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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,496 Reviews)

Page 14 of 40 • 951 listings

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

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico
Sailing in Marina · 15 guests

Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico

5.0
$420/hour
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas
Sailing in Marina · 50 guests

Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas

4.8
$550/hour
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 35 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650/hour
38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.
Sailing in Tulum · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

5.0
Superowner
Best of 2026
$420/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,585/hour
49-Passenger Sailing Charter Catamaran at Navy Pier Marina
Sailing in Chicago · 49 guests

49-Passenger Sailing Charter Catamaran at Navy Pier Marina

New
$900/hour
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,700/day
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 12 guests

Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$280/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay
Sailing in Kemah · 12 guests

46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay

5.0
$512+/hour
50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle
Sailing in Seattle · 47 guests

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

4.9
$1,050/hour
Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/hour
Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way
Tours in Cancún · 15 guests

Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way

5.0
$210/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

5.0
$195/hour
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building
Sailing in Vancouver · 8 guests

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

5.0
$175/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour

Sailing Reviews in United States

  1. KB

    Katya

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    We had a great trip with Paul! He was super communicative and easy to plan with

  2. 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!

  3. Tiffany

    Tiffany

    Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico

    This private boat party was the highlight of my trip. The hostess Zaria and her crew were so amazing. The food and drinks were great especially the guacamole! I loved that the pole provided more laughs and fun. Pictures were taken during the entire ride and you receive a link with all pictures. If you’re looking for a party boat full of fun this is definitely the boat you want!

  4. PC

    Peter

    Sailing Hobie Cat Rental in Noord, Aruba

    Lisa was a great host as she welcomed us and got us squared away with the 16 ft Hobie Cat w/jib! The whole experience was incredible and we got some great speed on the Hobie Cat. It was a high wind day (25-30 mph) and we couldn’t have asked for a better time on the water. Lisa was gracious, helpful, and fun!

  5. NS

    Nirali

    Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas

    I recently organized a trip to Cabo with 42 friends, where we rented a boat with a Captain. Our experience was fantastic! They accommodated our vegetarian dietary preferences with a variety of options and provided unlimited drinks. The staff were incredibly friendly, and the quality of the professional photos they offered was exceptional. The Captain was prompt in responding to messages and extremely courteous throughout. The entire process went seamlessly, and I highly recommend this boat rental service!

  6. PJ

    Preslee

    Stunning 60ft Party Catamaran for Exclusive Parties in Cabo San Lucas

    We went on an unforgettable journey with the friendliest crew in Cabo! From the moment we stepped aboard, the atmosphere was perfect, the food was delicious, and the drinks that were included were so good as well. Carlos and his team made sure everyone was having a great time, and their communication was so quick and easily responsive to all the questions we had before the trip. We were able to relax, and party with friends, and this boat trip was a can't-miss experience in Cabo! Thank you so much to Carlos and crew for giving us a unforgettable time!