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Sailboats
Set sail with these traditional wind-powered boats
$115-$1,060
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$200-$2,150
Kayaks
Who says you need a motor to have fun on the water?
$25-$2,315
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$200
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$165-$300
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$195-$200
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$500
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$500
JS
Josh
Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT
Matt was Great! went out with my 8 year-old son, girlfriend and a friend for a three hour trip on the boat. Checked out the beautiful coastline and a couple of awesome swimming holes spent some time on the paddleboard.. such an awesome day. Can’t wait to take another trip out with Matt. Beautiful boat, very professional.!
MP
Merritt
Cruisers 420 Express Cruiser Rental in Long Island Sound
Captain Dirk and his boat made our Fourth of July one to remember! From the moment we stepped on board, Dirk was the picture of professionalism—warm, respectful, and incredibly knowledgeable. I’m 39 weeks pregnant and felt completely safe and cared for the entire time. The boat itself was pristine, spacious, and so comfortable—perfect for taking in the fireworks in style. Dirk went above and beyond to make sure everyone had a great time. Truly one of the best boating experiences I’ve ever had. Can’t recommend him enough!
CS
Courtney
52’ Maxum FlyBridge Yacht - NY & NJ Pick up Available
Glenn and his crew are truly amazing hosts. The trip was everything we wanted and more. Leading up to the trip, Glenn was super responsive, accommodating, and flexible when I needed to change the date and time of the booking. The day of, they took us on a beautiful ride, including a wonderful swimming excursion with floats. It was everything I wanted for my birthday and I would definitely book with Glenn again!
JL
Jaclyn
Overspray in Old Saybrook | 37ft Silverton Yacht
We had a beautiful day out on the CT river for my sister’s birthday! Pick up/drop off was incredibly easy, boat was in great condition, and the crew was very accommodating - would definitely recommend!
PT
Patrick
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Marco is the consummate professional/captain. Flexible on the water with things to do and we all had a blast cruising and diving and swimming in the Sound
Michael
53 ft. Luxury yacht for Day Charters on the East End of Long Island
Very knowledgeable and expert captain!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
April 17, 2024
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August 01, 2023
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October 03, 2022
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December 11, 2019
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August 24, 2023
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April 10, 2020
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