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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$75-$595
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$250
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$65-$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$250
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$210
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Natalia
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was awesome, super communicative, friendly, and made sure we were taken care of. There was a change to our departure time and a delay afterward, but he kept us well informed throughout. Captain Justin and his deckhand were fantastic hosts, making the experience fun and relaxing. We celebrated my husband’s birthday and had an absolute blast, even with the chilly May weather in Chicago. Overall, a great experience and highly recommend!
S
Sandra
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.
SR
Spencer
Cruise with the Best Captain on Lake Minnetonka!
We had an AMAZING afternoon on the lake. Dan was excellent with communication—quick to reply and easy going with our requests. The boat was perfect. Our group had a blast wake surfing and enjoying the views. Phenomenal experience all around!
J
Jeff
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.
CC
Colin
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
Amazing experience from start to finish. Group of 12 had an amazing time. Highly recommend and will definitely be booking again.
CF
Cooper
44' Italian Luxury Azimut Premier Party Yacht up to 13 plus Jet Ski Available
Capt. Tim & his son were awesome - very easy to work with and let us do our thing hanging out at the same 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!