THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Leave the bustle of Navy Pier for two hours on a private sailboat and watch Chicago’s skyline redraw itself from the water. This flexible charter—operated by a USCG-licensed captain—lets you choose photos, sunset, or relaxed cruising with local stories on request.
Leave the bustle of Navy Pier for two hours on a private sailboat and watch Chicago’s skyline redraw itself from the water. This flexible charter—operated by a USCG-licensed captain—lets you choose photos, sunset, or relaxed cruising with local stories on request.
Verified experiences and guided adventures in the surrounding area.
Operated by Come Sailing, Inc. · Chicago, Illinois
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
easy.
2 hours.
Suitable for all fitness levels; requires basic mobility for boarding a marina dock and climbing a few steps on deck.
Yes; reasonable amounts of alcohol permitted in line with Illinois law—no glass containers and consume responsibly.
The captain may cancel for safety; charters are rescheduled when possible or refunded per the 24‑hour cancellation policy.
Accessibility varies by vessel; notify the operator when booking to confirm boarding options and any assistance needed.
Yes—this private charter is flexible. Tell the captain your preferences and they will adjust the route based on wind and safety.
Navy Pier opened in 1916 and has served as a military embarkation point, transit hub, and public entertainment venue, shaping Chicago’s lakefront development.
Lake Michigan faces runoff and invasive species challenges; follow captain guidance on waste removal and avoid throwing anything overboard to protect water quality.
Come Sailing, Inc. operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Come Sailing, Inc.
Book directly with Come Sailing, Inc. for the best rates and real-time scheduling.
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