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$100-$300
All listings in the United States

Awesome sailboat rentals in United States.

4.9
(5,059 Reviews)

Page 1 of 22514 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
$105-$125hour
😍Experience Peace and Tranquility 😍🍷🍾
Sailing in Coronado · 4 guests

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100hour
Privat 30’ Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Sailing Yacht in Mazatlan Bays & Islands

5.0
$147hour
Nice Sea Ray Sundancer 32ft in Cabo San Lucas
Events in Marina · 8 guests

Nice Sea Ray Sundancer 32ft in Cabo San Lucas

5.0
$180hour
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
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
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Treasure Island · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
$225-$350hour
40' Luxury Catamaran in Cozumel
Sailing in San Miguel de Cozumel · 20 guests

40' Luxury Catamaran in Cozumel

5.0
Superowner
$275hour
 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
$255-$285hour
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
$275hour
Private 35' Catamaran Sailing to Isla Mujeres
Sailing in Cancún · 15 guests

Private 35' Catamaran Sailing to Isla Mujeres

5.0
Superowner
$190hour
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$115hour
⛵ 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
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
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
$250hour
Privat Sunset  Sailing
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0
$117hour
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
$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
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
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
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
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
⭐️ 🎉 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
🥰 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

Sailing Reviews in United States

  1. VS

    Vaibhav

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian was fantastic! Ian explained everything in detail and was very welcoming. I really enjoyed the experience and hospitality. I wanted to surprise my partner with the trip, and Ian was very accommodating in trying to keep it as last minute as possible. The boat was very well maintained and the ride was extremely smooth. Ian helped me create memories that'd last a lifetime and for that I'd highly recommend him.

  2. JA

    Jason

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

    Fantastic experience! Crew was great, made good drinks and we all enjoyed the ceviche. Would do this again if back in playa or cozumel! Thank you to the crew for being on top of everything! My drink was never empty! The boat was nice and new as well! We enjoyed the sandbar the most!

  3. MF

    Margaret

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

    Mika & co. were all great! From the time my group & I arrived at the marina she was communicative, her and the captain made us feel secured! Just be aware you have to swim to shore LOL, shout out to the captain who helped me swim over to shore cause I was not prepared!😂 Cayo Levantado is beautiful, we ate there & tanned. Overall, the boat ride was smooth & we really enjoyed being on board!

  4. DF

    Damien

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

    Such a beautiful vessel and Matthew is such a kind and knowledgeable captain. He made sure to accommodate us, keep us warm and get us in the best possible positions to get the perfect shot for our engagement photos. I highly recommend booking with him!

  5. Shannon

    Shannon

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    My fiancé & I had our engagement photoshoot on board. I can’t rave enough about how wonderful of an experience that we had. Ian and Kim were both incredibly friendly and professional. 10/10. We will definitely be renting from them again in the near future!

  6. Tasha

    Tasha

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

    We booked this charter for a day in Cozumel with our family of four. It was a VERY full day - we stayed at Kanai and had to take taxi to playa del Carmen, then ferry to Cozumel, ferry, then taxi back. But definitely worth it to see the waters at Cozumel - it was beautiful. The staff were attentive and excellent. Food was plentiful if a little limited with the menu. The ceviche was excellent as was the pineapple pico de gallo. Not great for picky eaters, though. The snorkeling was fun and we really enjoyed anchoring down in the shallower waters to enjoy the paddle board and jumping off the boat.