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All listings in the United States

Awesome sailboat rentals in United States.

4.9

(8,294 Reviews)

Page 10 of 39 • 928 listings

Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0

$400/hour

Limited Availability

Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9

Superowner

$750+/hour

Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel, Mexico

5.0

$310/hour

Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New

$509/hour

Events in Marina · 10 guests

Sea Ray 350 Luxury Charter for Up to 10 Guests in Cabo, San Lucas

5.0

$230/hour

Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0

$100/hour

Limited Availability

Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0

Superowner

Best of 2026

$240+/hour

Sailing in Marina · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0

$320/hour

Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0

$110/hour

Sailing in Nassau · 26 guests

Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.

4.4

$607+/hour

Limited Availability

Sailing in San Diego · 6 guests

Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!

5.0

$450/hour

Sailing in Clear Lake Shores · 6 guests

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

5.0

$180/hour

Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0

Superowner

$117+/hour

Sailing in Marina · 50 guests

Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🎉🎶🍾⛵️

5.0

Superowner

Best of 2026

$359/hour

Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht

5.0

Superowner

Best of 2026

$17/hour

Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 20 Guests in Aruba

4.6

Superowner

$675/hour

Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

5.0

$225/hour

Tours in Cancún · 15 guests

Cancun Party Yacht 46ft Sea Ray Flybridge

5.0

$260/hour

Instant Book

Limited Availability

Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0

$187+/hour

Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7

Superowner

$145/hour

Sailing in Saint Michaels · 6 guests

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

New

$585/hour

Powerboats in Marina · 50 guests

High End Catamaran, Luxury Private Party in Cabo San Lucas. Captain & crew inc

5.0

Superowner

$600/hour

Sailing in Kilmarnock · 4 guests

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

5.0

$15+/hour

Sailing in Tamarindo · 16 guests

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

5.0

$320/hour

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Sailing Reviews in United States

MM
Mordechai

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian is an incredible host that is super passionate about his work. Every detail is thought out from the onset. He is very inviting and chilled yet extremely professional. Ian guided us through everything we would like to know about and gave many of his experienced recommendations. We had an incredible time out at sea, and are looking forward to booking our next voyage!
MA
Melis

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian is the absolute best! He took us out for an amazing trip and we had the best time ever! He knows what he’s talking about when he says “you should see new york city at night”!
Mykyta

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
This was awesome, we remember it for whole time, so smooth and beautiful
Gerard

Bali 43 Complete comfort Catamaran
Quick response. Easy booking. The actual Boat was brand new and absolutely spacious catamaran. We played music , we drank rose and swam a bit cause the water was beautiful. Captain Sebastian was the icing on the cake. Took us sailing up to Malibu and around. Good guy, professional and laid back. Already have recommended this boat to a few friends. Thanks for a great experience and day
Sandra

The nicest Charter Sailing Yacht in the West - Downtown San Francisco
We learned so much on what to do and not do on a charter. No alcohol, no plastic or black sole shoes are allowed on board. All of it made sense and was worth the sailing adventure excursion. I encourage anyone interested to go on the bay to do it, as our group had an amazing time with Captain Drew and his crew!!!
CG
Chris

The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Drew and team were top notch, they must have made a significant offering to the weather gods too because it was impeccable sailing in the bay. Great views of Alcatraz the Bay bridge Golden gate bridge was just an all around wonderful time with friends/colleagues and a great chat with the crew on a beautiful vessel.