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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$270-$465
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$300
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$300
Sailboats
Set sail with these traditional wind-powered boats
$75-$150
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$300
Katie
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!!!
SK
Sai
27' Chris Craft with Water Toys plus Jet Ski Available
Our experience with Captain Tim Jr was incredible! He is a fantastic captain, the boat was awesome, and he battled a storm to get us to the fountain, I proposed to my girlfriend, and he battled the storm right back to the dock. An experience we will never forget, best captain you could ask for!
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
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
Tay
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
I swear, if I could give 10 stars, I would! :-)My cousins and I had a remarkable experience on our family outing! Kevin is super professional and ensured our boat day went smoothly, we had some rough weather conditions on our initial date, but thankfully Kevin was able to switch us out for the next day—Very accommodating of him and we were truly grateful for that. Don’t hesitate to book his boat. Oh and I can’t forget the best captain ever, Jimmy! 😎 He’s amazing, super fun/chill and knows the all best spots to take great pictures. 11 out of 10 recommend! 👌🏾
WS
William
Stunning 45’ Sea Ray Yacht
The boat was fantastic. The crew was nice, helpful, knowledgeable, and created an awesome afternoon for our group. We had a great time on the water and it was a great day for a group visiting Chicago. Great day!
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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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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