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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$115-$690
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$255
Sailboats
Set sail with these traditional wind-powered boats
$55-$1,065
Fishing Charters
Let a captain do the driving while you do the fishing
$110-$255
Kayaks
Who says you need a motor to have fun on the water?
$45-$330
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$15-$185
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$145-$255
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$185
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$110
SM
Sarah
Now 50% OFF 45 Foot Luxurious Yacht Charter
I threw a birthday party on a yacht, and it was honestly one of the best decisions ever! The vibe was perfect right from the start. The yacht was super sleek and spacious, with incredible views as we cruised around. Everyone was having such a great time that we decided to extend the party! Matt was awesome—super chill but made sure everything ran smoothly, so we could just focus on enjoying ourselves. We had great music, food, and drinks, and the whole atmosphere was just next level. Afterward, we headed to La Vecchia for dinner, which was the perfect way to wrap up the day. If you’re looking for an epic celebration, I can’t recommend Matt enough. It was definitely a day to remember!
Katie
Now 50% OFF 45 Foot Luxurious Yacht Charter
Matt was a fantastic captain who took us on a wonderful boat ride. The boat was beautiful and well-maintained, making our trip even more enjoyable. Matt's knowledge of the city and his warm hospitality made the experience truly memorable. Thank you so much we had a blast!!!
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. ☀️🛥️🌊
NO
Nwabueze
44' Luxury Double Decker in Toronto for any Occasion / Event
We had the most amazing experience, thanks to Jay. From the moment we booked until the end of our trip, he went above and beyond to ensure everything was perfect. The boat was immaculately clean, well-maintained, and stocked with thoughtful extras that made our time on the water even more special. His hospitality and attention to detail was outstanding—he provided helpful tips, customized our itinerary to match what we wanted, and were always available for questions or assistance, making us feel completely at ease. It’s rare to find someone who genuinely cares about making sure their guests have the best experience possible, but Jay truly does. I can't recommend him enough! If you’re looking for a first-class boating experience, this is the person to book with. We will definitely be back!
Segolame
Now 50% OFF 45 Foot Luxurious Yacht Charter
My friends and I had an absolutely fabulous time and I’m recommending this boat to everyone I know. The captains were exceptionally friendly, professional, and helpful, even offering us a complimentary drink. Despite our late arrival, they were very patient and gave us extra time. It was truly a wonderful experience. Don’t hesitate to book with Matt—he’s incredibly charming, thoughtful, and delightful
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.
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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December 26, 2019
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