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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$600
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$325
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$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!
CH
Cynthia
Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!
Aden
Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
Mark was super cool, and we had a great time overall. The only issue was that the zodiac boat at the front was blocking access to the bow, so we couldn’t use that part of the boat. We also wanted to swim, but there was probably a miscommunication — we ended up eating during the time we should’ve been swimming, and later Mark said it was too late. That was a bit disappointing, as we didn’t get to swim at all during our 4-hour trip. Everything felt safe and nice overall. Mark let us play any music we wanted, and everything was clean. A longer trip with more time would definitely be a better option next time.
GB
Gillian
The Only 40ft Hinckley Sailboat in Manhattan
This was such a great experience. Andy was wonderful and the boat is absolutely lovely. I would highly recommend this to anyone looking to book a boat outing. It was such great value for the experience and we had a wonderful time
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!!
GE
Glenda
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
This charter was the perfect little getaway—a mini vacation on the water that left us completely refreshed. The boat was exactly as described: clean, comfortable, and clearly cared for with pride. Every moment felt relaxing and easy, from the smooth ride to the peaceful surroundings. It was the kind of experience that makes you forget about everything else for a while—in the best way. Highly recommend for anyone needing a short but sweet escape.
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!
August 01, 2023
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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