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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$80-$1,115
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$60-$1,045
Sailboats
Set sail with these traditional wind-powered boats
$70-$1,120
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$65-$635
Kayaks
Who says you need a motor to have fun on the water?
$40-$855
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$1,300
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$80-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$90-$400
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$1,300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$100-$3,125
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$50-$425
Diving
Explore the ocean depths with trained boat operators
$500
SD
Shaunak
Chicago's Largest Chartered Catamaran!
Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!
Veronica
Chicago's Largest Chartered Catamaran!
My friends and I rented the catamaran boat from Jim for the 4th of July and had such an amazing time. The boat was even better in person and comfortably fit me and 12 of my friends. Captains Russell and Brian were also amazing. They were so much fun and so accommodating. They set everything up for us (the cooler with all of our drinks, bowls of chips we had brought, etc). We rented the boat for 3 hours but were having such a good time that we asked if we could pay to extend our use for another hour. Luckily they had no other immediate obligations and they were able to make it happen. As a nice bonus, they even had those fun water noodles for us to use. So much fun and my friends and I can't wait for our next boat outing with these guys!
NS
Nitya
Beautiful Trimaran for 10 People in Toronto
Chris and Rob are simply amazing ! They showed us the best time on the boat. They had all services available on board to heat food and store our stuff. The boat was clean, spacious and both, Chris and Rob, were very attentive to make sure we had everything we needed to enjoy our experience. I'm coming back to these guys each time i want a sailing experience ! Highly recommend these guys
JB
Janis
Beautiful Trimaran for 10 People in Toronto
Many thanks to Chris and Rob for an amazing, chill adventure. We had to book this last minute but they were very accommodating and even went above and beyond all expectations. My only regret was not booking this experience sooner with your boat and crew. Thanks again! All the best, JB
Emma
Beautiful Trimaran for 10 People in Toronto
We had a lovely evening on the catamaran with Captain Chris and the crew! I was a bit chaotic with organizing with Chris for confirming dates/times/number of people joining as it was for a bachelorette. Chris was extremely patient and accommodating throughout the whole experience. The boat was beautiful and we were taken to lovely locations for beautiful views. I have already recommended this experience to many people!
SS
Srijanani
Beautiful Trimaran for 10 People in Toronto
We had a great time with Chris and his crew. Really appreciated the relaxed and friendly approach and communication.The boat is big enough to hold 12 ppl comfortably. The hammock is a great way to relax and take in the views. Chris took us out to a warm calm swimming spot and provided floaties and pool noodles too! The views, chats with captain and crew all added to the wonderful experience. Bluetooth speaker is provided with the boat to enhance the vibe. Amazing time spent out on the water!!
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!