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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,449 Reviews)

Page 5 of 39930 listings

Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events
Sailing in Cancún · 40 guests

Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events

5.0
Superowner
$300/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$628/hour
2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 17 guests

2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico

5.0
$370+/hour
Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

5.0
$200/hour
Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!
Sailing in Marina Vallarta · 12 guests

Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!

5.0
Superowner
$145/hour
See the wonders of Puerto Vallarta aboard 38' Sailing Catamaran Charter
Sailing in Isla Iguana · 12 guests

See the wonders of Puerto Vallarta aboard 38' Sailing Catamaran Charter

5.0
Superowner
Best of 2026
$240/hour
Luxury 50ft Custom Catamaran in Vancouver for 12 Guests
Sailing in Vancouver · 12 guests

Luxury 50ft Custom Catamaran in Vancouver for 12 Guests

5.0
$393/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$450/hour
Come sail away on this Jeanneau 58' Sailboat in San Diego
Sailing in San Diego · 6 guests

Come sail away on this Jeanneau 58' Sailboat in San Diego

4.8
$400/hour
Yacht Party 42' Sea RaySundancer Free 1-way pick up transportation Hotel Marina
Events in Cancún · 8 guests

Yacht Party 42' Sea RaySundancer Free 1-way pick up transportation Hotel Marina

5.0
$180/hour
Instant Book
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$240/hour
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

4.8
$550/day
Premium 47ft Exclusive Yacht Charter Rental Aruba
Events in Oranjestad-East · 10 guests

Premium 47ft Exclusive Yacht Charter Rental Aruba

5.0
$499/hour
Unforgettable Adventure Aboard a 75’ Sailing Schooner Charter in Long Beach
Sailing in Long Beach · 12 guests

Unforgettable Adventure Aboard a 75’ Sailing Schooner Charter in Long Beach

5.0
Superowner
$189+/hour
Instant Book
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
$190/hour
Luxury 42ft Catamaran Sailing Charter in Charleston Harbor
Sailing in Mount Pleasant · 6 guests

Luxury 42ft Catamaran Sailing Charter in Charleston Harbor

5.0
Superowner
$235+/hour
Morgan 382 Sailboat for charter in Pensacola, Florida
Sailing in Pensacola · 6 guests

Morgan 382 Sailboat for charter in Pensacola, Florida

5.0
$75/hour
13 person Sailing Yacht Chicago Weekday Special 4th Hour Free!
Sailing in Chicago · 13 guests

13 person Sailing Yacht Chicago Weekday Special 4th Hour Free!

5.0
$550/hour
$650hr | 12 Guests | SLX400
Events in Washington · 13 guests

$650hr | 12 Guests | SLX400

4.5
Superowner
$700/hour
Instant Book
Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia
Sailing in Cartagena · 20 guests

Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia

4.8
Superowner
$900/day
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/hour
Charter Open Bar Catamaran for a Boat Party in Cancún and Isla Mujeres
Sailing in Cancún · 40 guests

Charter Open Bar Catamaran for a Boat Party in Cancún and Isla Mujeres

5.0
$290+/hour
Hawaiian Breeze in Marina del Rey
Sailing in Marina del Rey · 6 guests

Hawaiian Breeze in Marina del Rey

5.0
$150/hour
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Sailing in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour

Sailing Reviews in United States

  1. MB

    Maria

    Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

    I am new to the world of sailing, and this was an awesome experience. I was able to have hands-on learning about sailing in the midst of a safe environment and a competent captain. As I don’t own, my own boat, the cost was very reasonable. I plan to do this again then near future!

  2. LS

    Lisette

    Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia

    Highly Recommended Catamaran Cruise in Cartagena! We had an absolutely wonderful time on our catamaran cruise in Cartagena with a group of 10, and every single person loved it from start to finish. The boat was comfortable, the crew was friendly and attentive, and the entire experience felt perfectly organized and relaxing. The highlight for me was the delicious fried fish served onboard, fresh, flavorful, and a real treat, while the swim stops were fantastic, with clear water, fun locations, and a very safe setup that made everyone feel comfortable jumping in. It was the ideal mix of scenic sailing, refreshing swims, and good vibes. We’ll definitely be booking this again the next time we’re in Cartagena!

  3. JK

    Jason

    See the wonders of Puerto Vallarta aboard 38' Sailing Catamaran Charter

    Perfect day on the water. Had a great day playing it by ear in Banderas Bay. The boat was top-notch and the crew was excellent at taking care of us. Really was an awesome time. I definitely recommend!

  4. Susan

    Susan

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    This was a perfect sailing experience. The boat is immaculate, comfortable and beautiful. Captain Joe is incredibly knowledgable and fun! Everyone should get a chancw to experience this!!!!

  5. AG

    Allison

    The Wanderlust Ultimate Catamaran Adventure

    We cannot say enough wonderful things about our charter! It was truly one of the best experiences we’ve had as a family. Captain David was fantastic—knowledgeable, easygoing, and absolutely wonderful with our kids. He took us on an amazing snorkeling adventure and made the experience so easy and fun for them. Ashley was the sweetest with our daughter and made us a delicious lunch, and Max completely made Jack’s day by letting him help around the boat. The whole crew was warm, fun, and incredibly accommodating. We made such special family memories and will absolutely be rebooking on our next trip. Couldn’t recommend them more!

  6. SP

    Samir

    Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events

    Joe was an amazing host. Everything was just as described and he met everyone’s expectation. They went above and beyond to make sure we were accommodated. I would highly recommend