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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$200
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90
Kayaks
Who says you need a motor to have fun on the water?
$225
Fishing Charters
Let a captain do the driving while you do the fishing
$90
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$225
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$300
CP
Chrystal
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
This was an Amazing event. The 46 ft Sea Ray was everything and more. From the Bow to the Stern, five ***** accommodations. Touring on the Chicago Lake against the Chicago Skyline, the scenery was breathtaking, the food was on point, and the bottomless mimosas had us feeling like we were vacationing on the French Riviera. IF you're looking for more than a boat ride, but an experience, book it. As you can see from the photos, this was indeed the ultimate Surprise Birthday Celebration, with a vibe. THANKS to the Owner, Kevin, for making this possible, and to Captain Justin for holding strong to that steering wheel.
DC
Daniela
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.
Emily
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Captain Tim was amazing! He was super communicative, fun, patient, and just a great captain overall. Everybody had a great experience on the boat and absolutely loved it! The boat itself was also gorgeous. We would definitely book with Captain Tim again.
cf
carolynn
Sail & Swim from a Luxury Sailing Yacht
This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)
DC
Derek
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Martin and his vessel were very well kept. The list of captains provided were very professional and polite. Martin was very prompt with communication and worked with each change needed through the process of scheduling the trip. I would very much so recommend him and his services. The trip was a success and enjoyable
Dapo
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Booking with Kevin was easy and convenient, providing a great experience. Captain Zach was amazing. If you have any doubts, just book the boat—you'll have an incredible time on the water like we did. I'll definitely book again.
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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May 20, 2021
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December 30, 2019
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December 26, 2019
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