Chicago Sunset Sailing Charter
A golden-hour sail for date nights, anniversaries, proposals, and relaxed evenings on Lake Michigan. Watch the Chicago skyline shift into sunset from a private sailboat.
Chicago Private Boat Charters & Sailing Experiences
Chicago’s best momentsstart on the water
Private boat charters and sailing lessons on Lake Michigan—sunset cruises, fireworks nights, Playpen days, and hands-on experiences, all led by a licensed captain and tailored to your group.
Lake Michigan - Chicago
Sunset to Fireworks
Sunset sails timed for golden hour
Front-row views of Navy Pier fireworks
Built for Your Group
Private charters for small groups
USCG-licensed captain included
Explore Lake Michigan
Cruise the skyline, harbors, and Playpen
From casual sails to premium yacht experiences
Chicago Fireworks Sailing Cruise
A summer-night sailing experience built around Chicago fireworks, skyline views, and time on Lake Michigan. Ideal for birthdays, visitors, date nights, and memorable group outings.
Chicago Playpen Sailboat Charter
A social Lake Michigan boat day for birthdays, bachelorettes, friend groups, and summer celebrations. Cruise toward the Chicago Playpen for skyline views and a livelier lakefront atmosphere.
Chicago Lake Michigan Cruising Charter
An easygoing private lake cruise for guests who simply want to get on the water. Great for visitors, families, couples, and casual groups looking for Chicago skyline views without the party-boat feel.
Chicago Sailing Lessons
Chicago sailing lessons $250 / 2hrs on a 26' Chris-Craft on Lake Michigan—practical coaching: vocabulary, points of sail, rules of the road, tacking & jibing with a licensed captain.
Lake Michigan Scuba Trips
Explore Lake Michigan dive sites with guided, boat-supported scuba trips—pricing TBD. Perfect for certified divers looking for unique freshwater experiences.