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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,668 Reviews)

Page 23 of 451,076 listings

Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA
Sailing in Oxnard · 6 guests

Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA

5.0
$363-$475hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Treasure Island · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

New
$315-$600hour
Catamaran Lose 50 Casa de Campo La Romana
Sailing in La Romana · 20 guests

Catamaran Lose 50 Casa de Campo La Romana

New
$2,088day
Amazing Cruising Catamaran in Cabo San Lucas, Mexico
Sailing in Marina · 30 guests

Amazing Cruising Catamaran in Cabo San Lucas, Mexico

New
$550hour
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

New
$542hour
Sailboat tour Los Angeles up to 6 people.
Sailing in Marina del Rey · 6 guests

Sailboat tour Los Angeles up to 6 people.

5.0
$113-$179hour
50ft Sailing Catamaran Private Charter / Capacity 50 people
Sailing in Cancún · 50 guests

50ft Sailing Catamaran Private Charter / Capacity 50 people

5.0
$314-$450hour
Luxury Private Sail Yacht rental for groups and families up to 15 Pax
Sailing in Isla Mujeres · 15 guests

Luxury Private Sail Yacht rental for groups and families up to 15 Pax

5.0
$129hour
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123-$245day
Private Charter Curacao Day Tour All-in
Sailing in Jan Thiel · 8 guests

Private Charter Curacao Day Tour All-in

New
$274person
Private Sunset Cruise (2-Hours) in Destin, Florida
Powerboats in Destin · 6 guests

Private Sunset Cruise (2-Hours) in Destin, Florida

5.0
$175hour
45 Sea Ray Flybridge available for rent in Cabo San Lucas
Events in Marina · 12 guests

45 Sea Ray Flybridge available for rent in Cabo San Lucas

New
$350hour
Beautiful 42Ft Express Cruiser yacht in Puerto Vallarta
Events in Isla Iguana · 15 guests

Beautiful 42Ft Express Cruiser yacht in Puerto Vallarta

New
Snoozed - Active 02 Jan 2025
36 YELLOWFIN   Sunset Cruises / Sandbar Party / Intercoastal Cruise
Fishing in Bay Pines · 6 guests

36 YELLOWFIN Sunset Cruises / Sandbar Party / Intercoastal Cruise

5.0
$150hour
41' Gulf Star Monohull Sailing Adventures with Five Star Service and Dinning in Guanacaste
Sailing in Guanacaste Province · 12 guests

41' Gulf Star Monohull Sailing Adventures with Five Star Service and Dinning in Guanacaste

5.0
$100person
Pigs, Turtles, Snorkeling Beach Day
Powerboats in Nassau · 18 guests

Pigs, Turtles, Snorkeling Beach Day

New
$225person
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125hour
Luxury Experience 29ft Titan Yacht in La Cruz de Huanacaxtle, Mexico
Events in Punta de Mita · 8 guests

Luxury Experience 29ft Titan Yacht in La Cruz de Huanacaxtle, Mexico

5.0
$300-$366hour
Crewed Charter on 42' Lagoon Sailing Catamaran from Playa del Carmen
Sailing in Playa del Carmen · 20 guests

Crewed Charter on 42' Lagoon Sailing Catamaran from Playa del Carmen

5.0
$750hour
"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo
Sailing in Tamarindo · 70 guests

"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo

5.0
$75person
Custom Catamaran with food and open bar
Sailing in Cancún · 45 guests

Custom Catamaran with food and open bar

New
Snoozed - Active 02 Jan 2025
Luxury Experience with 40ft Sailboat | Puerto Vallarta
Sailing in Isla Iguana · 14 guests

Luxury Experience with 40ft Sailboat | Puerto Vallarta

New
$200-$220hour
Luxury Experience with a 38ft  Sailboat | Puerto Vallarta
Sailing in Isla Iguana · 8 guests

Luxury Experience with a 38ft Sailboat | Puerto Vallarta

New
$160-$220hour
Classic Formosa 51 Sailing Boat Rental in Santa Marta, Magdalena
Sailing in Comuna 2 · 26 guests

Classic Formosa 51 Sailing Boat Rental in Santa Marta, Magdalena

5.0
$50person

Sailing Reviews in United States

  1. JF

    Joey

    Private Sunset Cruise (2-Hours) in Destin, Florida

    Ladd was our captain for this trip. We couldn’t ask for a better crew than him and Sebastian. We had to delay our trip a day because of a storm but they more than made up for it. They also documented our trip with photos that they emailed to us. It was very relaxing and informative. We also got to see some dolphins. Very nice people. Overall, a 10 star outing!

  2. KW

    Kel

    Private Sunset Cruise (2-Hours) in Destin, Florida

    This was a GREAT trip..Captain Tracy's communication and follow thru was awesome.. although Tracy was unable to captain the boat Captain Ladd and Sebastian created an awesome experience for my girlfriend and I.. we even got up close and personal with the dolphins...I would definitely recommend and will use again

  3. EG

    Eva

    36 YELLOWFIN Sunset Cruises / Sandbar Party / Intercoastal Cruise

    We had an extraordinary experience on the the Skirt Chaser for a 4 hour boat trip with Captain Frank and his adorable pup Chaser! Along the way we encountered dolphins, school of stingrays and beautiful waterways including stop at Shell Key island. Do not hesitate to book a private experience it’s worth every penny. Captain Frank delivers a wonderful experience and we will return. Maybe next time we will try a deep water fishing excursion instead of a leisurely boat experience. Thank you for creating life long memories for our family.

  4. LC

    Louis

    41' Gulf Star Monohull Sailing Adventures with Five Star Service and Dinning in Guanacaste

    Incredible sailing experience, look no further and book. From start to finish Hugo and the fellow two crew members were incredible guides, and the itinerary they drafted was spectacular. Great value and every step of the way was incredible. Food and drinks very good as well, and a very safe experience. Also compared to other options the best value in Guanacaste. Will be back!!

  5. dh

    deborah

    Cruising Monohull Rental in Kingston

    We had a wonderful time sailing with Karins family! They were very friendly, easygoing and so knowledgeable, made us very comfortable and they were great about social distancing/COVID conscious. We were able to relax and enjoy the ride at the bow with comfy seats provided and we brought our own snacks. The weather was beautiful and the whole experience couldn’t have been better. Definitely a highlight of our stay in Kingston. We can’t wait to be back for another sail! Many thanks :)

  6. KF

    Kalene

    36 YELLOWFIN Sunset Cruises / Sandbar Party / Intercoastal Cruise

    Terrific sunset cruise and a chance to see the Skyway bridge up close at night were a great way to celebrate our anniversary! Capt Frank was very accommodating and made sure we had a great time. Awesome music and vibe! Highly recommend!