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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,289 Reviews)

Page 14 of 39925 listings

42' Trimaran Rental in Cabo San Lucas, Mexico
Events in Marina · 45 guests

42' Trimaran Rental in Cabo San Lucas, Mexico

5.0
$720/hour
Limited Availability
47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay
Sailing in Seabrook · 12 guests

47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

5.0
$300/hour
Limited Availability
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests

4.4
Superowner
$157+/hour
Limited Availability
Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/hour
Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch
Sailing in Cancún · 40 guests

Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch

5.0
$60/day
Leopard 51 Flybridge Power Catamaran in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 Flybridge Power Catamaran in Tulúm

5.0
Superowner
$607+/hour
Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
Sailing in Chicago · 10 guests

Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

5.0
Superowner
$250/hour
Instant Book
Limited Availability
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
$190/hour
Limited Availability
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar
Sailing in Cancún · 55 guests

Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar

5.0
$491+/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
High Demand
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta
Sailing in Marina Vallarta · 8 guests

Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta

New
Superowner
$125/hour
55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo

5.0
Superowner
$400+/hour
Limited Availability
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Sailing in San Francisco · 6 guests

Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

5.0
Superowner
$400+/hour
Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks
Sailing in Guanacaste Province · 20 guests

Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks

5.0
$430/hour
Limited Availability
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

5.0
$1,560/hour
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
Romantic city lights trip on beanbags on 42 ft Bertram
Events in Long Beach · 6 guests

Romantic city lights trip on beanbags on 42 ft Bertram

5.0
$125/hour

Sailing Reviews in United States

  1. AV

    Ariel

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

  2. Erika

    Erika

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.

  3. MS

    Mary Beth

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Excellent trip! Friendly and experienced Captain and first mate! My family and I had a lovely time on a beautiful day! Book today - you will be happy you did!

  4. SV

    Stacey

    42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

    Nate is truly the best of the best if you’re looking to book a boating experience! There are individuals who distinctly stand out for good reason and Nate is one of them through and through.

  5. AW

    Avery

    Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests

    SOOOOO much fun!!!!!!! We would do this many more times with this crew. So attentive and fun. Luna and Alex were great. Highly recommend.

  6. JH

    Julie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    A great day on the bay with Alberto and Grace. They are lovely and wonderful hosts—and a super safe and accommodating Captain/ First Mate!!