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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,051 Reviews)

Page 9 of 39919 listings

Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
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
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
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
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
🤩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
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
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/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
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
Hunter Passage 42' Sailboat - Take your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter Passage 42' Sailboat - Take your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2026
$40/hour
Epic 42ft Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42ft Party Catamaran for Rent in Cabo San Lucas

5.0
$550/hour
Wedding Groups Best Seller 82ft Luxury Catamaran with OPEN BAR UNLIMITED
Sailing in Isla Mujeres · 140 guests

Wedding Groups Best Seller 82ft Luxury Catamaran with OPEN BAR UNLIMITED

5.0
$58+/hour
Limited Availability
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Superowner
$325/hour
Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur
Sailing in Zona Comercial · 6 guests

Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur

New
$120/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/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
MAXUM 46' YACHT FOR RENT IN VANCOUVER
Events in Vancouver · 12 guests

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$367/hour
High Demand
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
$70/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
Beautiful Catalina 42 Sailboat In Puerto Vallarta, México
Sailing in Marina Vallarta · 12 guests

Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

5.0
$130+/hour

Sailing Reviews in United States

  1. SB

    Synetra

    Wedding Groups Best Seller 82ft Luxury Catamaran with OPEN BAR UNLIMITED

    Great experience, accommodating crew, smooth sailing, would recommend highly!!

  2. FH

    Faith

    Epic 42ft Party Catamaran for Rent in Cabo San Lucas

    Our group had a phenomenal time- the crew kept the energy up and made sure we were all taken care of! Even got an extra bonus of a while sighting. 10/10 experience!

  3. NH

    Nikki

    Luxury Sailing Experience on Robertson & Caine Leopard 40

    I’m so glad I decided to book this vessel! Booking was simple. The communication was accurate, timely, always professional, and with forethought, before the trip. My group was in town for a bachelorette weekend and enjoyed our day sailing with Captain Dan. We departed and returned right on time, which we appreciated as we had a schedule we were trying to adhere to. We also appreciated the blankets as it got windy at some points and we didn’t want to go inside. Overall 10/10 experience. I’d definitely book again!

  4. 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 :)

  5. MA

    Marc

    Puget Sound Sailing Adventure on 32' Hunter Sailboat

    Russ is a fun extremely personable great Captain. we could not have asked for a better afternoon on the water in the sailboat. nothing was said to us about what we may see and we had no idea whales would be there and we saw several. 3 within 20ft of the boat. My wife and daughter had never been on a boat before and today was the absolute highlight of their summer and mine too. Thank You Russ for a great wonderful cruise. To anyone giving thought to this sailboat cruise dont wait it is more than worth it in every way. great memories will be made that is for sure. Marc

  6. AD

    Alissa

    Puget Sound Sailing Adventure on 32' Hunter Sailboat

    My husband and I traveled from North Dakota to WA to visit some friends. This was our very first sailing experience and we had so much fun. We were lucky enough to spot a few orcas in Puget Sound. Captain Russ was very nice and accommodating. The boat was beautiful. I would highly recommend booking a cruise with Captain Dylan/Russ if one is ever in the Seattle area. You will not be disappointed. We would definitely book again.