We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

$100-$300
All listings in the United States

Awesome sailboat rentals in United States.

4.9
(5,173 Reviews)

Page 1 of 22513 listings

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
Superowner
$105-$125hour
Privat 30’ Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Sailing Yacht in Mazatlan Bays & Islands

5.0
$149hour
Spacious, fast 80 foot sailboat with a hot tub
Events in Marina Vallarta · 40 guests

Spacious, fast 80 foot sailboat with a hot tub

5.0
$275hour
😍Experience Peace and Tranquility 😍🍷🍾
Sailing in Coronado · 4 guests

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100-$150hour
Privat Sunset  Sailing
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0
$119hour
Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran
Sailing in Las Terrenas · 15 guests

Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran

New
Best of 2023
$278hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2023
$210-$325hour
40' Luxury Catamaran in Cozumel
Sailing in San Miguel de Cozumel · 20 guests

40' Luxury Catamaran in Cozumel

5.0
Superowner
$290hour
🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing
Sailing in Samaná Province · 12 guests

🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing

5.0
$197hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
$255-$285hour
Instant Book
Private 35' Catamaran Sailing to Isla Mujeres
Sailing in Cancún · 15 guests

Private 35' Catamaran Sailing to Isla Mujeres

5.0
Superowner
$190hour
⛵ Lagoon 40 Yacht Catamaran in Puerto Vallarta
Sailing in Marina Vallarta · 15 guests

⛵ Lagoon 40 Yacht Catamaran in Puerto Vallarta

5.0
Superowner
Best of 2023
$238-$300hour
⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

5.0
Superowner
Best of 2023
$250-$325hour
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$115hour
Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe $500
Sailing in Placer County · 4 guests

Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe $500

5.0
$200hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150-$190hour
Beatiful Sailboat Sloop 40 ft in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Beatiful Sailboat Sloop 40 ft in Puerto Vallarta

New
Superowner
Best of 2023
$135hour
Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible
Sailing in Jan Thiel · 30 guests

Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

5.0
$100person
Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2023
$160-$175hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$200hour
⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 41ft 🐳 🌴 luxury service🛥️
Sailing in Playa del Carmen · 20 guests

⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 41ft 🐳 🌴 luxury service🛥️

5.0
Superowner
$290hour
34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas
Events in Marina · 8 guests

34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas

5.0
$190hour
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0
$150hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2023
$220hour

Sailing Reviews in United States

  1. Janine

    Janine

    Privat 30’ Sailing Yacht in Mazatlan Bays & Islands

    This was the highlight of our whole trip! Jorge is an excellent, well known sailor in the area. He is so kind and knowledgeable, we felt like we already knew him. The boat was spotless and the lunch and drinks were perfect! The sights were breathtaking! Thanks again! We loved our day of sailing.

  2. OV

    Olivia

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    We had the most fantastic photoshoot at sea. Matthew was an amazing captain and the boat is gorgeous. He took us on an amazing trip to capture the best shots, was so thoughtful, helpful, and funny. We felt like we were living in a JCrew ad - we can't wait to come back!

  3. EM

    Emily

    ⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

    Float Boat was an EPIC experience! The planning was casual and easy, vessel was beautiful and clean, the staff was so fun and happy! We blasted music, danced, jumped into the ocean at different locations, visited a beautiful beach, drank yummy margaritas and took shots, snacked on delicious nachos, fresh-caught, made on site ceviche, chips, salsa, guac, quesadillas. 100 % FUN!! The staff took lots of pictures and videos for us and encouraged us to have the best time. 2-3 of the 7 of us ended up so be careful of that, but otherwise it was just hands down fun, wild, adventurous and beautiful! Fernando, Ceasar and Alfredo were the best!!

  4. AM

    Angela

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    Excellent communication and professionalism from Matthew took the stress out of planning this excursion for my 7 year old's birthday trip to CA. The location was great with a nice Marina, wildlife spotting, and beautiful beaches! We really enjoyed our first sailing adventure!

  5. Laura

    Laura

    Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

    Captain Daniel was a wonderful host! The boat is large and spacious with lots of places to sit and relax. There is a grill on the boat and the lunch was fabulous. Nice ride out to the sea and then relaxing in a bay by a small beach. Lots of swimming and snorkeling opportunities. Highly recommend!

  6. Sv

    Skye

    ⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 41ft 🐳 🌴 luxury service🛥️

    We received the warmest welcome from the crew, which made us feel right at home. To get all of the formalities out of the way: the service was impeccable and you definitely get way more than you pay for with this charter! The real reason, however, why we will book a charter with this boat again is the wonderful crew we got to sail with. After we left the boat, we left having made new friends whom we shared an unforgettable experience with!