Sail into Luxury and Experience the Windy City Like Never Before

We work really hard to put the best product on the market. The reviews are in. Our clients LOVE us!

• We offer an exceptional inclusive service that strives to meet all you hearts desires.

• Generally speaking our Playpen Chicago experience starts around noon. We head out from the heart of the downtown Chicago harbor. 

• Water toys and floats, powerful high end 

• Stereo system developed by audio engineers

• Big spread, fruits, sandwiches, high noons, modelos, tequila, rum, aka you can have what ever you like

• We pull the anchor when the client says so, period. Generally around 5 o'clock.

We have a dynamic boat community you can join that serves you with a couple of options. We have worked to refine these products over the years.

1. For approved operators or aspirational operator we offer our yachts located at DuSable, Monroe, Belmont, and Montrose. Once your approved as a skipper you're able to captain our fleet. You also can tag along with frequent open sailing events as well as our Wednesday night racing program.

2. Social member - New product as of 2024. This package is designed for a individual or couple that wants to tag along with frequent opportunities to sail within our community. With this membership you also get an event on Guppy with friends and family.