PRIVATE YACHT CHARTERS · CHICAGO, IL
Private Chicago sailing experiences
From skyline sunsets to high-energy Playpen days, explore Chicago by sail with a private captain and a seamless, premium experience designed for unforgettable moments.
Chicago sunset cruise
Experience a private sunset cruise on Lake Michigan with front-row views of the Chicago skyline. Perfect for date nights, proposals, and small groups, this charter is timed for golden hour and a smooth, relaxed ride.
Chicago fireworks cruise
Watch Navy Pier fireworks from your own private boat on Lake Michigan with front-row skyline views. Perfect for summer nights, celebrations, and small groups who want the show without the shoreline crowds.
Chicago Playpen charter
Anchor in Chicago's Playpen with a private charter built for swimming, music, and skyline energy—your captain handles safety and staging so your crew can relax and celebrate.
Our Chicago charter fleet
From premium private charters to hands-on sailing lessons, our fleet is built for unforgettable experiences on Lake Michigan—whether you're celebrating, cruising, or learning to sail.
Our flagship sailing yacht built for premium private charters. Spacious, smooth, and ideal for Chicago skyline sails, celebrations, and unforgettable group experiences on the water.
Our smaller private charter boat, perfect for intimate groups. Easygoing, flexible, and ideal for cruising the Chicago shoreline, date nights, and relaxed time on the water.
Designed for hands-on sailing lessons, Blue Moon is perfect for learning the fundamentals. Get on the helm, build confidence, and experience real sailing on Lake Michigan.
A seamless path from inquiry to cast-off—fewer clicks, more clarity.
Pick a charter window that fits your crew—we confirm tide and weather windows.
Brief safety and route; your sailing experience level shapes how hands-on we go.
Arrive at the dock with soft-soled shoes; we handle lines, ice, and the playlist.
