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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,293 Reviews)

Page 3 of 39929 listings

43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur
Sailing in Marina · 20 guests

43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur

5.0
$544+/hour
Amazing Party Boats In Puerto Plata Make Your Reservation Now
Powerboats in Puerto Plata · 100 guests

Amazing Party Boats In Puerto Plata Make Your Reservation Now

5.0
Superowner
Best of 2026
$50/hour
Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0
Superowner
Best of 2026
$150/hour
SeaRay 320 Yacht Charter in Cabo San Lucas
Events in Marina · 8 guests

SeaRay 320 Yacht Charter in Cabo San Lucas

4.9
$180/hour
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Superowner
Best of 2026
$379/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.9
$150/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/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
Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México
Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0
$265/hour
44' Leopard Catamaran All-Inclusive Charter in Riviera Maya
Sailing in Puerto Aventuras · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Riviera Maya

5.0
Superowner
Best of 2026
$520/hour
Private 38' Hunter Sailing boat in Cabo San Lucas
Sailing in Marina · 12 guests

Private 38' Hunter Sailing boat in Cabo San Lucas

4.9
Superowner
Best of 2026
$275/hour
Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
$155+/hour
Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/hour
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way
Sailing in Marina · 6 guests

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way

4.8
Superowner
$170/hour
All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas
Sailing in Marina · 50 guests

All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas

5.0
Superowner
Best of 2026
$367/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
Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 8 guests

Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico

5.0
Superowner
$119+/hour
Luxury 40' Leopard Catamaran Tours & Charters in Cartagena, Colombia
Sailing in Cartagena · 15 guests

Luxury 40' Leopard Catamaran Tours & Charters in Cartagena, Colombia

4.8
$175/hour
Instant Book
32ft Classic Sailing Charter on Swedish Sloop for 6 Guests
Sailing in Rockland · 6 guests

32ft Classic Sailing Charter on Swedish Sloop for 6 Guests

5.0
$150/hour
The Midnight Sun,  Affordable Luxury  motor yacht
Events in Oranjestad-East · 15 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0
Superowner
$498/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
Rent a 5 person Daysailer in Valle de Bravo, Mexico
Sailing in Valle de Bravo · 5 guests

Rent a 5 person Daysailer in Valle de Bravo, Mexico

5.0
$63/hour
Limited Availability
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour

Sailing Reviews in United States

  1. NN

    Natalie

    All-Inclusive Private 42’ Trimaran in Los Cabos

    My group of 19 had so much fun on this private excursion! One thing that stood out what how extremely kind and attentive the staff was. The bartender, driver, coordinator, photographer, etc. were all so nice and made sure we were safe and having fun. However a tip from me would be to not party too hard the night before because half of our group was so hungover and seasick LOL. Despite that, we still had so much fun making memories in the water. Food and drinks were great! There is a photographer on board who was very kind but there is an additional charge for photos/drone footage which we unfortunately did not purchase because it was out of budget. There are also some jelly fish in the water that some of my friends got stung by. The staff was helpful to spray some unknown liquid on the stings to prevent it from getting worse. Overall through the hangover, I still had a great time thanks to Big Mike Adventures!!!

  2. JA

    Jenny

    All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas

    Ismael and their crew took such amazing care of me and my friends. The boat was great and service that they provided was seamless! All we had to do was enjoy the trip and they handled entering else. Everybody was also so friendly and so much fun! I would most definitely rebook with them again if I’m back in Cabo with a large group!

  3. LR

    Lily

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Captain Mark was the best! The 6 of us had a great time on the sea celebrating my husband's residency graduation. There was plenty of space on the boat for all of us and we each got to take turns driving. Mark was a true pro and handled the boat with grace and ease. Would highly recommend a sail with Mark to celebrate big milestones or just to enjoy beautiful LA!

  4. AM

    Anna

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had a wonderful experience on the water with Captain Marco. He was incredibly friendly, knowledgeable, and made our family feel welcome from the moment we stepped aboard. Our children had a fantastic time, and Marco did a great job engaging with them and making the experience memorable. It was the perfect way to celebrate a special occasion as a family. Highly recommend!

  5. Francois

    Francois

    Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

    Amazing trip around the bay with Captain Jan for my daughters birthday. I was very happy with the communication pre trip which allowed me to plan properly for what we should bring and how to get to the boat, bringing me peace of mind. I also appreciated how captain Jan was flexible during the trip, including allowing us to swim in a nice cove by Angel Island. we also were lucky enough to see whales, pelicans, sea lions and porpoises. Cherry on top Jan and his partner gifted my daughters with a very cute handmade gift (I won't spill the surprise). overall great afternoon on captain Jan's boat. highly recommend for a party of 6 or less.

  6. CC

    Craig

    Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

    Jan worked with us to make this trip, exceptional. The boat is fantastic. He and his crew are fantastic. I would highly recommend booking with him. I’m a sailor and my girlfriend and I did most of the driving. Also, his boat is equipped with great electronics, which add to the experience.