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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,153 Reviews)

Page 4 of 40937 listings

Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
Privat Sunset  Sailing
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0
$133/hour
Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0
Superowner
$150/hour
🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.
Events in Barrio Las Yaguitas · 150 guests

🤩VIP EXPERIENCE 🎊🎂🛥💕Bachelorette/Birthday Party Power in Sosua Beach.

5.0
$160/hour
Beautiful Jeanneau 58' Sailboat in Marina del Rey
Sailing in Marina del Rey · 8 guests

Beautiful Jeanneau 58' Sailboat in Marina del Rey

4.8
$400/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.8
$150/hour
Big Luxury Catamaran 52 Lagoon Bar Sunset Food Music Snorkelng 4 Rooms Bathrooms
Sailing in Marina · 30 guests

Big Luxury Catamaran 52 Lagoon Bar Sunset Food Music Snorkelng 4 Rooms Bathrooms

5.0
$450/hour
Private Sailboat Beneteau 42ft in Cabo, All-Inclusive
Sailing in Juárez · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0
Best of 2025
$350/hour
SeaRay 320 Yacht Charter in Cabo San Lucas
Events in Marina · 8 guests

SeaRay 320 Yacht Charter in Cabo San Lucas

4.9
$180/hour
Instant Book
SEARAY SLX400 | $800hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0
Superowner
Best of 2025
$800/hour
Instant Book
Elegant 43ft Catamaran: Experience Boston Harbor in Style!
Sailing in Boston · 6 guests

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

5.0
$313+/hour
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$205+/hour
Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México
Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0
$265/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 22 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$427/hour
55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.
Sailing in Marina del Rey · 12 guests

55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.

5.0
Best of 2025
$185+/hour
Schock 35 Cruiser Racer in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35 Cruiser Racer in San Francisco Bay

5.0
$134/hour
42 Sailing Monohull Tours in Sausalito
Sailing in Sausalito · 6 guests

42 Sailing Monohull Tours in Sausalito

5.0
Superowner
$200/hour
Luxury 42ft Sea Ray Motor Yacht Charter for up to 8 people in Cancun
Events in Cancún · 8 guests

Luxury 42ft Sea Ray Motor Yacht Charter for up to 8 people in Cancun

5.0
$133/hour
Instant Book
40 ft Luxury Catamaran Sailing Yacht in Charleston
Sailing in Mount Pleasant · 6 guests

40 ft Luxury Catamaran Sailing Yacht in Charleston

5.0
Superowner
$300/hour
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$178/hour
Sporty Adventure Sailing Catamaran to Catalina Island!
Sailing in Marina del Rey · 12 guests

Sporty Adventure Sailing Catamaran to Catalina Island!

5.0
$225+/hour
Efoiling at deer creek reservoir
Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0
$75/hour
Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 8 guests

Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico

5.0
Superowner
Best of 2025
$119+/hour

Sailing Reviews in United States

  1. OO

    Olivia

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    We had the best time on the boat with Alex, the boat was perfect, plenty of room to move around. The views were stunning, everything went so smooth from the pickup to departure. They accommodated us with everything we needed. Alex and his mate were super knowledgeable and friendly. We had the best time with them and can’t wait to book again’

  2. Brittany

    Brittany

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰

  3. SE

    Sara

    55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.

    We had such a fun time sailing with Captain Stephen! The boat was perfect for our group of eleven and it was so nice getting out on the water. Easy to book and communicative with all our questions — highly recommend if you’re looking for a fun day with friends!

  4. SS

    Sonia

    Sporty Adventure Sailing Catamaran to Catalina Island!

    We had a phenomenal time on the boat and with Captain Sebastian! The boat was stunning and my friends were so shocked. We loved all the different spots on the boat to explore (net in front was a favorite) and take in the Marina. The trip was so easy to book and we had such a great time we will be looking to book again soon!

  5. Brad

    Brad

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!

  6. Van A.

    Van A.

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    A great Milwaukee skyline sail with an old sailor and his 8 and 5 year old grandkids. Patrick was totally accommodating and I was very happy. Toby “loved the ride” And Betty feigned boredom. I know they both loved the experience. Patrick our skipper was great. The boat clean and well cared for.