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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,509 Reviews)

Page 5 of 40 • 952 listings

Puerto Plata-private And Luxury VIP Party Yachts
Powerboats in Puerto Plata · 100 guests

Puerto Plata-private And Luxury VIP Party Yachts

3.0
Superowner
Best of 2026
$50/hour
🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.
Events in Barrio Las Yaguitas · 150 guests

🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.

5.0
$160/hour
Premium 47ft Exclusive Yacht Charter Rental Aruba
Events in Oranjestad-East · 10 guests

Premium 47ft Exclusive Yacht Charter Rental Aruba

5.0
$499/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
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$619/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
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
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
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
Hawaiian Breeze in Marina del Rey
Sailing in Marina del Rey · 6 guests

Hawaiian Breeze in Marina del Rey

5.0
$150/hour
55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!
Sailing in Marina del Rey · 12 guests

55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

4.9
Superowner
Best of 2026
$185+/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
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

4.8
$550/day
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
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
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
Limited Availability
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
$200/hour
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
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
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
$190/hour
Private 29ft Island Hopping Boat for 12 | Cartagena & Rosario Islands
Powerboats in Cartagena · 10 guests

Private 29ft Island Hopping Boat for 12 | Cartagena & Rosario Islands

4.9
$500/day
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
Premium Sunset Sailing on a True WestSail 43ft Yacht
Sailing in San Diego · 6 guests

Premium Sunset Sailing on a True WestSail 43ft Yacht

5.0
$200/hour

Sailing Reviews in United States

  1. SF

    Sarah

    55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

    We had such an amazing time out on the water, sailing a bit of the coast and then docking to jump in. Captain was communicative, professional and a total joy! The boat was spacious enough that our group of 11 could spread out in different areas. This was the final activity of a 3-day retreat and many folks named this as their top moment of the weekend! Whether you're visiting or are local and want a special way to experience the water, I highly recommend. Thanks Captain!!

  2. RM

    Robert

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

    You get the total experience when you sail with Captain Charlie and the sailboat Daffy. There is the harbor tour when leaving and returning from the ocean cruise. That is followed by an enjoyable sail off the South Florida coast--accompanied by knowledgeable commentary by Captain Charlie. He is also a most skilled sailor, as demonstrated when he outran a developing squall line to return us safe and dry to the harbor. Our group highly endorses a sailing engagement with the sailboat Daffy and Capt'n Charlie!

  3. Sebastián

    Sebastián

    Hawaiian Breeze in Marina del Rey

    Ross was awesome. We have an unforgettable experience. We thoroughly enjoyed sailing with Ross, who took care of every detail—from parking to the cleanliness and organization of the boat—and took the time to explain everything about the vessel and the sailing process. Ross also followed the agreed-upon itinerary, taking us to enjoy the beautiful views of Santa Monica and its sea lions. Highly recommended.

  4. 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!

  5. JB

    Jayne

    Premium Sunset Sailing on a True WestSail 43ft Yacht

    The most unbelievable trip with our friends for my birthday!!!! Would HIGHLY recommend for anyone!!

  6. 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!