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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$115-$1,875
Sailboats
Set sail with these traditional wind-powered boats
$65-$1,060
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$600
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$955
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$560
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$735
Kayaks
Who says you need a motor to have fun on the water?
$15-$400
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$310
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$15-$250
Canoes
A classic option for leisurely paddling
$15-$140
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$185-$460
Diving
Explore the ocean depths with trained boat operators
$85
Rafting
A high-energy adventure for the whole family
$65
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.
GT
Gabby
A Tropical Experience on a Massive Sailing Trimaran
David was an awesome captain and made my best friend’s bachelorette so much fun! He was the best captain and I definitely recommend him! His boat is so big and perfect for floating around!
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.
AV
Anna
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Brian and Erin were both amazing. We had the best afternoon on their boat. Highly reccomend!
EC
Eirum
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Captain Brian was the best! We sailed around Shelter Island, had a great swim, and enjoyed every minute on the boat! Perfect trip thanks to his great skills and warm personality!
BB
Barbara
A Tropical Experience on a Massive Sailing Trimaran
David was a most excellent captain. We were having a special send off for someone extremely important to us and David went above and beyond to make sure we all had a great time. He even got out his accordion and sang a song for the woman of the evening which was very funny and very special. We will absolutely book again. Thanks David and Sara!
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!
October 09, 2023
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December 30, 2019
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December 29, 2019
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December 26, 2019
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