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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$160-$915
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$600
Sailboats
Set sail with these traditional wind-powered boats
$90-$360
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$995
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$20-$1,050
Kayaks
Who says you need a motor to have fun on the water?
$10-$425
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$375
Canoes
A classic option for leisurely paddling
$10-$25
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$130-$195
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
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!
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!
Michael
42ft Searay Sundancer | LABOR DAY SPECIAL | Big Boat Small Price
Anthony and his wife were awesome. Boat was really clean and nice as described. Anthony is very knowledgeable of the river and lake and prioritized safety first. My friends and I enjoyed every minute of it.
NG
Norma
Stunning 45’ Sea Ray Yacht
Great experience all around! Everyone had such an amazing time!! A special thank you to Eugene for being so responsive. I highly recommend getting Captain Peter, he is so professional and really took care of us!
KP
Kavitha
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Excellent experience from start to finish - the boat was in good condition, clean and we had fun. Kevin was so easy to work with from start to end. Loved our time with family on the baot.
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!
April 17, 2024
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April 17, 2024
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December 30, 2019
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December 17, 2019
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August 01, 2023
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October 09, 2023
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