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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,249 Reviews)

Page 11 of 40950 listings

Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.5
Superowner
$125+/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
Marlowe Hunter 33’ Sailing in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing in Fort Lauderdale

5.0
$90+/hour
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

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

4.9
$750+/hour
Instant Book
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2025
$50/hour
Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.
Sailing in Nassau · 26 guests

Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.

4.4
$607+/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

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

5.0
$100/hour
Leopard 51 with flybridge in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 with flybridge in Tulúm

5.0
Superowner
$626/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$300/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
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/hour
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Sailing in Nassau · 12 guests

Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.

4.7
$252+/hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225/hour
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$269/hour
Beneteau Modern Premium Sailboat from San Francisco
Sailing in San Francisco · 6 guests

Beneteau Modern Premium Sailboat from San Francisco

5.0
$220+/hour
Instant Book
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
Sailing Sloop Hunter 40 in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7
Superowner
Best of 2025
$130/hour
 Chica Sailing Adventure 41' Sailboat [All Inclusive] in Puerto Vallarta Mexico
Sailing in Nuevo Vallarta · 16 guests

Chica Sailing Adventure 41' Sailboat [All Inclusive] in Puerto Vallarta Mexico

5.0
Superowner
Best of 2025
$414/hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
Best of 2025
$800/hour
Instant Book

Sailing Reviews in United States

  1. CW

    Carly

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    I rented the boat for and engagement photo shoot. The weather this time of year was very unpredictable and rainy, but Captain Gerald was great to work with and so funny. He made the day really enjoyable. Lovely boat and nice time, highly recommend!

  2. Evan

    Evan

    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Captain Paul and his wife, Melissa, were absolutely wonderful. I spent my birthday on their gorgeous sailboat with a group of friends, and we had the best day! The boat itself was stunning and Paul and Melissa went above and beyond to make our day perfect.

  3. KP

    Kendra

    Hunter 43 Sailing Yacht in Oakville, Ontario

    We had a great time on Dave’s boat! He recommended a beach area where we could anchor and swim around and let the kids get involved with the sailing when they asked. Very friendly and the boat was exactly what we expected.

  4. FC

    Fionnella

    Hunter 43 Sailing Yacht in Oakville, Ontario

    Great experience. Competent captain who is flexible with the itinerary. Enjoyed our 3 hour sail.

  5. NR

    Natalie

    Pirate Ship in Avalon, Catalina

    A true Pirate Adventure! 🏴‍☠️ This was the trip of a lifetime to Catalina Island, felt like a movie the whole time because it was so beautiful. We saw pods of dolphins, got to sleep on the ship anchored just off shore, and were spoiled with the coolest private shore boat to the island whenever we wanted to explore! Captain Andrew is a great host, captain, and history buff. We so enjoyed his cool answers to our questions about everything we could see on the ship, on the way, and on the island! We also felt extremely safe the whole time trip. I highly recommend booking with him. This would be a dream birthday pirate adventure, photo shoot or music video set location, unique romantic getaway, staycation for something unique in LA that your friends will be jealous of! There are fun props like swords and hats, and we even got to shoot the real cannon!

  6. JP

    John

    Let's Go Sail in Gloucester Point, Virginia

    Captain Bill was a fantastic host for our inaugural sailing adventure in the York River out of Gloucester Point, VA. We booked him for a Saturday afternoon in June for a 2:30 to 5:30 cruise and it was everything we could have asked for and more. He explained the region's waters and relation to the Chesapeake Bay as well as the naval and nautical history of the area in addition to teaching us about his boat and how to sail it properly. We wanted to be immersed in the experience and he let us be very hands on, giving direction for assisting with deploying the sails, commanding the helm, reading the wind and performing the tacking maneuvers while being at the helm. We also had a chance to relax on the forward section of the deck as Bill took over, he passed our libations to us and helped us enjoy the experience of sailing while soft music played that even invited an interaction with one of the regions local dolphin who accompanied and entertained us for well over a half an hour on our return up the river. What an awesome way to spend an afternoon.