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 sailing charters · Lake Michigan · Uptown
Captained yachts on Lake Michigan — itineraries planned from Uptown
Choose your window; we manage lines, ice, sound, and safety. Every charter stages from Montrose Harbor with licensed crew, polished boats, and routes dialed for sunsets, fireworks corridors, and Playpen summer days—starting wherever your group gathers in Uptown.
← All charters
Private Chicago sailing experiences
Choose Your Perfect Day on the Water
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 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.
← Full fleet
Our Chicago charter fleet
Choose the Right Boat for Your Experience
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.
Vagabond
- Length
- 39ft
- Capacity
- 10 guests
- Price / 3 hrs
- STARTING AT $750
Beneteau Oceanis 393 sailing yacht for private Chicago charters—skyline views, sunset sails, Playpen days, and relaxed Lake Michigan cruising from Montrose Harbor.
Drifter
- Length
- 30ft
- Capacity
- 6 guests
- Price / 3 hrs
- STARTING AT $675
A relaxed, budget-friendly Chicago boat charter for small groups who want skyline views, date nights, and easy time on Lake Michigan.
Blue Moon
- Length
- 26
- Capacity
- 4 guests
- Price / 2 hrs
- STARTING AT $250
A beginner-friendly sailing lesson boat built for hands-on learning, first-timers, and students of all ages. Grade school, middle school, high school, and college students receive $50 off lessons.