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The Best Sailboat Rentals in Connecticut
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Connecticut
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$2,160
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$200-$1,280
Fishing Charters
Let a captain do the driving while you do the fishing
$140-$200
Kayaks
Who says you need a motor to have fun on the water?
$25-$1,000
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$140-$200
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$165-$300
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$500
Top Sailboat Rental Locations Near Connecticut
Recent Reviews in Connecticut
Nehal
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
Mark’s boat is spacious. I had booked the boat during the sunset hours and the views were amazing. Mark provides detailed instructions for the pickup and is very punctual.
RA
Reyoof
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
We had an amazing time! Mark was so professional and caring, and did everything he could so we can have the best time. Definitely going again!
MB
Mark
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.
SB
Scott
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
What a day on the water! Our Group of 7 people had an awesome time Captain Brian & Erin. The Catamaran was huge! The sun deck and the interior were clean and full of amenities. The Sailing around Sag Harbor and Shelter Island was something that we will never forget.
EC
Erica
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
Mark was absolutely fantastic! He was in great communication with me for the planning, was extremely flexible with the departure time given the weather forecast within the days before, and overall made it the best sailing experience possible! The boat was in incredible condition and surpassed what is even pictured. I couldn’t recommend him more and we will definitely be sailing with him again
DD
Daniel
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
Booked Mark’s boat for a maternity photo shoot. Everything was perfect! He was very communicative and made the whole process very easy. He even came to pick us up from the beach. The boat is gorgeous and we had an amazing time. Would definitely recommend. Thanks Mark!
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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