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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,083 Reviews)

Page 9 of 39919 listings

Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat

5.0
$2,500/hour
Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

5.0
Superowner
$480/hour
DAYTRIP/SLEEP ON BOARD TO CATALINA
Sailing in Los Angeles · 12 guests

DAYTRIP/SLEEP ON BOARD TO CATALINA

4.9
Superowner
$199/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
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
High Demand
San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests
Sailing in San Diego · 12 guests

San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests

5.0
$300+/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
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
$1,000/day
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
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
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
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in Playa del Carmen · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$268+/hour
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way
Events in Cancún · 20 guests

Sunseeker 60ft Motor Yacht - Free Pick Up Transportation Hotel Marina One Way

4.8
$330/hour
Instant Book
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

5.0
$165/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
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
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/hour
🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/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

Sailing Reviews in United States

  1. SK

    Sean

    Puget Sound Sailing Adventure on 32' Hunter Sailboat

    Russ was outstanding from start to finish. Such an incredible human and captain. Our family spent 3 beautiful hours filled with incredible beauty and wonderful conversation with Russ. It exceeded all of our expectations and was a perfect way to escape the chaos and enjoy the tranquil vibes of the ocean. Top notch from start to finish. We highly recommend Russ and Dylan.

  2. Kelly

    Kelly

    Well Appointed Beneteau 32, Folly Beach, SC

    Greg is an amazing captain!! He’s chill, fun, and so accommodating! We used the boat for our engagement pics and he couldn’t have been nicer to us and our photographer. We would definitely go on his boat again in a heartbeat!!!

  3. BH

    Bibiana

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

    We are still talking about our time aboard The Genesis! Eric was so welcoming to our family, ages 2 - 70! A true sailor, Eric took us on a two-hour sail from Chelsea Piers to the Statue of Liberty. He shared his endless knowledge about NYC as we passed spots of interest on the shoreline. Eric was super kind and patient with our 5-year-old grandson, allowing him to steer the boat. That experience was priceless. The Genesis is a wonderful sailboat that has been lovingly and meticulously cared for. Thank you, Eric, for helping us celebrate Nick's 70th birthday. It was perfect!

  4. JG

    Jen

    Well Appointed Beneteau 32, Folly Beach, SC

    Loved our sunset cruise with Greg for my friends birthday. Beautiful boat, scenery, and weather! It was so relaxing to sail, watch the dolphins and catch a gorgeous sunset on the water. Greg was super nice, took pics of our group, and made the trip more enjoyable with his easygoing personality. We would sail again with Greg anytime!

  5. Angela

    Angela

    Well Appointed Beneteau 32, Folly Beach, SC

    We cannot say enough about Greg! He’s knowledge of sailing, the area, and the ability to make you feel like you’re at home on his beautiful boat. Your mistake would be not having Greg as your captain! Thank you for a wonderful experience and look forward to the next time!!!!

  6. LW

    Lori

    Well Appointed Beneteau 32, Folly Beach, SC

    Captain Greg gave us the best experience for our first time sailing!! Not only was he extremely nice and fun, but very educational! The Water Music is a beautiful sail boat and we felt extremely safe on board with Captain Greg. The whole experience was relaxing with just absolutely stunning sunset views. We can't wait to go sailing again with Captain Greg!!