Captain Trooper Moores

Step aboard with Captain Trooper for the ultimate Playpen party or Chicago River cruise, where fun, safety, and seamless vibes are guaranteed. Whether dropping anchor at the Playpen for a floating day party or cruising the Chicago River with skyline views, every trip is designed for a stress-free, unforgettable experience. Captain Trooper handles all navigation, docking, and logistics, letting you focus entirely on enjoying the music, drinks, and company. Each charter is fully customizable, whether you want a lively party atmosphere, a relaxing scenic cruise, or a mix of both. With expert knowledge of the waters and prime anchoring spots, guests can relax knowing they are in capable hands while making memories on Lake Michigan.

Guests are encouraged to bring their own food, drinks, and water toys to make the experience truly personal. Essentials like swimsuits, towels, sunscreen, and sunglasses help ensure comfort, while optional items like motion sickness pills and a change of clothes can enhance the day. Every detail is considered to create a safe, fun, and Instagram-worthy adventure, whether lounging on the deck, swimming, or exploring Chicago’s iconic riverfront. Captain Trooper guarantees smooth sailing, top-tier vibes, and a fully tailored charter for family, friends, or private events.