Captain with Playpen Chicago
Set your own rates. Choose your vessels. Build your reputation on Lake Michigan’s premium charter platform.
How It Works
Apply
Submit your USCG credentials, insurance, and experience.
Get Verified
Our compliance team verifies your MMC through the National Maritime Center.
Get Authorized
Vessel owners authorize you for specific boats after orientation.
Accept Gigs
Review and accept charter assignments that fit your schedule.
Get Paid
Receive your rate via Stripe after each completed charter.
Your Rates, Your Schedule
You set every rate. We take 0% of captain fees.
Configurable Rate Structure
- •Base hourly rate
- •Half-day flat rate (4 hours)
- •Full-day flat rate (8 hours)
- •Overtime hourly rate
- •Day of week: weekday vs. weekend vs. Friday premium
- •Occasion surcharge: premium for corporate events, weddings, holidays
- •Vessel class surcharge: 30–45 ft, 46–60 ft, 61+ ft
- •Time of day: early start surcharge, night surcharge
- •Holiday/event multiplier
- •Minimum booking duration
- •Blackout dates (dates you’re unavailable)
Your availability calendar is entirely yours. Block dates, set recurring availability, mark yourself unavailable for any reason.
No minimum hours required by the platform. Work as much or as little as you want.
Market Benchmarks
Source: Boatsetter data
| Boat Size | 4-Hour Rate | 8-Hour Rate |
|---|---|---|
| Under 30 ft | $200 | $350 |
| 30–49 ft | $240 | $425 |
| 50+ ft | $350 | $650 |
These are market benchmarks only. You set your own rates.
What You Need
USCG Merchant Mariner Credential (OUPV or Master)
OUPV (6-pack): authorizes up to 6 passengers for hire on uninspected vessels
Master: authorizes higher tonnage and may cover more passengers on COI vessels
Drug test compliance (per USCG regulations)
First Aid / CPR certification (current)
Captain’s professional liability insurance ($300,000–$500,000 minimum)
Naming both:
- The Playpen Enterprises LLC as Additional Insured
- The vessel owner as Additional Insured (added per vessel authorization)
Background check authorization
W-9 for tax reporting
Boat Authorization
You don’t captain every boat on the platform. You get authorized for specific vessels by their owners.
3-Layer Eligibility Filter
Credential Type
Your USCG credential must cover the vessel’s route and tonnage. OUPV captains are limited to 6 passengers on uninspected vessels.
Boat Authorization
The vessel owner must specifically authorize you after a vessel orientation. You can be authorized on multiple boats.
Availability
You must be available on the requested date and within duty hour limits.
Owners can maintain a preferred captain list. Renters see suggested captains but can request any qualified captain in the network.
For bareboat charters (Mode B2): the renter selects the captain. This is a USCG compliance requirement (NVIC 7-94), not a platform choice.
Getting Paid
on captain earnings
Playpen takes 0% of captain fees. Your rate is your earnings.
Payment flows through Stripe for record-keeping and compliance. The legal relationship is between you and the renter (for bareboat charters) or you and the operator (for captained charters).
Payout timeline:3–5 business days after trip completion.
Your dashboard shows: upcoming earnings, completed payouts, earnings by period, and tax summary.
Tax Obligations
You are an independent contractor, not an employee.
- •1099-NEC issued if annual earnings exceed $600
- •W-9 required during onboarding — gig assignments are blocked until W-9 is on file
- •You are responsible for your own income tax filings, estimated quarterly payments, and self-employment tax
Consult your tax advisor.
$500
Milestone Bonus After 10 Completed Charters
Per captain, across all vessels. Only completed charters count — cancellations, no-shows, and weather-aborted trips do not increment your counter.
Your dashboard tracks your progress: X of 10 charters toward your $500 milestone bonus.
Duty Limits and Safety
Safety is non-negotiable. You have final authority on all weather and departure decisions.
Duty Limits
Maximum daily charter hours (configurable, default 12 hours)
Minimum turnaround between trips (configurable, default 2 hours)
Maximum consecutive trip days (configurable, default 5)
Relief captain required for trips exceeding duty limits
The platform enforces these limits automatically. You cannot be assigned a gig that would violate your duty limits.
If you make a weather call to cancel, the renter receives a full refund or reschedule. Your rating is not penalized for weather cancellations.
Substitution Rules
If you can’t make an assigned charter, notify the platform as early as possible.
The platform activates a substitution search to find a qualified replacement captain.
Your rating is not penalized for cancellations with 48+ hours notice.
Cancellations with less than 48 hours notice may affect your reliability score.
Repeated short-notice cancellations may result in reduced visibility for new gig assignments.
Your Dashboard
- ✓Upcoming gigs (vessel, date, time, renter, guest count, your rate)
- ✓Earnings (by period, by vessel, tax-year summary)
- ✓Availability calendar (set recurring availability, block dates, blackout dates)
- ✓Credential alerts (MMC expiration, insurance renewal, CPR certification)
- ✓Authorized boats (which vessels you’re approved for, pending authorizations)
- ✓Charter history (completed trips, ratings received)
- ✓Milestone bonus tracker
Insurance Explained
Why You Need to Name Both the Platform and the Vessel Owner
Your captain’s liability insurance must name The Playpen Enterprises LLC as Additional Insured (platform protection) AND the vessel owner as Additional Insured (per vessel authorization). This is standard in the charter industry.
How to Get It
Contact your marine insurance provider. Request a Certificate of Insurance (COI) with both entities listed as Additional Insured. Add new vessel owners as you get authorized on additional boats.
Most insurers charge $50–$100 per Additional Insured endorsement.
Frequently Asked Questions
Ready to Join the Network?
Questions? Call (312) 776-3311 or email captains@chicago.theplaypen.com