Sail Lake Michigan privately with skyline views and a captain
3 hrs
Up to 7 people
Captain, yacht, snacks
Set sail from Navy Pier Marina on a private 3-hour cruise along Chicago’s lakefront. Take the helm, swim, or relax on deck with a USCG-certified captain.
Full refund up to two weeks before departure; 50% refund up to 48 hours before departure. Full refund if the operator cancels due to lightning or high wind.
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