Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water
1+ hrs
Boat charter, Playpen anchorage
Set out for Chicago’s Playpen, where boats gather and the North Side skyline frames your time on the water. Anchor at the hotspot to swim, relax, and enjoy the atmosphere at your own pace.
Refundable with at least five days' notice. Cancellations less than five days before service incur a $150 fee.
Product ID: QZ5KCT
No. The boat and pier are not wheelchair accessible.
Bring your own meals and drinks for the Chicago Playpen charter.
C-Dock, Diversey Harbor, 2759 North Lake Shore Drive W, Chicago, IL 60614
Captain Bob has earned a near-perfect reputation on Lake Michigan, and it's easy to see why. Reviewers consistently praise his deep knowledge of Chicago's waterways, his engaging storytelling, and the relaxed, welcoming atmosphere he creates on board. His boat is frequently described as spotless, comfortable, and impressively well-maintained, with one guest comparing it to "a Porsche on water." What stands out beyond the boat itself is how personally invested Captain Bob seems in every outing. He tailors experiences to his guests, whether that means finding the best spots for the Air and Water Show or navigating to scenic sunset views. He's praised for being safety-conscious and skilled on busy waters, which clearly puts first-timers at ease. Repeat bookings and "can't wait to go back" comments show up throughout the reviews, which is about as strong an endorsement as you can get.
My wife and I had the pleasure of being on Captain’s Bob charter last weekend for the sunset cruise for our first anniversary. It was an awesome ride, full of fun and we even got to jam out to your own music. Captain Bob was very professional and gave an informative tour of the lake during the experience. Overall I would recommend this charter to whoever is looking for a great time on Lake Michigan. Thanks again Captain Bob
Anthony Sanchez-Ayra
July 13, 2026
My wife and I had the pleasure of being on Captain’s Bob charter last weekend for the sunset cruise for our first anniversary. It was an awesome ride, full of fun and we even got to jam out to your own music. Captain Bob was very professional and gave an informative tour of the lake during the experience. Overall I would recommend this charter to whoever is looking for a great time on Lake Michigan. Thanks again Captain Bob
Anthony Sanchez-Ayra
July 13, 2026
Cruise Chicago’s lakefront for skyline and Navy Pier views
Cruise about two miles offshore for wide-open Chicago sunset views
Speed across Lake Michigan with your own music and skyline views
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