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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,135
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$900
Sailboats
Set sail with these traditional wind-powered boats
$125-$540
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$345
Kayaks
Who says you need a motor to have fun on the water?
$10-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$800
KF
Khari
Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
We had an amazing time out on the water thanks to boat owner Breanna and Captain Mike! From the moment we arrived, everything was handled professionally and with such a warm, welcoming attitude. Breanna made the booking process smooth and stress-free, and Captain Mike was outstanding—friendly, knowledgeable, and clearly experienced. What stood out the most was how safe we felt the entire time. Captain Mike explained all the safety protocols before we left the dock, and throughout the trip, he stayed attentive and in control. It allowed us to fully relax and enjoy the experience, knowing we were in great hands. The boat was clean, comfortable, and well-equipped. Whether you’re looking to cruise, swim, or just soak up the sun, this is the trip to book. We highly recommend Breanna and Captain Mike to anyone looking for a safe and unforgettable boating experience. We’ll definitely be back!
Husein
20' Lund Bass Boat for 3 in Chicago, Illinois
I honestly didn’t expect to walk away from this trip with a whole new hobby, but here I am—hooked for life. Guy has this way of making the entire experience feel effortless and exciting, whether you’re a total beginner or someone who’s been at it for years. From teaching the basics with real patience to creating an atmosphere that’s both laid-back and full of energy, he made it easy to fall in love with fishing. The way he explained the gear, read the water, and shared his stories made every moment out there on the water feel like something special. You can tell he truly loves what he does, and that kind of passion is contagious. I went in thinking this was just a one-time adventure, but now I’m already planning my next trip—and buying my own gear. Can’t thank Guy enough for turning what was supposed to be a relaxing weekend into the start of a lifelong obsession. If you’ve ever been on the fence about trying fishing, let Guy be the reason you dive in—you won’t regret it.
MH
Mary Bev
20' Lund Bass Boat for 3 in Chicago, Illinois
Thanks for a great day on the water, Capt. Guy! We had a phenomenal morning, and we hope to fish with you again soon! Great variety of salmon & steelhead. 10/10 recommend
TJ
Tisha
Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
10/10 experience !!!
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.
EB
Elizabeth
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
Earl was an absolute pleasure to work with- very flexible and gave us the chance to have the best day in his boat! The boat is large and spacious and we had a wonderful time
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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September 13, 2023
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