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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,466 Reviews)

Page 13 of 41 • 964 listings

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
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

New
Superowner
Best of 2026
$50/hour
Clean Modern Sailboat - Private Sailing Experience
Sailing in Pensacola · 6 guests

Clean Modern Sailboat - Private Sailing Experience

New
$143/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
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
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
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
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
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
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
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
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
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
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
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
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 Luxury Yacht Charter Aruba | Bilingual Crew, 4.9★ 260+ Bookings
Events in Oranjestad-East · 15 guests

Private Luxury Yacht Charter Aruba | Bilingual Crew, 4.9★ 260+ Bookings

5.0
Superowner
$530/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
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/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
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
$21/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

Sailing Reviews in United States

  1. AZ

    Adam

    Private Luxury Yacht Charter Aruba | Bilingual Crew, 4.9★ 260+ Bookings

    We had a family day on the boat with my wife and 3 kids (ages 6, 5, and 2). We had the most incredible day. Jesus and Jose catered to all of our needs especially realizing when we needed to make a slight change of plans due to some snorkeling challenges with the little ones. The food was also amazing. Consensus was that this was the best day in Aruba

  2. NH

    Nikki

    Luxury Sailing Experience on Robertson & Caine Leopard 40

    I’m so glad I decided to book this vessel! Booking was simple. The communication was accurate, timely, always professional, and with forethought, before the trip. My group was in town for a bachelorette weekend and enjoyed our day sailing with Captain Dan. We departed and returned right on time, which we appreciated as we had a schedule we were trying to adhere to. We also appreciated the blankets as it got windy at some points and we didn’t want to go inside. Overall 10/10 experience. I’d definitely book again!

  3. 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!!

  4. 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!

  5. Jen

    Jen

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

    Highly recommend booking with Captain Matthew! My out of town visitors had a really lovely time seeing the coast. It’s such a great way to enjoy the Pacific! Matthew made delicious apps for us and kept our wine topped up throughout the trip. Would definitely book again. Thank you!

  6. 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.