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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$320-$2,515
Sailboats
Set sail with these traditional wind-powered boats
$105-$1,170
Kayaks
Who says you need a motor to have fun on the water?
$325-$400
Fishing Charters
Let a captain do the driving while you do the fishing
$130-$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$130-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$675
AP
Abraham
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing, optional Waverunner
My daughter and her friends had a 16th birthday party on the boat and they had an amazing time. Jeffrey was a wonderful host and the boat was incredible. Everything was exactly as described and it was a amazing experience for everyone.
MC
Mike
Sailing NYC aboard 34' Catalina
Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!
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.
NM
Natalie
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing, optional Waverunner
My friends and I had an incredible time on Jeff’s yacht! He was a fantastic host, always helpful and quick to answer any questions we had before our trip. The boat itself is stunning, with plenty of space to relax and enjoy the day. We can’t wait to book another adventure on board!
RG
Rishan
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing, optional Waverunner
Capt. Jeffrey is as great as it gets! He’s so fast in responding. He was very welcoming, made us feel at home and made sure everybody was having a good time! He has so many water games it made our experience so fun and memorable! The boat has so many areas where you can sit and also where you can sun bathing! We can’t wait to go out with him again!
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 09, 2023
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November 28, 2022
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May 20, 2021
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December 30, 2019
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December 26, 2019
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