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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,245 Reviews)

Page 7 of 40949 listings

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
Luxury Sailing from Navy Pier Marina
Sailing in Chicago · 8 guests

Luxury Sailing from Navy Pier Marina

5.0
Superowner
$200+/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
Instant Book
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
$650/hour
Newport Harbor Sailing Adventure
Sailing in Newport Beach · 6 guests

Newport Harbor Sailing Adventure

5.0
$133/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
Award winning 41' Hunter Sailboat
Sailing in Marina del Rey · 12 guests

Award winning 41' Hunter Sailboat

4.0
$265+/hour
Beatiful Catalina 42' Yacht Rental in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Beatiful Catalina 42' Yacht Rental in Puerto Vallarta

5.0
Superowner
Best of 2025
$138+/hour
“Exclusive Escape, Unlimited Adventure on our Yacht”
Events in Miami · 14 guests

“Exclusive Escape, Unlimited Adventure on our Yacht”

5.0
$250/hour
Instant Book
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!
Sailing in Marina del Rey · 12 guests

BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

5.0
Superowner
$425/hour
42ft Catalina MkII Sailing Yacht in The San Diego Bay, California
Sailing in San Diego · 6 guests

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

5.0
$285/hour
FULLY CUSTOMIZABLE Luxury Catamaran Charter
Sailing in Nassau · 12 guests

FULLY CUSTOMIZABLE Luxury Catamaran Charter

5.0
$665/hour
DAYTRIP/SLEEP ON BOARD TO CATALINA
Sailing in Los Angeles · 12 guests

DAYTRIP/SLEEP ON BOARD TO CATALINA

4.9
Superowner
$199/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$146/hour
Boat Rental On Lake Washington - 19ft Sea Ray
Powerboats in Renton · 8 guests

Boat Rental On Lake Washington - 19ft Sea Ray

4.0
$150/hour
Instant Book
Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
Best of 2025
$800/hour
Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico
Sailing in Ildefonso Green · 10 guests

Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico

5.0
$550/hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$120/hour
Sailing Trips out of La Conner, Washington
Sailing in Anacortes · 8 guests

Sailing Trips out of La Conner, Washington

5.0
$500/day
Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California
Sailing in Marina del Rey · 12 guests

Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California

5.0
Superowner
$650/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away
Sailing in Nuevo Vallarta · 18 guests

Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away

5.0
Superowner
Best of 2025
$238+/hour
Instant Book
2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Powerboats in Holmes Beach · 8 guests

2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!

4.9
$372+/day

Sailing Reviews in United States

  1. CM

    Caley

    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

  2. Ben

    Ben

    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!

  3. Tarik

    Tarik

    Cruising Monohull Rental in Kingston

    Great sail. Our captain Rob was very knowledgeable and easy to talk to. He let us help with some of the sailing and then we sat at the front of the boat and enjoy the view. It was a perfect day weather wise. Had a great time overall.

  4. EC

    Emily

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

    Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!

  5. RK

    Rosie

    Sailing Trips out of La Conner, Washington

    This was a great experience! Terje was a great guide and captain. Thank you for sharing your knowledge about boating and the area. It was a dream come true for my Dad‘s 82nd birthday.

  6. DL

    Dana

    Cruising Monohull Rental in Kingston

    Excellent trip, exactly as described if not better! Karin convinced us to sail at sunset and it was absolutely beautiful. Do not hesitate to book!