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All listings in the United States

Awesome sailboat rentals in United States.

4.9

(8,205 Reviews)

Page 4 of 40 • 945 listings

Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8

Superowner

Best of 2025

$800/hour

Instant Book

Events in Oranjestad-East · 15 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0

Superowner

Best of 2025

$450/hour

Instant Book

Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0

$165/hour

Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0

Superowner

$150/hour

Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0

$136/hour

Sailing in San Diego · 6 guests

Pure Sport Catamaran Sailing on San Diego Bay

5.0

$220/hour

Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.8

$150/hour

Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0

$129+/hour

Events in Marina · 8 guests

SeaRay 320 Yacht Charter in Cabo San Lucas

4.9

$180/hour

Instant Book

Sailing in Marina del Rey · 8 guests

Beautiful Jeanneau 58' Sailboat in Marina del Rey

4.8

$400/hour

Sailing in Marina · 30 guests

Big Luxury Catamaran 52 Lagoon Bar Sunset Food Music Snorkelng 4 Rooms Bathrooms

5.0

$450/hour

Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0

Superowner

Best of 2025

$800/hour

Instant Book

Sailing in Cancún · 23 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0

$434/hour

Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0

$265/hour

Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0

$205+/hour

Sailing in Marina del Rey · 12 guests

Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!

5.0

$208+/hour

Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0

$175+/hour

Sailing in Marina del Rey · 12 guests

55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.

5.0

Best of 2025

$185+/hour

Sailing in Juárez · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0

Best of 2025

$350/hour

Sailing in Alameda · 6 guests

Schock 35 Cruiser Racer in San Francisco Bay

5.0

$134/hour

Events in Cancún · 8 guests

Luxury 42ft Sea Ray Motor Yacht Charter for up to 8 people in Cancun

5.0

$136/hour

Instant Book

Sailing in Mount Pleasant · 6 guests

40 ft Luxury Catamaran Sailing Yacht in Charleston

5.0

Superowner

$300/hour

Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0

$75/hour

Events in Puerto Aventuras · 12 guests

40' Sea Ray Sundancer All-Inclusive Yacht Charter in Riviera Maya.

5.0

Superowner

$350/hour

Top Destinations Nearby

Sailing Reviews in United States

RL
Rachel

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Mark was great! He responded quickly and answered all my questions. My friends and I came for a bachelorette party and had the best time! Definitely recommend Mark, we had an awesome time on the beautiful boat.
Brittany

Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰
SE
Sara

55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.
We had such a fun time sailing with Captain Stephen! The boat was perfect for our group of eleven and it was so nice getting out on the water. Easy to book and communicative with all our questions — highly recommend if you’re looking for a fun day with friends!
Brad

Cal 36 Sailboat Rental in Marblehead, Massachusetts
We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!
Van A.

Charter this beautiful Catalina from Milwaukee, WI - Captain Included
A great Milwaukee skyline sail with an old sailor and his 8 and 5 year old grandkids. Patrick was totally accommodating and I was very happy. Toby “loved the ride” And Betty feigned boredom. I know they both loved the experience. Patrick our skipper was great. The boat clean and well cared for.
GP
George

Cal 36 Sailboat Rental in Marblehead, Massachusetts
Had a great time with Captain Allan, truly a fun time and he was very concerned about us enjoying the experience. We highly recommend him and his service. You won’t be disappointed!