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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,000
Sailboats
Set sail with these traditional wind-powered boats
$125-$435
Fishing Charters
Let a captain do the driving while you do the fishing
$20-$200
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$395
Kayaks
Who says you need a motor to have fun on the water?
$15-$80
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$40-$100
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275-$750
KC
Kate
Explore the Mississippi River aboard our Vintage Cabin Cruiser!
Debi and Matt are a delight to work with! I had a sunset photoshoot engagement vision as I’m a photographer and needed a vintage boat. They were communicative, accommodating and overall great in helping me achieve this idea. They also have an adorable Airbnb campground with retro campers they let us shoot on as well!
JF
Jessica
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
VERY responsive and VERY kind and helping. We had a blast! Perfect weather! Thank you again. Hope to see you in the future! Our birthday was awesome celebrating it on the lake. Thank you again.
DR
Disha
Gorgeous 46' Sea Ray Luxury Yacht Located in The Heart of Chicago
We had amazing time in Kevin’s yacht. It was super clean and comfortable!
EZ
Elizabeth
40ft Formula 40 Performance Cruiser in Chicago
This boat was great for a small group to go out for a birthday! It was quite choppy out which made it hard to enjoy, but Captain Jack provided options and recommendations to mitigate the waves as much as possible and also brought us back to the harbor when a few were not feeling well. Next time, we are packing more motion sickness medicine! But overall, boat was as advertised and definitely fit all 12 people.
Dana
40ft Formula 40 Performance Cruiser in Chicago
Everything was perfect! Captain jack was very sweet and had a great sense of humor. He was very accommodating to our group. Everything went really well and the group said they had a lot of fun. Would definitely recommend and will hopefully book again with Grace and Captain jack again :) thank you very much!
Carly
40ft Formula 40 Performance Cruiser in Chicago
This was hands down the easiest way to coordinate such a fun boat day. Grace answered every one of my questions almost immediately and was so helpful during the booking and coordinating process. Captain Jack was so skilled and friendly and we all felt safe with him behind the wheel. The photos are absolutely accurate and the boat is beautiful. I would recommend this boat to anyone looking for a great experience with their friends!
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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August 24, 2023
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May 03, 2023
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October 11, 2021
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March 27, 2020
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August 01, 2023
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