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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
$230-$3,200
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$220-$2,985
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$500
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$160-$780
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$100-$300
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$75
Top Sailboat Rental Locations Near Middletown
Recent Reviews in Middletown
MC
Monica
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian is absolutely wonderful. I wanted to celebrate my 30th birthday and it was a rainy weekend, and Ian was SUPER FLEXIBLE in booking around good weather, like he truly and genuinely cared about us having a good experience. Great human!!!
GS
Gurpreet
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian did a great job with our trip. He was able to show us all around nyc and even though we were running close to the sunset, he was able to get us out on the water in time to watch. The boat ride was smooth, he was very accomodating. It was fun chatting with him and he came prepared with blankets, jackets, water if needed. The boat trip itself was smooth with no issues. Would definitely book again, if needed and highly recommend!
JT
Julia
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
We had an amazing experience with Ian! The boat was beautiful and the route we took was too! Ian made sure we were comfortable the whole time, and took good care of us. We couldn’t have asked for any more, it was perfect. Thank you!!
MC
Mike
Sailing NYC aboard 34' Catalina
Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!
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
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!
Real reviews from happy Getmyboaters.
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