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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,442 Reviews)

Page 13 of 40 • 949 listings

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
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
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
40ft Private Catamaran in Riviera Maya – Up to 20 Guests
Sailing in Puerto Aventuras · 20 guests

40ft Private Catamaran in Riviera Maya – Up to 20 Guests

New
$465+/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
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
$45/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
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
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/hour
Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach
Sailing in West Palm Beach · 6 guests

Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach

5.0
$300/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
Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico
Sailing in Nuevo Vallarta · 15 guests

Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico

5.0
$160+/hour
Instant Book
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
$22/hour
Limited Availability
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
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
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
Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico
Sailing in Marina · 15 guests

Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico

5.0
$420/hour
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas
Sailing in Marina · 50 guests

Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas

4.8
$550/hour
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 35 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650/hour
38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.
Sailing in Tulum · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

5.0
Superowner
Best of 2026
$420/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,585/hour

Sailing Reviews in United States

  1. ET

    Ellan

    Captained Luxury Lagoon 560 Catamaran In The Bahamas

    Our large group of 21 with a mix of adults and kids had a great time! This was on our list for the Bahamas and it was the most epic part of our trip. We would highly recommend this company, if we are ever back, we already know who to call!

  2. SD

    Shaunak

    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

    Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!

  3. Veronica

    Veronica

    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

    My friends and I rented the catamaran boat from Jim for the 4th of July and had such an amazing time. The boat was even better in person and comfortably fit me and 12 of my friends. Captains Russell and Brian were also amazing. They were so much fun and so accommodating. They set everything up for us (the cooler with all of our drinks, bowls of chips we had brought, etc). We rented the boat for 3 hours but were having such a good time that we asked if we could pay to extend our use for another hour. Luckily they had no other immediate obligations and they were able to make it happen. As a nice bonus, they even had those fun water noodles for us to use. So much fun and my friends and I can't wait for our next boat outing with these guys!

  4. CS

    Corrie

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.

  5. ST

    Sara

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    I booked this trip as a surprise for my dear friends Rob and Leslie. This was a first anniversary trip gift. John was amazing to work with and everything went smoothly. Rob and Leslie were so excited and said it is a memory for a lifetime. I would highly recommend John and his beautiful vessel!

  6. EM

    Erin

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

    Our trip was just perfect. We were looking for a true sailing experience, and Captain Russ gave us that. My husband was at the wheel almost the entire trip, talking all things sailing Capt Russ. Meanwhile I enjoyed the sun and sounds of the water against the boat and the wind in the sails from up front. It was a peaceful and enjoyable trip, despite the wind giving out on us towards the end. We'd book with Captain Russ again in a heartbeat!