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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$330-$2,485
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 Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$130-$250
Fishing Charters
Let a captain do the driving while you do the fishing
$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.
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.
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!
MW
Michael
North River Sailing - See NYC from a Classic Racing Yacht
RENT THIS BOAT!!! The captain was incredibly generous, kind, accommodating and experienced. The boat was amazing. Will being going back again soon!
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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