30 Spots Available

The Founding Fleet

Be one of 30 boats that launch Playpen Chicago.

Founding Fleet Benefits

Keep 100% of your charter revenue on your first 3 completed bookings. No time limit — go at your own pace.

Your listing carries a distinctive Founding Fleet badge forever, signaling trust and early-mover credibility to renters.

Dedicated onboarding specialist and priority access to our support team throughout the program and beyond.

Direct input on platform features, pricing tools, and marketplace policies through our Founding Fleet advisory board.

✓Active Chicago Harbors commercial departure permit (Bareboat/REC or UPV)

✓Verified commercial liability insurance ($1,000,000 minimum)

✓Minimum 8 professional photos of the vessel

✓Owner identity verification

✓Vessel in charter-ready condition

Full transparency on how the Founding Fleet program works.

●Cap at 30 boats — once filled, the program closes

●0% commission applies to your first 3 completed bookings per vessel — no time limit

●Standard marketplace commission (8-15%) applies automatically after 3 completed bookings

●Founding Fleet badge is permanent, even after the free booking period ends

Now

Recruitment Open

Applications accepted on a rolling basis

Season 2026

Platform Launch

Founding Fleet vessels go live first

30 spots. 0% commission on your first 3 charters. Your chance to shape Chicago’s charter marketplace from day one.