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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,000
Kayaks
Who says you need a motor to have fun on the water?
$5-$270
Fishing Charters
Let a captain do the driving while you do the fishing
$5-$195
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$800
Sailboats
Set sail with these traditional wind-powered boats
$120-$370
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$395
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$5-$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
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!
Tay
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
I swear, if I could give 10 stars, I would! :-)My cousins and I had a remarkable experience on our family outing! Kevin is super professional and ensured our boat day went smoothly, we had some rough weather conditions on our initial date, but thankfully Kevin was able to switch us out for the next day—Very accommodating of him and we were truly grateful for that. Don’t hesitate to book his boat. Oh and I can’t forget the best captain ever, Jimmy! 😎 He’s amazing, super fun/chill and knows the all best spots to take great pictures. 11 out of 10 recommend! 👌🏾
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 💙 !!
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 :)
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!