About This Tour
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Photo Gallery
Relaxing on the bow with friends.
From the bow. Plenty of room on the foredeck for relaxing with friends and family.
Our sailboat, Bernard, sailing at sunset.
Sitting on the foredeck taking in a relaxing sail.
The Chicago Light. A great subject for your photos.
Four Mile Crib. Come Sailing and see a bit of Chicago history.
TopTours Insights
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
This private sailing trip on Lake Michigan offers a serene escape with a focus on the Chicago skyline. You'll spend two hours on a sailboat with a captain, enjoying the open water and gentle breezes. It's ideal for couples or small groups seeking a peaceful, scenic experience away from crowds.
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What's Included
What's Not Included
Additional Information
Meeting Point
We operate from the new Navy Pier Marina located along the north side of Navy Pier. Please gather outside of Navy Pier Marina - Gate D and then text/call us to tell us that you are here. We will welcome you to the marina and escort you to the sailboat.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
✓ Free cancellation due to bad weather
Tour Operator
Come Sailing, Inc.
Official supplier for this experience. Bookings are handled directly through Viator with verified partners.
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Guest Ratings
Total review count and overall rating based on Viator and Tripadvisor reviews
Based on 70 verified reviews
Average rating
Frequently Asked Questions
Common questions about Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
Who operates this experience?
This experience is operated by Come Sailing, Inc., a local sightseeing provider in Illinois.
What's included?
This tour includes Use of Bluetooth speakers, Navy Pier Facility Fee, and All taxes. Additional amenities and services are included. All inclusions are provided by the tour operator.
How long is this tour?
The experience lasts approximately 2 hours, giving you time to fully enjoy your chosen activity.
Can I cancel this tour?
Yes, you can cancel up to 24 hours before the scheduled departure time for a full refund. If weather conditions are unsafe, the tour may be canceled by the operator. In such cases, you'll be offered a refund or reschedule.
What should I bring?
We recommend bringing comfortable walking shoes, a camera, and weather-appropriate clothing. All necessary equipment is provided.
Will I receive instant confirmation?
Yes, you'll receive instant confirmation when you book.
Is this tour worth it?
Yes, this experience has a 5.0-star rating based on 70+ reviews, making it a highly rated option in Illinois.
What to expect on this tour?
This sightseeing experience lasts approximately 2 hours and includes all necessary equipment and guidance. You'll have access to Use of Bluetooth speakers and more.
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Book Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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