THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Step aboard a private two-hour sunset sail from Navy Pier and watch Chicago’s skyline transition as Lake Michigan’s breeze guides you past iconic landmarks. A flexible, captain-led cruise that’s equal parts skyline viewing and relaxed social time.
Step aboard a private two-hour sunset sail from Navy Pier and watch Chicago’s skyline transition as Lake Michigan’s breeze guides you past iconic landmarks. A flexible, captain-led cruise that’s equal parts skyline viewing and relaxed social time.
Book with Come Sailing, Inc.
Book directly with Come Sailing, Inc. for the best rates and real-time scheduling.
Reserve NowVerified experiences and guided adventures in the surrounding area.
Operated by Come Sailing, Inc. · Chicago, Illinois
The sailboat slips off its cleats at Navy Pier and the city exhales behind you: glass towers catch the last gold of the day while a cool Lake Michigan breeze pushes the bow forward.
easy.
2 hours.
Suitable for all fitness levels; participants should be able to board a small sailboat and stand or sit on deck for the duration.
This private two-hour charter accommodates up to six guests per booking.
Yes—reasonable amounts of alcohol are allowed within Illinois law and food may be consumed on deck; glass containers are prohibited.
The captain may cancel or reschedule for safety due to weather or mechanical issues; refunds are offered if rescheduling isn’t possible.
Boarding requires stepping aboard from the marina; notify the operator in advance about mobility needs so they can advise on feasibility and assist where possible.
Navy Pier opened in 1916 and has evolved from a shipping and military hub to a civic promenade; the lakefront also showcases projects from the City Beautiful movement and 20th-century urban planning.
Keep all trash off the water and avoid discarding food or plastics; charters follow no-discharge rules and local efforts focus on improving Lake Michigan’s water quality and habitat protection.
Come Sailing, Inc. operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Come Sailing, Inc.
Book directly with Come Sailing, Inc. for the best rates and real-time scheduling.
Reserve Now