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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,474 Reviews)

Page 13 of 41 • 971 listings

41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!
Sailing in Clear Lake Shores · 6 guests

Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

5.0
$180/hour
36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers
Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers

5.0
$310/hour
Cancun Party Yacht 46ft Sea Ray Flybridge
Tours in Cancún · 15 guests

Cancun Party Yacht 46ft Sea Ray Flybridge

5.0
$200/hour
Instant Book
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

5.0
$175+/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/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
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/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
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
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
Fort Lauderdale 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips

5.0
$130+/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
$42/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
36ft Catalina Sailboat with Captain in Oceanside, California for Sunset Sails
Sailing in Oceanside · 6 guests

36ft Catalina Sailboat with Captain in Oceanside, California for Sunset Sails

New
$150/hour
37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State
Sailing in Marina del Rey · 6 guests

37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State

5.0
$200/hour
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/hour
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
Limited Availability
Beneteau Oceanis 50’ Luxury  Sailing Yacht – Chef on Board - Cartagena
Sailing in Cartagena · 12 guests

Beneteau Oceanis 50’ Luxury Sailing Yacht – Chef on Board - Cartagena

5.0
$130/hour
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/hour
We Have Your 58' Sailing Ketch. Come Join Us On Clearlake / Galveston Bay Cruise
Sailing in Kemah · 12 guests

We Have Your 58' Sailing Ketch. Come Join Us On Clearlake / Galveston Bay Cruise

New
$199/hour
Private Sailboat Beneteau 42ft in Cabo, All-Inclusive
Sailing in Marina · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0
$320/hour
Captained Luxury Lagoon 560 Catamaran In The Bahamas
Sailing in Nassau · 25 guests

Captained Luxury Lagoon 560 Catamaran In The Bahamas

5.0
$1,050/hour

Sailing Reviews in United States

  1. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!

  2. KH

    Kanisha

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    We had an amazing time with our group of 8 adults and 3 kids under 5. We had a totally customized itinerary and the crew is so incredibly helpful and welcoming. We had an amazing time on a half day charter and would definitely do a full day with this crew any time. The highlight of our trip was JoJo the dolphin following us during the whole charter! We got to snorkel with him and the kids were so happy to see him following alongside the boat the whole way!

  3. BS

    Bianca

    Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

    Captain Jim was such a personable and kind man who gave us the most beautiful afternoon on the Barefoot Babe. He taught us out to sail the boat and so much more, wish we could have stayed on for hours. It was amazing and I would definitely rent from him again if I am ever back in Houston.

  4. SC

    Sheryl

    Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

    My friened and I recently had the pleasure of embarking on a boating adventure on July 4th, and it turned out to be an unforgettable experience, all thanks to Captain Jim and his exceptional expertise. The trip took us from clear lake, Kemah Boardwalk all the way in galveston bay where we were treated to an evening of stunning sunset views, magical fireworks, and a captain who made the journey truly memorable. From the moment we stepped onto the boat, captain Jim was not only knowledgeable but also incredibly friendly and approachable, and his passion for boating and the local area shone through in every conversation. The boat itself was well-maintained, spacious, and equipped with all the necessary safety gear. Captain James took the time to ensure that everyone was comfortable and briefed us on the safety procedures, putting our minds at ease. The overall boating experience on July 4th with Captain James was amazing worth every penny. If you're seeking a knowledgeable and friendly captain, and a chance to witness mesmerizing galveston bay with affordable price, this boating experience is an absolute must!

  5. JM

    Jim

    Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

    What a great way to relax and connect with friends, family or other guests. Captain Jim will make sure that you have a wonderful day on the water. Barefoot Babe provides all of the stability your non-sailing guests might need as well as all the hands-on involvement your true sailors might want.

  6. JM

    Jim

    Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

    Highly recommended. The cruise checked off all of the boxes: friendly, timely, clean, communicative. Captain Jim was responsive to all of our requests and questions. If you want a relaxing day onboard a comfortable boat on Galveston Bay, this is the boat (ans skipper) that you should choose.