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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$195-$940
Sailboats
Set sail with these traditional wind-powered boats
$125-$370
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$120-$800
Kayaks
Who says you need a motor to have fun on the water?
$50-$500
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$125-$180
Fishing Charters
Let a captain do the driving while you do the fishing
$75-$200
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$75
OP
Olivia
"Lake Mode" ON - 38' Four Winns
I was a bit nervous chartering because there weren't a lot of reviews. But I'm glad we did it. The boat is clean and comfy. The captain did a great job at making sure we were comfortable and taken care of. He was flexible and made us feel very welcome.
CB
CAMPBELL
Burnham Harbor, CAPTAIN/FUEL INCLUDED
Captain Joe and his deckhand Ryan were the absolute best!!! Captain Joe was safe and fun and got us a great spot in the playpen to anchor up. Ryan was so attentive and was always running around grabbing what we needed and refilling our drinks. We sat in the 6 seater float for a good portion of our time on the water and it was awesome. The boat is the perfect size for 7 people and has so much accommodation for all your bags in the bedroom underneath and they have a mini fridge in the bedroom as well as a large cooler on the back of the boat. We will 100% be rebooking through captain joe. He was amazing!!!
Christopher
27' Chris Craft with Water Toys plus Jet Ski Available
This was the perfect end to a long day for my family and me. Captain Tim was personable, attentive, and gracefully navigated a crowded waterfront for the 4th of July fireworks. The kids and I had a blast and enjoyed the relaxation. Would absolutely book again!
RJ
Rachel
Experience Lake Michigan like never before on Beautiful 35ft Maxum
Captain Savage was great at my friend’s bachelorette party! We wanted to do something fun and memorable in Chicago, and Capt Savage was very accommodating after a last-minute change in plans. He was friendly and the boat was clean. Perfect outing for a small group wanting to relax on Lake Michigan :)
AR
Alejandra
BIG BOAT SMALL PRICE EVERYONE CAN ENJOY | 45FT Sea Ray 400 Express Cruiser
Thank you so much for the incredible experience! The boat was stunning. We felt safe and taken care of and just had the best time. Will definitely be booking again. Communication and itinerary were flawless.
ZJ
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
I booked with Kevin for my boyfriends birthday surprise and it was EVERYTHINGGGG !!! my boyfriend was soooo happy and our friends and us had SO MUCH FUN !! 1000000/10 would recommend !! This was the best first time experience EVER !! thank you thank you thank you for helping me make my boyfriends birthday so special and a core memory we’ll have forever 💙 !!
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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December 16, 2019
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