Private Lake Michigan sailing with swimming, snacks, and a certified captain
4 hrs
Up to 12 people
Captain, snacks, beverages
Explore Lake Michigan on a private sailing yacht with time to swim, float, and relax on board. Enjoy captain-led sailing with amenities for a day on the water.
Full refund for cancellations up to 2 weeks before departure; 50% refund up to 48 hours before. Full refund if the operator cancels due to lightning or high wind.
Product ID: 7FU9EX
Bring a rain jacket or layers for cooler days, boat shoes, sandals, or non-black-soled tennis shoes, and a bathing suit if you plan to swim.
Yes. You may bring your own food and beverages, including beer, wine, champagne, and hard seltzers.
Yes. Every guest in your party must sign the participant waiver before departure.
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
Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
A private sail for proposals, photos, and a champagne toast
Cruise Chicago’s waterfront with a professional crew and private gathering spaces
Celebrate on the Gypsy Spirit along Chicago’s waterfront