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Fishing Charters
Let a captain do the driving while you do the fishing
$90-$525
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$525
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$145
Kayaks
Who says you need a motor to have fun on the water?
$15
Sailboats
Set sail with these traditional wind-powered boats
$195
Adam
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Had an incredible time out on Kevin’s boat. We had Captain Justin and I couldn’t recommend him enough. We were celebrating a bachelor party and this was the highlight of the weekend!
MF
Maddie
Stunning 45’ Sea Ray Yacht
We rented out this yacht for my boyfriend’s birthday party! The boat was spacious and just as described. Our captain Peter and his wife were an amazing crew, thorough with safety, attentive, and went above and beyond to make sure that we had an incredible time! Booking with Eugene was a breeze, he was quick to respond, as well as answered every question that I asked! Everyone had a blast, and we will definitely be booking through them again!
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!
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!
August 01, 2023
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October 09, 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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