naples, FL) :0)

  2. 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!

  3. 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.

  4. 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!

  5. MF

    Maxine

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

    Nijole was an incredible host/communicator. They made the booking and the trip easy, care-free and relaxing. The boat, The Harmony, was beautiful and clean. My fanily and I had an incredible experience and are excited to book another excursion soon!

  6. JA

    Jenny

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

    Ismael and their crew took such amazing care of me and my friends. The boat was great and service that they provided was seamless! All we had to do was enjoy the trip and they handled entering else. Everybody was also so friendly and so much fun! I would most definitely rebook with them again if I’m back in Cabo with a large group!