30 Spots Available

The Founding Fleet

Be one of 30 boats that launch Playpen Chicago. Founding Fleet is a recognition and advisory program, not a fee waiver.

Founding Fleet Benefits

Permanent "Founding Fleet" Badge

Your listing carries a distinctive Founding Fleet badge, signaling early-mover credibility and Chicago-launch participation to renters.

Priority Onboarding and Support

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

Founding Fleet Advisory Board

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

Early Launch Cohort

Founding Fleet vessels are part of the first wave to go live on the platform when the Chicago marketplace opens.

Requirements

✓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

Program Guardrails

Full transparency on how the Founding Fleet program works.

●Cap at 30 boats — once filled, the program closes
●Founding Fleet is a recognition and advisory program — it is not a fee waiver or commission discount
●Standard platform commission, application fee, and service fee apply to every booking, including Founding Fleet bookings, unless a separate written agreement signed by Playpen and the owner expressly states otherwise
●The Founding Fleet badge is permanent and signals the owner's participation in the launch cohort

Timeline

Now

Recruitment Open

Applications accepted on a rolling basis

Season 2026

Platform Launch

Founding Fleet vessels go live first

Apply for Founding Fleet

30 spots. Recognition badge, priority onboarding, and an advisory-board seat. Your chance to shape Chicago’s charter marketplace from day one.

Learn more about listing your boat