Book Online · 2026 Season Pick a date.
Pick a date.
Pick a boat. Set sail.
Browse live availability across our 22-yacht fleet, choose the right vessel for your group, and book instantly with secure checkout.
Live availability & Pricing
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Instant confirmation Secure checkout Best price guarantee
View all 22 yachts →Simple Process
How booking works
01
Pick your date
Choose from available dates and times. We're open seven days a week, April through October.
02
Select your boat
Browse the fleet and find the perfect vessel for your group — from 1 to 125 guests.
2.5
Hire a captain USCG regulations require a licensed captain for boats up to 13 passengers.
13-passenger boats only — captain hired separately at checkout.
03
Set sail
Meet your captain at the harbor and enjoy Lake Michigan, the skyline, and The Playpen.
Not sure which boat?
Explore the fleet first.
Compare amenities, capacities, and harbors across our collection of yachts before you book — then come back and lock in your date.
22Yachts
1–125Guest capacity
37′–78′Vessel lengths
Need help choosing?
Talk to a human.
Our team has been on the water in Chicago for a decade. Tell us the occasion and group size — we'll match you with the right boat same-day.
7 DAYS A WEEK · 9AM – 9PM CT