Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
3 hrs
Up to 7 people
Captain, private sailboat, snacks
Sail Lake Michigan aboard a private 37-foot yacht and take in Chicago’s lakefront architecture from the water. Choose calm inshore cruising or more active offshore sailing, with time to relax on deck or swim.
Cancel up to 2 weeks before departure for a full refund, or up to 48 hours before for a 50% refund. Full refund if the operator cancels due to lightning or high wind.
Product ID: TVWCNM
Bring layers or a rain jacket for cooler days. Wear boat shoes, sandals, or tennis shoes with non-black soles. Pack a bathing suit if you plan to swim during the Chicago Lakefront Cruise.
Your sail may continue in passing rain, so dress accordingly. Departure delays, rescheduling, or rain checks may be available. The operator cancels for current or forecasted lightning or high wind.
Navy Pier Marina, 797 E. Grand Ave., Chicago, IL 60611
Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!
Jonathan Garcia
June 24, 2026
Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!
Jonathan Garcia
June 24, 2026
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