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The Best Sailboat Rentals Near Middletown
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Middletown
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$260-$3,350
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$240-$2,760
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$100-$300
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$305-$780
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50
Recent Reviews in Middletown
Abhishek
The Only 40ft Hinckley Sailboat in Manhattan
Captain Andy is one of the best hosts and extremely skilled at what he does. I was planning a proposal for my girlfriend and he went above in beyond in helping us out. He gets back quickly regarding any queries and makes sure you have a memorable experience. I have nothing but good this to say about our experience. Definitely recommend Captain Andy if you are looking for a good time on a sail boat.
AM
Angela
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Wonderful experience with my 2 daughters! They jammed out to their favorite music while enjoying the sights and were given a chance to steer the boat! Ian was attentive and amiable throughout the booking and sailing experience.
AS
Andie
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian and Kim were fantastic hosts, captain and first mate! We used Ian’s vessel for a music video shoot, and not only were they helpful and accommodating, but happy to have us aboard and a part of our production. I highly recommend booking with Ian for a similar situation or if you just wanted a fun outing with some good friends!
Jonathan
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian was a gracious host. Perfect trip and captain. I would highly recommend you use his sailboat!
SR
Sana
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
I had an amazing time. The guy was really nice. I had a great experience.
David
56' SeaRay Yacht in New York!
Had a really fantastic cruise with close friends -5 adults and 2 kids aged 9 and 11. Boat is fabulous, crew was great and Capt. Max was the best from start to finish. Listen to his recommendations - he knows what he’s doing. This was a special trip and one that my group will remember fondly for a long time.
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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