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.
Private yacht charters · Chicago · Lincoln Square
Lake Michigan sailing charters built for Lincoln Square guests
Cast off from Montrose Harbor with USCG-licensed captains, skyline-first routing, and hospitality that stays steady when the lake kicks up. Sunset sails, Playpen afternoons, Navy Pier fireworks nights, and raft-up energy—whether your crew lives in Lincoln Square or you're hosting them for one Chicago weekend.
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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.
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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.