1. Why it matters—safety, money and jail time

The Coast Guard’s 2025 pre‑season bulletin lists fines of up to $49,848 for carrying even six passengers without a licensed captain, $14,988 for operating without the required Certificate of Inspection (COI) when more than six passengers are carried, and $9,624 for skipping the mandatory drug‑testing program for crew(news.uscg.mil). Violating a Captain of the Port Order—a common outcome after an illegal voyage is “terminated”—is a federal felony that can land an operator in prison, as the 2023 Playpen case demonstrated. Passengers are not immune; anyone who knowingly gives false statements during a boarding can also face fines or prosecution(workboat.com).

2. What makes a charter legal?

*State rules (IDNR), Chicago Park District harbor permits, and insurance terms layer on additional obligations.

3. Ten universal red flags

1. Head‑count math doesn’t add up – More than six guests aboard a recreational 30–45 ft express cruiser and no COI posted? Likely illegal.

2. Captain can’t produce a Merchant Mariner Credential (MMC) – The plastic, passport‑style license should be available on request.

3. No visible COI – Inspected vessels must display the certificate near the gangway; “I left it at home” is not an option.

4. Payment is routed through Venmo as “fuel split” or “donation.” Consideration in any form triggers the charter rules; clever wording does not erase liability.

5. No formal safety briefing – Legit captains point out life‑jackets, EPIRBs and fire‑extinguishers before leaving the dock.

6. Insufficient life‑saving gear – Count Type I or II life‑jackets for every person, plus throwable ring buoy; a pile of faded ski vests is not compliant.

7. Crew is partying with guests – A captain drinking alcohol while underway is a straight‑line safety violation.

8. Jet‑ski water‑taxi runs – Ferrying guests from shore to a moored boat for a fee still counts as “passenger for hire” and requires the same credentials.

9. Multiple back‑to‑back trips – Recreational owners rarely run four “friend” cruises a day. Commercial frequency is an enforcement clue.

10. No advertising trail – Paradoxically, many illegal operators do advertise—but only on closed Instagram stories or private WhatsApp threads. Lack of a public footprint can be as telling as an over‑aggressive one.

4. Playpen‑specific clues

• Improvised boarding ladders at the seawall. Legal charters embark from licensed Chicago Harbors slips; picking up passengers on the fuel dock or the Ohio Street seawall is a common shortcut.

• Rapid anchor resets. Because the Playpen is a no‑wake enclave, legal boats usually anchor once and stay put. Frequent weigh‑anchor cycles can indicate quick turnover trips.

• Boats rafting beyond three‐wide without fenders or lines. Overcrowded rafts are often the handiwork of unmanaged, for‑hire gatherings.

• Ignored hail on VHF 16. The Coast Guard and CPD Marine Unit routinely call suspected charters. No radio (or radio discipline) equals more risk.

5. How to verify legitimacy before you book

1. Use the Coast Guard’s “Research Before Renting” quiz. Developed in Chicago, the mobile tool walks you through a few questions and identifies red flags before money changes hands(mycg.uscg.mil).

2. Ask for the captain’s license number up front. Cross‑check against the National Maritime Center database or simply request a photo of the credential.

3. Look for a Chicago Harbors commercial permit decal. Legitimate local operators carry separate harbor stickers indicating they meet city rules.

4. Request the Certificate of Inspection if your group is larger than six. Operators who hesitate likely do not have one.

5. Confirm insurance. A true commercial marine policy (P&I plus “passenger for hire”) will be explicitly stated; most recreational policies exclude it.

6. What to do if you suspect an illegal charter

• Politely exit. If you have not departed, refuse to board and request a refund.

• Collect evidence. Photos of the boat name, HIN on the transom, or payment receipts help investigators.

• Report discreetly. Email SMBMSUChicagoInvest@uscg.mil or call (630) 986‑2155—the dedicated Investigations Division line—and provide what you observed. If you are already on the water, hail “Coast Guard” on VHF 16.

• Stay honest. Lying to law enforcement officers—e.g., claiming to be “friends” with the captain when you paid online—can make you a target of the investigation(workboat.com).

7. The bigger picture—supporting a safer Playpen

Illegal charters undercut the professional captains and crews who invest in training, safety gear, inspections and permits. They also tarnish the Playpen’s hard‑won image after the high‑profile accidents of 2021‑22 that spurred the current safety push. The more passengers choose licensed operations—and refuse shady offers—the faster the rogue market dries up.

8. Key take‑aways

• Six passengers is the magic number. More than six almost always means the boat must be Coast‑Guard‑inspected.

• No license on the wall? No go. The captain’s MMC and, when required, the vessel’s COI should be proudly displayed.

• Cheap rides are rarely safe rides. Below‑market rates usually signal missing paperwork or insurance.

• Use “Research Before Renting.” It’s free, takes minutes, and could save you a ruined day—or worse.

By keeping these points top‑of‑mind, you’ll not only protect your group’s fun but also contribute to a culture of responsible boating that lets Chicago’s one‑of‑a‑kind Playpen thrive for seasons to come. See you on the water—legally.