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Sailboats
Set sail with these traditional wind-powered boats
$230-$1,090
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$2,300
Kayaks
Who says you need a motor to have fun on the water?
$310-$2,315
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$225-$2,125
Fishing Charters
Let a captain do the driving while you do the fishing
$225-$2,125
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$500
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$675
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!
SM
Shannon
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Brian was amazing! From the booking to our trip, he was great to work with. Professional and fun. We would recommend him to anyone. Thanks Brian!!
SW
Shannon
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Hands down the best captain experience we've had - very professional, knowledgeable and also fun!
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.
SD
Stuti
52’ Maxum FlyBridge Yacht - NY & NJ Pick up Available
Yacht experience was magical .We really enjoyed celebrating my spouse’s birthday in yacht. Captain and helper did great job taking care of us and hospitality.Yacht is big with second floor where you get magnificent views of NYC skyline and Statue of Liberty. Highly recommend this yacht
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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December 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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