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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,241 Reviews)

Page 16 of 40938 listings

41ft Sailing Charters from Costa Mujeres, Cancun
Sailing in Isla Mujeres · 32 guests

41ft Sailing Charters from Costa Mujeres, Cancun

5.0
Superowner
$248/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
$138+/hour
Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building
Sailing in Vancouver · 8 guests

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

5.0
$179/hour
Limited Availability
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
Limited Availability
35' Beneteau Sailing Yacht For Rent Newport (MAP: 2022-32)
Sailing in Newport Beach · 10 guests

35' Beneteau Sailing Yacht For Rent Newport (MAP: 2022-32)

5.0
$100+/hour
Private Luxury Sunset Sailing Cruise in Cozumel, Mexico
Sailing in San Miguel de Cozumel · 35 guests

Private Luxury Sunset Sailing Cruise in Cozumel, Mexico

5.0
$465/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$275/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
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
$357/hour
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.

4.5
Superowner
Best of 2026
$520/hour
Private 44ft Catamaran Charter for Up to 45 Guests
Sailing in Cancún · 45 guests

Private 44ft Catamaran Charter for Up to 45 Guests

5.0
Superowner
$343+/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
Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Private 37ft Catamaran Charter in Cancún for up to 25 Guests

5.0
Superowner
$157+/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 6 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
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
$203/hour
Blue Lagoon Catamaran 43ft Cat in Cabo San Lucas
Sailing in Marina · 20 guests

Blue Lagoon Catamaran 43ft Cat in Cabo San Lucas

New
$445/hour
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/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
Limited Availability
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
Limited Availability
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
42' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 25 guests

42' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$366+/hour
Private sailing tour in Cancún Mexico
Sailing in Isla Mujeres · 8 guests

Private sailing tour in Cancún Mexico

5.0
$150/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

Sailing Reviews in United States

  1. Ally

    Ally

    44' Catamaran Party Boat In Grand Bahamas Island

    Captain Rico was amazing! He made sure we were taken care of and having fun the whole day. The food was great and the itinerary was perfect. Would 100% recommend and book with him again! We all had so much fun. Thank you Captain Rico!

  2. JS

    Jasmine

    42' Lagoon Luxury Catamaran Charter in Riviera Maya

    FIVE STARS!!! The team was amazing and definitely made the experience even in choppy waters! Christina was a very knowledgeable and awesome rockstar and was proactive in crazy situations we threw at her and the team! Definitely book with them!

  3. Julia

    Julia

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    Paul is personable while also extremely professional. He is obviously very familiar with his boat and we felt very safe during our entire trip. He’s super adept at spotting whale blows and spotting wildlife in general, which allowed us to spot an entire orca family. Amazing experience overall, and I would especially recommend Paul if you’re looking to learn how to sail!

  4. AB

    Anthony

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    What a fantastic day! Paul is a very experienced sailor and made the trip both educational and extremely fun! Paul is a fantastic teacher and everyone had a chance to sail the boat and feel the wind in our hands. I would recommend Paul to anyone. Great for a corporate event, or a romantic day on the water with your significant other. Can't wait until next time!

  5. AW

    Andrea

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    We can’t say enough good things about our wonderful experience with Paul. From the first inquiry, his communication and responsiveness was outstanding. We encountered some challenges with our original plans and Paul went above and beyond to coordinate with us to make our trip possible. He brought the Radiance to pick up our group in a new location which required him to overnight in that location the evening before so that he could ensure that he would be able to meet us at the appropriate time. It was an extremely important and special trip for our family and he went to great lengths to make sure all went smoothly. It was a pleasure to spend our day with him and we are incredibly grateful for his expertise and outstanding customer service. We eagerly look forward to our next sail with Paul!

  6. JH

    Johnny

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    Paul was excellent. Had a great day and did some fun sailing. Paul is very knowledgable and happy to teach as much or as little as you like. The boat was in great condition, very clean and organized. Paul was generous with his time and catered to exactly what we wanted to do for the day.