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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,140 Reviews)

Page 9 of 39925 listings

Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
$150/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
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

New
Superowner
Best of 2026
$50/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
3-hour exclusive Catamaran Sunrise or Sunset
Sailing in Isla Mujeres · 16 guests

3-hour exclusive Catamaran Sunrise or Sunset

4.9
Superowner
$262/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 40ft 🐳 🌴
Sailing in Playa del Carmen · 22 guests

⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 40ft 🐳 🌴

5.0
Superowner
$259+/hour
Pure Sport Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Pure Sport Catamaran Sailing on San Diego Bay

5.0
$220/hour
FULLY CUSTOMIZABLE Luxury Catamaran Charter
Sailing in Nassau · 12 guests

FULLY CUSTOMIZABLE Luxury Catamaran Charter

5.0
$600/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht

5.0
Superowner
Best of 2026
$50/hour
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
$300+/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour
Puerto Plata-private And Luxury VIP Party Yachts
Powerboats in Puerto Plata · 100 guests

Puerto Plata-private And Luxury VIP Party Yachts

New
Superowner
Best of 2026
$50/hour
Biggest Brand New 82ft Luxury Catamaran with Open Bar For The Best Time
Sailing in Isla Mujeres · 140 guests

Biggest Brand New 82ft Luxury Catamaran with Open Bar For The Best Time

5.0
$450+/hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$300/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour

Sailing Reviews in United States

  1. KI

    Keoni

    Incredible 36' Cruiser For Rent

    I want to start off thanking God for people like Captain Chris. I had the absolute pleasure of celebrating my 33rd birthday with Captain Chris, and I truly cannot recommend him enough. From start to finish, he exceeded every expectation. His boat was spotless, and his sailing was incredibly smooth—it honestly felt effortless and relaxing the entire time. What stood out the most was his professionalism and kindness. He was extremely accommodating, answered every call leading up to the trip, and made sure we had clear directions and everything we needed. He welcomed everything we brought onboard without any hesitation and never once made us feel uncomfortable or restricted—he simply allowed us to enjoy our time fully. Captain Chris has such a calm and respectful presence that at times we even forgot he was there, yet everything ran perfectly. That balance is rare, and he handled it beautifully. This experience meant more to us than just a birthday celebration. Our family had just experienced a loss, and this day gave us a moment to breathe, laugh, and reconnect. It truly felt like a healing escape, and Captain Chris played a huge role in creating that space for us. It felt like we were in a movie, and he was the one helping bring it all together behind the scenes. I’m beyond grateful for the experience and for his energy, professionalism, and generosity. If you’re thinking about booking—do it. You will not be disappointed. He is absolutely stellar. Thank you again, Captain Chris, for making my birthday unforgettable. 💛

  2. BC

    Breck

    Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

    This is by far the best catamaran experience I’ve ever had! The whole trip, the hospitality, the food, the atmosphere, everything about the entire time spent with Clem and crew was truly incredible. I wholeheartedly recommend this experience to everyone I talk to.

  3. JF

    Joey

    ⭐️ 🎉 PROMO: 1 HOUR FREE ☀️VIP Catamaran 40ft 🐳 🌴

    If I could give higher than 5 stars I would. This team was absolutely incredible. I do a lot of boat trips and this was by far the best one I’ve been on for the price. The team was attentive, fun, and just all around amazing. The food was freshly prepared and delicious. My entire group had nothing but good things to say about our trip. We will definitely be back!

  4. HS

    Hunter

    Sailing From Pompano Beach, FL

    Had a great time celebrating a birthday great clean boat. Cap Mark was a great Time. Highly recommend

  5. JW

    Jessica

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!

  6. 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 :)