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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,393 Reviews)

Page 13 of 39914 listings

Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/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
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0
$210+/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
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
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/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
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
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/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
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
42ft Hunter Passage Sailboat Cruising False Creek and English Bay in Vancouver
Sailing in Vancouver · 8 guests

42ft Hunter Passage Sailboat Cruising False Creek and English Bay in Vancouver

5.0
$93/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
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
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/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
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/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
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
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
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
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour

Sailing Reviews in United States

  1. AS

    Andy

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!

  2. TW

    Ted

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.

  3. Salvatore

    Salvatore

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

    Incredible sailing experience! The boat was lovely and we had a great time on the Bay.

  4. LD

    Lucy

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

    We had a beautiful day on the bay with Drew and Garrett who are both accomplished sailors and considerate hosts. Everyone felt comfortable and taken care of and I would highly recommend them to anyone looking for a day on the water with local experts. It was a gorgeous day and reminded us why we are so lucky to live here!

  5. JA

    Justin

    Curacao Private Morning Tour All Inclusive

    Thank you very much for the outstanding trip. For my families first time to Curacao this was amazing, the boat was top of the line, the food was great, the snorkeling, sailing, and views were to die for. I recommend anyone coming to the island to book some time with this boat, you will not be disappointed I promise.

  6. TH

    Toni

    Curacao Private Morning Tour All Inclusive

    My family and I had an amazing time on the Galaxie! Norbert and Hilde were amazing hosts and very knowledgeable about the water and the area. The food was delicious and the Galaxie is a gorgeous, immaculate boat. I highly recommend taking a tour with Maxie Sailing!