Before You Head Out to the Playpen in Chicago — 10 Yacht-Day Musts

Fuel, pump-out, provisioning, weather gear, safety checks & permits—everything a Chicago Playpen boat rental…

Set Sail the Right Way: A Complete Playpen Chicago Guide for Renters & New Yacht Owners

Whether you’re a first-time renter or the proud owner of a shiny new cruiser,…

Spotting Illegal Charters in Chicago’s Playpen: A 2025 Boater’s Guide

Spotting Illegal Charters in Chicago’s Playpen: A 2025 Boater’s Guide Home Blog June 15,…

Boat Charter Licensing in Chicago

The Playpen Chicago Captain Network: Your Path to Earning Income on Lake Michigan as a USCG-Licensed Captain

If you’re a United States Coast Guard (USCG)-licensed captain looking to turn your maritime…

Navigating the Waves: A Comprehensive Look at the Chicago Boat Show January 8-12, 2025

Navigating the Waves: A Comprehensive Look at the Chicago Boat Show January 8-12, 2025…

Exploring the Chicago Harbor Lock: History, Functionality, and Its Impact on Waterway Travel

Exploring the Chicago Harbor Lock: History, Functionality, and Its Impact on Waterway Travel Home…

Chicago Celebrities Waterskiing at the Playpen—Yes, Even on Christmas Day!

Chicago Celebrities Waterskiing at the Playpen—Yes, Even on Christmas Day! Home Blog December 26,…

Exploring the Boating Scene in Chicago: Harbors, Yachts, Charters, and More

Exploring the Boating Scene in Chicago: Harbors, Yachts, Charters, and More Home Blog December…

Where Is the Playpen Chicago and What Is It? A Complete Guide to the Windy City’s Unique Boating Hotspot

Where Is the Playpen Chicago and What Is It? A Complete Guide to the…

Discovering Chicago’s Harbors for the Ultimate Yacht Charter Experience

Discovering Chicago’s Harbors for the Ultimate Yacht Charter Experience Home Blog December 14, 2024…

The Playpen in Chicago: Its History, Features, Boating Scene, and Controversy

The Playpen in Chicago: A Comprehensive Look at Its History, Features, Boating Scene, and…

The Playpen Chicago featured on Chicago’s Own WGN TV

The Playpen Chicago featured on Chicago’s Own WGN TV Home Blog December 10, 2024…

Spectacular Drone Show and Winter Festivities at Navy Pier

Spectacular Drone Show and Winter Festivities at Navy Pier Home Blog December 9, 2024…

Maximizing Fun, Minimizing Risk: Understanding Passenger vs. Crew Limits on Bareboat Charters in Chicago’s Playpen

Maximizing Fun, Minimizing Risk: Understanding Passenger vs. Crew Limits on Bareboat Charters in Chicago’s…

Is It Safe to Jump Off a Boat, Swim, or Use a Lily Pad at the Playpen in Chicago? A Comprehensive Guide

What are the factors that influence safety at the Playpen, including water conditions, weather,…

How to Find and Hire a Captain for Your Boat Charter at the Playpen in Chicago on Lake Michigan

We’ll break down what a bareboat charter is, why captains are hired separately, how…

How to Charter a Boat at the Playpen in Chicago on Lake Michigan: A Complete Guide

From choosing the right charter company and budgeting tips to what to bring and…