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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,354 Reviews)

Page 26 of 38912 listings

Private Sunset Dinner Cruise Belize – Chef & Luxury Experience
Powerboats in San Pedro · 4 guests

Private Sunset Dinner Cruise Belize – Chef & Luxury Experience

New
$340/hour
SEXY 35 ft. SUNDANCER in Cancun With 1 hour Free Jetski
Events in Cancún · 10 guests

SEXY 35 ft. SUNDANCER in Cancun With 1 hour Free Jetski

New
$169/hour
3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests
Sailing in Nassau · 12 guests

3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests

New
$4,800/hour
Luxury Catamaran Belize, Private Chef & Hol Chan Snorkeling
Powerboats in San Pedro · 12 guests

Luxury Catamaran Belize, Private Chef & Hol Chan Snorkeling

New
$882/hour
38ft Lagoon Catamaran Sailing Lessons in Chicago
Tours in Chicago · 6 guests

38ft Lagoon Catamaran Sailing Lessons in Chicago

New
$350+/hour
All inclusive Bali 4.4 Luxury Catamaran Charter
Sailing in Nassau · 10 guests

All inclusive Bali 4.4 Luxury Catamaran Charter

New
$720/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
$494/hour
Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people
Sailing in Cartagena · 17 guests

Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people

New
$180/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
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
Lagoon 440 Catamaran rental in Cancun Isla Mujeres
Sailing in Cancún · 25 guests

Lagoon 440 Catamaran rental in Cancun Isla Mujeres

New
$375/hour
Classic Sailing 39ft Vessel for cruising with style at PV.
Sailing in Marina Vallarta · 12 guests

Classic Sailing 39ft Vessel for cruising with style at PV.

New
$136/hour
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/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
⛵️  MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
Events in Miami Beach · 49 guests

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

New
Superowner
$750+/hour
42' Lagoon Catamaran | Open Bar + Water Toys | Up to 20 Guests
Sailing in La Cruz de Huanacaxtle · 20 guests

42' Lagoon Catamaran | Open Bar + Water Toys | Up to 20 Guests

New
$1,446/hour
Gorgeous Private Catamaran for 25 People Open bar
Sailing in Cancún · 25 guests

Gorgeous Private Catamaran for 25 People Open bar

New
$262/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
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$156+/hour
Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises
Events in Miami · 14 guests

Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises

New
$250/hour
Private Lunch Tour Deluxe in Curacao
Sailing in Santa Barbara Plantation · 6 guests

Private Lunch Tour Deluxe in Curacao

New
$299/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
Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

New
$125/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

Sailing Reviews in United States

  1. 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.

  2. 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.

  3. 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!