A private sail for proposals, photos, and a champagne toast
2 hrs
Up to 12 people
Captain, snacks and beverages
Set sail along the Chicago Lakefront for a proposal or engagement photo session with city views from the water. Enjoy private time together aboard a 37-foot luxury sailboat.
Full refund 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: GCDMM2
Yes. Have every guest in your party sign the waiver for the engagement cruise.
Yes. You may bring your own food and beverages, including beer, wine, champagne, and hard seltzer.
Bring a rain jacket or layers for cooler days. Wear boat shoes, sandals, or tennis shoes with non-black soles.
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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