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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,249 Reviews)

Page 9 of 40950 listings

65' Custom Trimaran with Waterslides [All Inclusive] in Puerto Vallarta Mexico
Powerboats in Área Militar de Vallarta · 85 guests

65' Custom Trimaran with Waterslides [All Inclusive] in Puerto Vallarta Mexico

4.3
Superowner
Best of 2025
$815/hour
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Instant Book
Private Yacht SeaRay 46ft Cancun, Quintana Roo
Tours in Cancún · 15 guests

Private Yacht SeaRay 46ft Cancun, Quintana Roo

5.0
$174/hour
Instant Book
36ft Sailing Catamaran Charter for Up to 20 People in Cancún
Sailing in Cancún · 20 guests

36ft Sailing Catamaran Charter for Up to 20 People in Cancún

New
$129+/hour
Instant Book
Private Harbor Cruise in Newport Beach, California
Tours in Newport Beach · 4 guests

Private Harbor Cruise in Newport Beach, California

5.0
$200/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
$300+/hour
Instant Book
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
Your own 42' private Sailboat in Cabo
Sailing in Marina · 14 guests

Your own 42' private Sailboat in Cabo

5.0
Superowner
$264/hour
Instant Book
3-hour exclusive Catamaran Sunrise or Sunset
Sailing in Isla Mujeres · 16 guests

3-hour exclusive Catamaran Sunrise or Sunset

4.9
Superowner
Best of 2025
$262/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!

5.0
$175+/hour
NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA
Sailing in Los Angeles · 12 guests

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA

5.0
Superowner
$169+/hour
37ft Sea Ray Sundancer Yacht for Charter  in Cabo San Lucas, Baja California Sur
Events in Marina · 8 guests

37ft Sea Ray Sundancer Yacht for Charter in Cabo San Lucas, Baja California Sur

5.0
$230/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
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
Best of 2025
$1,000/day
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
Best of 2025
$960/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$295/hour
Luxury Lagoon 440 Sailing Catamaran in Key West
Sailing in Key West · 6 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0
$250/hour
Trireme 43 Sailing Trimaran 24M in Vibrant Mazatlan
Sailing in Marina Mazatlán · 25 guests

Trireme 43 Sailing Trimaran 24M in Vibrant Mazatlan

5.0
$127/hour

Sailing Reviews in United States

  1. PH

    Paige

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    Had a great day out on Matthew’s lovely sunfish. Matt was very communicative and also offered us an alternative activity in case of no wind. Thankfully, the wind filled and my mom and I had a great day of sailing on beautiful MerryMeeting Lake! Matt was very pleasant to talk with and answered all of our questions about the area and the boat. We will definitely be back and would encourage others to rent this boat from Matt!

  2. LF

    Liz

    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

    Wonderful experience! My family and friends had an amazing time. Captain Eric was great. If you check out Trip Advisor and Google, you'll see all his other great reviews.

  3. ST

    Stephen

    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

    Great boat with a knowledgeable captain/owner.

  4. AP

    Albalia

    Morgan 382 Sailboat for charter in Pensacola, Florida

    We shared our 24th wedding anniversary with Robert and Carly in their beautiful boat. The only thing we regret is not doing this sooner because they are amazing and it is an experience to cherish. You guys are the best and we will definitely be back! Looking forward for that paella next time! Thank you!!!

  5. Dominic

    Dominic

    65' Custom Trimaran with Waterslides [All Inclusive] in Puerto Vallarta Mexico

    HIGHLY RECOMMEND!! The boat and crew are amazing. We had a party of 25 with 9 kids aging from 4-15 and the staff was attentive and amazing with all of them. Plenty to eat and drink so get the fajitas option if you book. The only regret is we didn’t book a longer trip. Thanks again to the amazing staff for a fun day!

  6. SH

    Scott

    65' Custom Trimaran with Waterslides [All Inclusive] in Puerto Vallarta Mexico

    We had a great time. The crew took care of our group of 34. Some folks relaxed while others took part in the water activities, water slides, and diving off the boat. We chose the lunch option and the food was great; and there was more than plenty for the group. You want a fun day on the bay? Book this boat.