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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$215-$1,750
Sailboats
Set sail with these traditional wind-powered boats
$185-$1,530
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$950
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$950
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$160-$780
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$75
FG
Fran
"RENT ME" Spacious 38' Cruiser- plenty of room for celebrating or relaxing!!!
Our family had an amazing time on the Kraken. Captain Ken was a gracious host and helped us to create a day that was just what we hoped for. The boat is beautiful and comfortable. We knew we were in the care of a knowledgeable and experienced captain. I would highly recommend Captain Ken and The Kraken. We are still smiling as we remember our day. ☀️🛥️🌊
TT
Todd
Spend the Day on Buzzards Bay - Aboard the classic Dyer 29 Classic Boat
The trip was perfect. Steve was great host, guide and captain. The communication was great, the boat was the perfect size for our group and the tour into the Bay was amazing. I can't wait to do it again when we're next on the island.
DM
Deneen Mazzone
"RENT ME" Spacious 38' Cruiser- plenty of room for celebrating or relaxing!!!
To Say our girls trip Saturday on the Kraken with our captain Ken Hammond was a good time is an understatement. Ken made this a very enjoyable and memorable day. We are already looking forward to booking a day with Ken again.
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.
JB
Jennifer
Henriques Motor Yacht for Dock, dine, cruise, explore in New Jersey!!
This was a work related outing for lunch and a cruise down the river - we viewed it as a nice opportunity to do some team building with our new associates. My Boys was perfect size vessel for the six of us and was spotlessly clean including the bathroom. The music, cocktails and great vibes made it an exceptional summer afternoon - we definitely will look to do this again next year.
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!
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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