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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,497 Reviews)

Page 17 of 40 • 951 listings

Now available: 53" Carver Yacht for spring and summer sunset & day cruises
Events in Galveston · 12 guests

Now available: 53" Carver Yacht for spring and summer sunset & day cruises

5.0
$400/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour
40ft Catamaran Private Charter / Capacity 30 people
Sailing in Cancún · 30 guests

40ft Catamaran Private Charter / Capacity 30 people

5.0
Superowner
$275+/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
Boat for Groups of up to 60 People in Cancún, Quintana Roo
Events in Cancún · 61 guests

Boat for Groups of up to 60 People in Cancún, Quintana Roo

5.0
$192/hour
44' Catamaran Party Boat In Grand Bahamas Island
Sailing in Bell Channel Bay · 45 guests

44' Catamaran Party Boat In Grand Bahamas Island

4.6
$140/hour
42' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 25 guests

42' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$345+/hour
Fountaine Pajot 38ft Catamaran in Isla Mujeres Fountain Pajot
Sailing in Centro - Supmza. 001 · 18 guests

Fountaine Pajot 38ft Catamaran in Isla Mujeres Fountain Pajot

5.0
$250/hour
Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2
Sailing in Marina del Rey · 6 guests

Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2

New
$150/hour
Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!
Events in Cabarete · 100 guests

Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!

New
Superowner
Best of 2026
$17/hour
Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington
Tours in Anacortes · 6 guests

Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

5.0
$200/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 6 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
Private Sailing Tours in Playa Flamingo, Guanacaste
Sailing in Playa Flamingo · 17 guests

Private Sailing Tours in Playa Flamingo, Guanacaste

5.0
Superowner
$186+/hour
100' Cruising Catamaran with Unlimited Food and Drinks in Cabo San Lucas
Sailing in Marina · 130 guests

100' Cruising Catamaran with Unlimited Food and Drinks in Cabo San Lucas

5.0
$60/day
Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”
Sailing in Chicago · 10 guests

Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

5.0
$275/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/hour
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained

5.0
$300/hour
Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat
Sailing in Marina · 10 guests

Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

5.0
$150/hour
Private sailing tour in Cancún Mexico
Sailing in Isla Mujeres · 8 guests

Private sailing tour in Cancún Mexico

5.0
$150/hour
23' Ranger Daysailer in Oakland, California
Sailing in Oakland · 5 guests

23' Ranger Daysailer in Oakland, California

5.0
$70/hour
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Sailing in North Vancouver · 10 guests

Charter Jeanneau 50 DS Sailing Yacht in English Bay

5.0
$351/hour
40ft Private Catamaran in Riviera Maya – Up to 20 Guests
Sailing in Puerto Aventuras · 20 guests

40ft Private Catamaran in Riviera Maya – Up to 20 Guests

New
$465+/hour
Beautiful & Luxury 44 Lagoon New Catamaran in Cozumel / Private Tour in Cozumel
Sailing in San Miguel de Cozumel · 30 guests

Beautiful & Luxury 44 Lagoon New Catamaran in Cozumel / Private Tour in Cozumel

5.0
$505/hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150/hour

Sailing Reviews in United States

  1. LA

    LisaMarie

    Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

    We had the pleasure of sailing with Nat over the 4th of July weekend, and it was a fantastic experience from start to finish. He was punctual, courteous, and instantly put us at ease with his friendly demeanor. What stood out most was how attentive he was to our individual experience levels on the water — he adjusted his approach throughout the day so that everyone, regardless of sailing background, felt comfortable and included. Nat is clearly a highly accomplished sailor, but he wears that expertise lightly. The day felt relaxed as we navigated the waters of the San Juan Islands. — great conversation, great skill, and a great time on the water.

  2. Jill

    Jill

    42' Lagoon Luxury Catamaran Charter in Riviera Maya

    Don’t even second guess to rent this boat. We got married and the experience was so amazing and the whole crew made out day so unforgettable. WOW. Thank you

  3. Becca

    Becca

    Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

    Amazing in every way! Kip & Elizabeth were so kind and accommodating. We got to relax, snorkel, and even saw some dolphins which made the trip extra memorable. Kip was always responsive to messages and the process couldn’t have been more seamless from start to finish. Couldn’t recommend enough!

  4. AB

    Anna

    44' Catamaran Party Boat In Grand Bahamas Island

    Our excursion with Captain Rico was great! We were a group of 25 that had some special requests and he was very accomodating. He knew I was concerned about making it back to the cruise ship on time but was able to get in all the fun acitivities. Snorkeling, private beach and jet skiing. The group agreed it was the highlight of the cruise!

  5. Ani

    Ani

    42' Lagoon Luxury Catamaran Charter in Riviera Maya

    We had the absolute pleasure of renting Chris’s catamaran for my husband’s 40th birthday in Tulum, and it was nothing short of phenomenal. The boat itself was beautiful and spacious, but what truly made the experience unforgettable was Chris and his incredible staff. They were superb—attentive, professional, and went above and beyond to make sure every detail was perfect. From start to finish, we felt taken care of, and our group had the best time out on the water. If you’re looking for an unforgettable experience in Tulum, I can’t recommend Chris and his team enough!

  6. Shardae

    Shardae

    Fountaine Pajot 38ft Catamaran in Isla Mujeres Fountain Pajot

    We THE BEST TIME!!! Me and a group of 10 couldn’t express our gratitude enough. I am a travel agent and customer service is crucial. This company did not disappoint on any level. From A to Z we were taken care of. The crew was simply amazing!!!!! The food was great, the atmosphere was phenomenal and you will be apart of our memories forever. Please book them!!!