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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,496 Reviews)

Page 28 of 40 • 951 listings

Sail Boat for a Classy sailing adventure.
Sailing in Marina Vallarta · 10 guests

Sail Boat for a Classy sailing adventure.

New
$130/hour
All Inclusive Lagoon 42' Sailing Catamaran In Playa Del Carmen
Sailing in Playa del Carmen · 25 guests

All Inclusive Lagoon 42' Sailing Catamaran In Playa Del Carmen

New
Superowner
$450+/hour
Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish
Sailing in Negril · 100 guests

Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

New
$1,800/hour
⛵️  MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
Events in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

New
Superowner
$750+/hour
38ft Lagoon Catamaran Sailing Lessons in Chicago
Tours in Chicago · 6 guests

38ft Lagoon Catamaran Sailing Lessons in Chicago

New
$350+/hour
Amazing Day on 43' Sailing Catamaran with Unlimited Open Bar
Sailing in Cancún · 35 guests

Amazing Day on 43' Sailing Catamaran with Unlimited Open Bar

New
$285/hour
Sunset cruise on a luxury catamaran up to 20 guests
Sailing in Nassau · 20 guests

Sunset cruise on a luxury catamaran up to 20 guests

New
$933/hour
Lagoon 440 Catamaran rental in Cancun Isla Mujeres
Sailing in Cancún · 25 guests

Lagoon 440 Catamaran rental in Cancun Isla Mujeres

New
$375/hour
Charter this  53ft Cruising Catamaran for a Boat Party in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

Charter this 53ft Cruising Catamaran for a Boat Party in Cancún, Quintana Roo

New
$466/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$154+/hour
Private Lunch Tour Deluxe in Curacao
Sailing in Santa Barbara Plantation · 6 guests

Private Lunch Tour Deluxe in Curacao

New
$299/hour
Velero Montainer 45ft Sailboat in Puerto Vallarta
Sailing in Isla Iguana · 15 guests

Velero Montainer 45ft Sailboat in Puerto Vallarta

New
$154/hour
😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
Events in Sosúa · 18 guests

😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

New
Superowner
Best of 2026
$75/hour
Gorgeous Private Catamaran for 25 People Open bar
Sailing in Cancún · 25 guests

Gorgeous Private Catamaran for 25 People Open bar

New
$247/hour
Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida
Events in Key West · 12 guests

Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida

New
$14,750/night
Charter The AKKA 68ft catamaran
Sailing in Oranjestad-West · 15 guests

Charter The AKKA 68ft catamaran

New
$700/hour
 Party Boat that can host 150 people in La Romana, Dominican Republic
Events in La Romana · 150 guests

Party Boat that can host 150 people in La Romana, Dominican Republic

New
Superowner
Best of 2026
$100/hour
Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop
Sailing in Fairhaven · 6 guests

Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop

5.0
$150/hour
Turks & Caicos Private Sunrise 27' Sea Ray Boat Charter
Powerboats in The Bight Settlement · 10 guests

Turks & Caicos Private Sunrise 27' Sea Ray Boat Charter

New
$525/hour
Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
Events in Miami · 13 guests

Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

New
$250/hour
40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay
Sailing in Saint Petersburg · 12 guests

40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay

New
$350+/hour
Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

New
$249/hour
44' Beneteau Sailboat for Charter in Kemah, Texas
Sailing in Kemah · 6 guests

44' Beneteau Sailboat for Charter in Kemah, Texas

New
$250/hour
Sunseeker 120 Super Yacht in Cancun. Super Yacht Crew
Events in Cancún · 40 guests

Sunseeker 120 Super Yacht in Cancun. Super Yacht Crew

New
Superowner
$42,000/hour

Sailing Reviews in United States

  1. PM

    Prince

    Affordable Yacht 27' Doral in Toronto

    Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.

  2. BG

    Ben

    Affordable Yacht 27' Doral in Toronto

    Gino and his dad took us out on their boat to the island off the city, where they anchored and we could swim into the beach. We got amazing views of the skyline on the way, and then on the way back they took us even closer to the city before looping back to the dock. Great experience!

  3. TI

    Tony

    Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop

    I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.