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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,474 Reviews)

Page 10 of 41 • 971 listings

Private Party Catamaran | Up to 12 Guests | San Diego Bay
Sailing in San Diego · 12 guests

Private Party Catamaran | Up to 12 Guests | San Diego Bay

5.0
$550+/hour
Beatiful Catalina 42' Yacht Rental in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Beatiful Catalina 42' Yacht Rental in Puerto Vallarta

5.0
Superowner
$138+/hour
Sail in Modern Luxury Beneteau Oceanis 37 Yacht
Sailing in Oceanside · 6 guests

Sail in Modern Luxury Beneteau Oceanis 37 Yacht

5.0
$200/hour
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
Limited Availability
DAYTRIP/SLEEP ON BOARD TO CATALINA
Sailing in Los Angeles · 12 guests

DAYTRIP/SLEEP ON BOARD TO CATALINA

4.9
Superowner
$199/hour
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands
Sailing in Vancouver · 6 guests

35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

5.0
$127/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/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
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

5.0
$165/hour
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/hour
50' Luxury Catamaran in Newport Beach
Sailing in Newport Beach · 12 guests

50' Luxury Catamaran in Newport Beach

New
Superowner
$700+/hour
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0
$175/hour
Set Sail on a classic 36' S2 in Chicago for up to 6 Guests
Sailing in Chicago · 6 guests

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

5.0
$200/hour
San Diego Catamaran Charter | Private Harbor Cruises or Sunset Sail - 12 guests
Sailing in San Diego · 12 guests

San Diego Catamaran Charter | Private Harbor Cruises or Sunset Sail - 12 guests

5.0
$350+/hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2026
$28/hour
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

4.7
$54/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$317/hour
50' Party Boat Catamaran in Miami  - 4 Hour Minimum - Up to 42 Guests
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami - 4 Hour Minimum - Up to 42 Guests

4.8
$1,200/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Limited Availability
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,800/day
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
50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys
Sailing in Marina · 40 guests

50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys

New
$720/hour

Sailing Reviews in United States

  1. Ashley

    Ashley

    Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

    We had an absolutely incredible time on our catamaran charter with Captain David! He truly went above and beyond to make our birthday celebration memorable. The highlight of the trip was when he sang each of us a unique, personalized happy birthday song, it was such a thoughtful and fun touch that we will never forget. If you want a captain who is professional, attentive, and knows how to make an experience truly special, book with Captain David. Highly recommended!

  2. RG

    Ryan

    Private Party Catamaran | Up to 12 Guests | San Diego Bay

    Amazing trip! First, the boat is beautiful. We had Captain Andy who was a great host. Helped us make a quick itinerary and we were on our way! Stopped for a swim before we headed back towards the harbor. I will be booking one of these trips again and would book this same one if I’m in San Diego.

  3. MD

    Michael

    Beatiful Catalina 42' Yacht Rental in Puerto Vallarta

    Muy buen servicio y comunicación. Todo el crew muy servicial. El bote fue muy lento, unas bocinas ya estaban tronadas, y no visitamos mas que 1 playa, tuvimos que pedir que nos llevaran a unos arcos cerca de la playa para ver algo mas. Había un tarp azul (perforado) que servia como sombra pero estaba nublado y con lluvia lo cual ayudo.

  4. CB

    Cassandra

    Sail in Modern Luxury Beneteau Oceanis 37 Yacht

    Brian was an amazing host! We had a great time celebrating a birthday and Brian couldn’t have been more accommodating and pleasant. His boat is immaculate and very well kept. He even let us drive the boat and taught us some things about sailing. We would highly recommend Brian!

  5. VL

    Vincent

    Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

    I booked a trip for my niece and nephew to scatter their mom's (my sister's) ashes. They were very pleased with the service, and it was a perfect day. Communication was fantastic, and the crew was very receptive to their needs. Don't hesitate to book with them!

  6. William

    William

    Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

    2nd sail w/ Rick & Deb. They are warm and entertaining hosts and their boat is a beauty. Wonderful sail last night and we were lucky to catch some wind and get up to 8 knots. A delicious charcuterie board was included. Highly recommend sailing the Artemis with Rick & Deb.