Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
2.5 hrs
Up to 12 people
Captain, yacht, snacks
Sail the Chicago lakefront as the sun sets and take in skyline views from the water aboard a private 37-foot yacht.
Cancel up to 2 weeks before departure for a full refund, or up to 48 hours before for a 50% refund. Full refunds for lightning or high-wind weather cancellations are at the operator's discretion.
Product ID: K3F7B4
Yes. Every guest in your party must sign a waiver before the cruise.
Bring a rain jacket or layers for cooler days. Wear boat shoes, sandals, or tennis shoes with non-black soles.
Yes. Bring your own food and beverages, including beer, wine, champagne, or hard seltzer, for your sunset sailing cruise.
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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