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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
$225-$3,250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$220-$2,915
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
$160-$780
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50
Top Sailboat Rental Locations Near Middletown
Recent Reviews in Middletown
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.
CQ
Christopher
56' SeaRay Yacht in New York!
Captain Max and Ty were exceptional they went above and beyond for me and my group. They exceeded expectations and the vessel was just as beautiful as the pictures show definitely will be renting with you guys again. One of the best experiences of my lifetime
MA
Melinda
56' SeaRay Yacht in New York!
I highly recommend Captain Max and the Encore yacht. Follow the rules and you'll have an enjoyable time. Throughout the booking process, He is very responsive. It's a beautiful yacht! The main goal is to protect and maintain the yacht while delivering a fun day on the water. First Mate, MJ is amazing...skilled, helpful, and a great personality. You won't regret booking with Captain Max. This private charter saved my 40th birthday celebration since all other plans were cancelled due to covid.
vito
56' SeaRay Yacht in New York!
We recommend this boat 100% took clients for 5 hours around the hudson and the vibe was perfect! Captain was very professional and the crew was super nice ! We had the crew always asking if we need it something! 5 stars for the boat and crew! We will def be back
VL
Van
Sailing NYC aboard 34' Catalina
It's a bit windy but we all enjoyed the view and how friendly and professional Andrew is. He was very kind in helping my friend who has sea sickness. I had a wonderful birthday today on the boat even though it was cold. Also, they kindly waited for me to arrive due to unexpected traffic jam.
CD
Courtney
Sailing NYC aboard 34' Catalina
This was such an incredible experience. The captain was amazing and was very well informed about sailing and NYC. Planned this for a surprise birthday party and it was a fabulous time. I absolutely recommend and hope to do this again soon! Note, bring extra layers becuase it can get very chilly!
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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