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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,249 Reviews)

Page 17 of 40937 listings

Private Sailing Tours in Playa Flamingo, Guanacaste
Sailing in Playa Flamingo · 17 guests

Private Sailing Tours in Playa Flamingo, Guanacaste

5.0
Superowner
$186+/hour
Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat
Sailing in Marina · 10 guests

Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

5.0
$150/hour
Private sailing tour in Cancún Mexico
Sailing in Isla Mujeres · 8 guests

Private sailing tour in Cancún Mexico

5.0
$150/hour
Blue Lagoon Catamaran 43ft Cat in Cabo San Lucas
Sailing in Marina · 20 guests

Blue Lagoon Catamaran 43ft Cat in Cabo San Lucas

New
$445/hour
COME AND ENJOY THE C'YA WITH US AND FAMILY
Events in Miami · 13 guests

COME AND ENJOY THE C'YA WITH US AND FAMILY

New
Superowner
$365+/hour
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
100' Cruising Catamaran with Unlimited Food and Drinks
Sailing in Marina · 130 guests

100' Cruising Catamaran with Unlimited Food and Drinks

5.0
$60/day
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
42' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 25 guests

42' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$363+/hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150/hour
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
Instant Book
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/hour
Lin Mar 65ft Premium Catamaran in Playas del Coco
Sailing in Coco · 45 guests

Lin Mar 65ft Premium Catamaran in Playas del Coco

New
$972+/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
Sailing in Chicago · 12 guests

No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

4.8
$245/hour
Limited Availability
LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE
Sailing in Isla Iguana · 15 guests

LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

5.0
$265/hour
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
Luxury 2021 Sailing Cat Lagoon 420
Sailing in Nuevo Vallarta · 20 guests

Luxury 2021 Sailing Cat Lagoon 420

New
$295+/hour
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat

5.0
$300/hour
Nice Sailing vessel 41ft for cruising and explore PV.
Sailing in Marina Vallarta · 12 guests

Nice Sailing vessel 41ft for cruising and explore PV.

5.0
$164/hour
55Ft Sunseeker Yacht
Powerboats in Marina · 12 guests

55Ft Sunseeker Yacht

New
$465/hour
Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0
$185/hour
Sailing Trip on 35' Catamaran in Cozumel All Inclusive
Sailing in Zona Hotelera Norte · 15 guests

Sailing Trip on 35' Catamaran in Cozumel All Inclusive

5.0
Superowner
$346/hour
5⭐️ SUNSEEKER 64’ Visit Isla Mujeres
Events in Playa del Carmen · 15 guests

5⭐️ SUNSEEKER 64’ Visit Isla Mujeres

5.0
Superowner
$749/hour

Sailing Reviews in United States

  1. JD

    Jorge

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    Captain Dennis and Kate were great hosts. Everything was perfect

  2. JS

    Jasmine

    42' Lagoon Luxury Catamaran Charter in Riviera Maya

    FIVE STARS!!! The team was amazing and definitely made the experience even in choppy waters! Christina was a very knowledgeable and awesome rockstar and was proactive in crazy situations we threw at her and the team! Definitely book with them!

  3. NB

    Nikki

    Private Sailing Tours in Playa Flamingo, Guanacaste

    The staff, the ship, the views, the food, the music…everything was awesome and was definitely the highlight of our trip to Costa Rica. Our kids even got to hold an octopus and a starfish while snorkeling! We did the full day private charter and I highly recommend it!

  4. JN

    Jennifer

    Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

    Highly recommend! Booked for a bachelorette party (8 of us), and it was definitely one of the highlights of our trip to Cabo! Reasonably priced (compared to some of the other private sails), and worth every penny! Thank you to the crew... Pepe (the Capitan) and Rooster (drinks and food) made our sail so much fun!

  5. GM

    Gabriel

    Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

    Juan, Gerardo, and Luis were absolutely great! The drinks were even better than the all-inclusive we were staying at which says a lot. We had a such a nice and relaxing time, we got to see a whale and experience some great snorkeling. I can’t recommend this experience enough!!! Perfect private Cabo sailing tour.

  6. SR

    Shannon

    Melges 24 - One Design Racing Experience

    The boat was in perfect condition, ready for anything we could ask for. Doug sails and races on a weekly basis, often in this particular boat, so his feel for the boat, the wind, and the waters we sailed in are well honed. The boat is forgiving, and Doug was unflappable. An encouraging beginner experience, and very fast under experienced guidance. I did not hope for as good an experience, and cannot offer a higher endorsement. Top marks.