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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$2,310
Sailboats
Set sail with these traditional wind-powered boats
$115-$1,150
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
$140-$200
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
DK
Dmitri
Charter 36ft Sloop In Westbrook, Connecticut
We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!
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!
MM
Molly
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Captain Alan and his boat are incredible!! We brought a group of girls for a bachelorette trip and spending the day out on the water was SO much fun. Captain Alan was so communicative and helpful throughout the process and leading up to the day of our charter. He had everything we could have needed on board and was so helpful the whole trip!! His deckie was also so incredibly helpful - we could not have asked for a better time!!! He even had floats and a paddleboard to use which was awesome. Highly recommend to anyone looking for a fun day on the water!! 10/10, no notes!!
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.
Chanel
Classic Motor Yacht in Hampton's, Long Island
This boat was perfect for a girls day on the water! John is a great communicator and captain brandon was amazing! We couldn’t have asked for a better time on the water.
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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November 23, 2022
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December 11, 2020
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