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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$125-$1,745
Sailboats
Set sail with these traditional wind-powered boats
$100-$1,070
Fishing Charters
Let a captain do the driving while you do the fishing
$40-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$55-$575
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$55-$765
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$360
Kayaks
Who says you need a motor to have fun on the water?
$10-$365
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$40-$250
Diving
Explore the ocean depths with trained boat operators
$85
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$175-$460
Canoes
A classic option for leisurely paddling
$15-$30
Rafting
A high-energy adventure for the whole family
$65
AH
Alaina
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
If you're contemplating any other boat for reasons aside from capacity, don't look any further. Matt is your guy. The whole party showed up at varying times, he let us get going on the boat to get the vibes started. He was such a great host. We felt extremely welcome. He definitely upped the vibe of the whole party. I'm so glad I chose him to host us. I would 100% recommend him to anyone I know looking to book a boat and I'll certainly book with him again myself when the opportunity arises again. 11/10!
Salara
44' Luxury Double Decker in Toronto for any Occasion / Event
Booked a trip for my birthday in august. We had a great time, Jay was an excellent caption and we have no complaints at all. Would definitely book again and would recommend him to anybody looking for a special and fun way to celebrate any event
Marijka
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
We took a sunset boat ride with Matt to celebrate my 25th birthday. Our experience was absolutely wonderful and surpassed all of our expectations! Matt was so friendly and accommodating taking us downtown to look at the Toronto skyline, blasting karaoke and partying in the rain. Thank you for making my 25th such a memorable night Matt!
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!
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.
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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