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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,284 Reviews)

Page 10 of 40939 listings

Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity
Sailing in Providence · 6 guests

Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity

New
$150/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

5.0
Superowner
$480/hour
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

5.0
$54/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited
Sailing in Isla Mujeres · 140 guests

Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited

5.0
$511+/hour
🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2026
$40/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/hour
Epic 42ft Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42ft Party Catamaran for Rent in Cabo San Lucas

5.0
$550/hour
MAXUM 46' YACHT FOR RENT IN VANCOUVER
Events in Vancouver · 12 guests

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$351/hour
Luxury Italian Sailing Yacht on the Puget Sound — Seattle
Sailing in Seattle · 6 guests

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

5.0
$374+/hour
Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran
Sailing in San Pedro · 24 guests

Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran

5.0
$400/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/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!

4.8
$250+/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour

Sailing Reviews in United States

  1. Geoffrey

    Geoffrey

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  2. JC

    Janna

    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

    We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.

  3. RK

    Richard

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!

  4. XN

    Xavier

    Luxury Italian Sailing Yacht on the Puget Sound — Seattle

    We had an incredible experience on this sailboat. The boat itself was absolutely immaculate and beautifully maintained, truly the perfect setting. Matt and the captain were both so friendly, welcoming, and made the whole experience even better with their fun banter and great energy throughout. The views were amazing, and everything came together perfectly for our engagement shoot. It honestly could not have been a better experience for my fiancée and me. Highly recommend.

  5. WD

    William

    6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

    My friends and I had a great time cruising around the bay with Ryan. The boat is fast and a great way to get around the bay while taking in the sun and sights.

  6. AS

    Adam

    San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

    Knowledgeable, Friendly, and Fun. 100% recommend, we will be back.