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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,479 Reviews)

Page 18 of 41 • 973 listings

Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”
Sailing in Chicago · 10 guests

Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

5.0
$275/hour
Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat
Sailing in Marina · 10 guests

Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

5.0
$150/hour
Private sailing tour in Cancún Mexico
Sailing in Isla Mujeres · 8 guests

Private sailing tour in Cancún Mexico

5.0
$150/hour
Private 40ft Lagoon Sailing Catamaran in Cartagena
Sailing in Cartagena · 18 guests

Private 40ft Lagoon Sailing Catamaran in Cartagena

New
$325/hour
Luxury 44ft Lagoon Catamaran Charter in Rosario Islands
Sailing in Cartagena · 23 guests

Luxury 44ft Lagoon Catamaran Charter in Rosario Islands

New
$350/hour
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Sailing in North Vancouver · 10 guests

Charter Jeanneau 50 DS Sailing Yacht in English Bay

5.0
$352/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/hour
Private 2.5 Hour Glass-Bottom Boat Tour with Cabo Arch & Snorkeling
Powerboats in Marina · 12 guests

Private 2.5 Hour Glass-Bottom Boat Tour with Cabo Arch & Snorkeling

New
$150/hour
23' Ranger Daysailer in Oakland, California
Sailing in Oakland · 5 guests

23' Ranger Daysailer in Oakland, California

5.0
$70/hour
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123+/day
Private Catamaran Negril – Rick's Café Sunset & Open Bar
Sailing in West End · 60 guests

Private Catamaran Negril – Rick's Café Sunset & Open Bar

New
$2,740/day
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained

5.0
$300/hour
Beautiful & Luxury 44 Lagoon New Catamaran in Cozumel / Private Tour in Cozumel
Sailing in San Miguel de Cozumel · 30 guests

Beautiful & Luxury 44 Lagoon New Catamaran in Cozumel / Private Tour in Cozumel

5.0
$494/hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,600/hour
Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2
Sailing in Marina del Rey · 6 guests

Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2

New
$150/hour
Sailing Trip on 35' Catamaran in Cozumel All Inclusive
Sailing in Zona Hotelera Norte · 15 guests

Sailing Trip on 35' Catamaran in Cozumel All Inclusive

5.0
Superowner
$322/hour
San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat
Sailing in San Diego · 8 guests

San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat

5.0
$300/hour
Private Catamaran Charter to Passion Island, Cozumel | 44ft Voyage Yacht
Sailing in Zona Hotelera Norte · 20 guests

Private Catamaran Charter to Passion Island, Cozumel | 44ft Voyage Yacht

5.0
$376/hour
Luxury Private Sail Yacht rental for groups and families up to 15 Pax
Sailing in Isla Mujeres · 15 guests

Luxury Private Sail Yacht rental for groups and families up to 15 Pax

5.0
$129/hour
5⭐️ SUNSEEKER 64’ Visit Isla Mujeres
Events in Playa del Carmen · 15 guests

5⭐️ SUNSEEKER 64’ Visit Isla Mujeres

5.0
Superowner
$698/hour
40ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
Private Cat 30' Magic-Sea-wind Sailing Catamaran
Sailing in Cancún · 20 guests

Private Cat 30' Magic-Sea-wind Sailing Catamaran

5.0
$165+/hour
Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del Carmen
Sailing in Centro - Supmza. 001 · 16 guests

Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del Carmen

5.0
$200+/hour

Sailing Reviews in United States

  1. JN

    Jennifer

    Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

    Highly recommend! Booked for a bachelorette party (8 of us), and it was definitely one of the highlights of our trip to Cabo! Reasonably priced (compared to some of the other private sails), and worth every penny! Thank you to the crew... Pepe (the Capitan) and Rooster (drinks and food) made our sail so much fun!

  2. GM

    Gabriel

    Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

    Juan, Gerardo, and Luis were absolutely great! The drinks were even better than the all-inclusive we were staying at which says a lot. We had a such a nice and relaxing time, we got to see a whale and experience some great snorkeling. I can’t recommend this experience enough!!! Perfect private Cabo sailing tour.

  3. HS

    Harman

    Charter Jeanneau 50 DS Sailing Yacht in English Bay

    Chris and his wife were amazing. I Did a surprise proposal. They were so professional they greeted us outside the boat with uniforms. Both of them helped my whole family get on board safely. He Gave us all the guidelines to be safe. Really cared for our safety. We were around some crazy boaters that night and they had no clue what they were doing and Chris jumped into action saved us every time, he’s well prepared for anything that might happen. He’s a very trust worthy captain his background shows for it. His sail boat is amazing it’s huge and it’s spacious and clean. It’s really nice and well maintained. I would definitely rent again. Price is amazing for what you get and him and his wife have such a great personality. They also helped us off load and take stuff back to our cars amazing people. Highly recommend renting from him. Safest captain

  4. MR

    Matt

    Charter Jeanneau 50 DS Sailing Yacht in English Bay

    Chris and Michelle were fantastic hosts aboard their boat. We had a group of nine, including a baby and it was the perfect way to spend an afternoon in Vancouver. We got to see incredible views of the city during a peaceful sail and enjoyed the company that Chris, Michelle and Frederick (the cat) provided. Strongly recommend and would book with them again.

  5. ST

    Samantha

    Custom Sailing Charter - Newport/ Block Island

    We really enjoyed our sail with Candace, Stephanie and Matt - and we can't forget Eddie Spaghetti the daschaund! They told us a lot about the history of the area and made sure we were comfortable and well-taken care of on this sail. Many thanks to Stephanie too for the wonderful photos on the trip.

  6. sk

    sarah

    Custom Sailing Charter - Newport/ Block Island

    Captain Candace, Captain Don and Stephanie were an absolute delight to work with from start to finish. Capt. Candace was very easy to communicate with and worked to accommodate our age diverse group. Great directions and instructions as to how to find the boat, the boat was in pristine condition and VERY comfortable accommodations for our sail. Captain Don and Stephanie were very clear about safety first at all times, very knowledgable sailers and wonderful tour guides and historians when the wind was not working with us. We could not have asked for anything more - the boat and the crew are top notch. We hope to have the opportunity to sail with Candace and crew again. Our sailing experience was the highlight of our trip to Newport.