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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$80-$425
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$100-$1,395
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$35-$145
Fishing Charters
Let a captain do the driving while you do the fishing
$85-$180
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$90-$195
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$115-$200
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$195-$200
AD
Alejandro
Charter a 31' Pearson Cruising Sloop, Chicago
Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.
AC
Alicia
37' Luxury Sailing Yacht in Downtown Chicago
When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!
Alexander
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Such a great outing! We went for my girlfriend’s birthday and had the best time. Amazing boat, amazing captain, amazing dog! Could not have gone better.
RM
Raymond
37' Luxury Sailing Yacht in Downtown Chicago
Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!
Hitesh
Charter a 31' Pearson Cruising Sloop, Chicago
Captain Joey was great! Gave very clear directions on how best to meet up with him and is clearly an expert at what he does. Would highly recommend him!
JW
Jessica
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!
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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August 12, 2021
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December 30, 2019
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December 26, 2019
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