Chicago Private Boat Charters on Lake Michigan
Private boat charters for small groups on Lake Michigan—sunset sails, fireworks nights, Playpen days, and sailing lessons, all led by licensed captains and tailored to your experience.
Curated Fleet
From premium sailboats to smaller group charters
Options for intimate, private groups
Lake Michigan Sailing
Chicago skyline, harbors, and Playpen
Direct access to top on-water destinations
Captain-Led Experience
USCG-licensed captains
Seamless, private charter experience
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.
