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The Best Sailboat Rentals in Middletown
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Top Sailboat Rental Locations Near Middletown
Newport, Rhode Island
19 boats to rent
Jamestown, Rhode Island
20 boats to rent
Narragansett, Rhode Island
23 boats to rent
Montauk, New York
29 boats to rent
Cape Cod, Massachusetts
29 boats to rent
Barnstable, Massachusetts
15 boats to rent
Quincy, Massachusetts
40 boats to rent
Hull, Massachusetts
9 boats to rent
Boston, Massachusetts
54 boats to rent
Sag Harbor, New York
39 boats to rent
Noyack, New York
42 boats to rent
Chatham, Massachusetts
7 boats to rent
Marblehead, Massachusetts
8 boats to rent
Southampton, New York
55 boats to rent
Gloucester, Massachusetts
10 boats to rent
Long Island, New York
62 boats to rent
Fire Island, New York
10 boats to rent
Stamford, Connecticut
8 boats to rent
Recent Reviews in Middletown
SB
Sarah
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Our sail with David was wonderful! He’s so nice and had some great ideas for pictures for our engagement shoot!
MS
Megan
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Captain Dave is awesome. He’s knowledgeable, accommodating, friendly and down to earth. My 5 friends and I had an amazing time sailing in Newport as part of a Bachelorette party, but we all agreed we would do it again any time because it was so fun! I’d highly recommend this experience to anyone!
MB
Mark
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Our sail with David was great! Even though we had light winds, we still covered a lot of ground. David is very capable and knowledgeable, and he also knows a lot about the area and the maritime region. The boat is in very good condition and very roomy. We ended up with 4 guests and were very comfortable. We expect to sail again with David in the future.
MF
Margaret
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Six of us took a lovely sail with Dave as our captain. We sailed out to listen to some of the Newport Jazz Festival and then took a turn around the area. We had so much fun, and Dave was great! He's friendly and knowledgeable about points of interest in the area. We will definitely sail with him on the Hurrah again. Thanks Dave!
HR
Haley
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
David was the best!!! His boat is beautiful, he had so much knowledge and was so great to talk to, he gave us an unforgettable experience! We’re definitely coming back annually to do more boat tours with David! We took our engagement photos on the boat, had champagne and enjoyed the beautiful weather!
Tyra
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
A great experience. David is so communicative and made the entire experience perfect! We had some set back due to a passing shower but David called with updates and made sure everything was safe before it began. He was so full of information and made the experience that much better. Look forward to next time!!
Top Sailboat Rental Locations in the United States
Los Angeles, California
352 boats to rent
Miami, Florida
1009 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
130 boats to rent
Honolulu, Hawaii
47 boats to rent
Oakland, California
43 boats to rent
San Diego, California
112 boats to rent
New York, New York
79 boats to rent
Dania Beach, Florida
234 boats to rent
Annapolis, Maryland
46 boats to rent
Fort Lauderdale, Florida
252 boats to rent
Chicago, Illinois
260 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Charleston, South Carolina
128 boats to rent
Houston, Texas
52 boats to rent
Kemah, Texas
41 boats to rent
Clear Lake Shores, Texas
38 boats to rent
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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