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.
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.
Verified 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.
On a two-hour private charter you trade the thrum of the lakefront for a quieter rhythm—the water daring you to look up from your phone. The captain, USCG-licensed, will point out the skyline’s engineering feats, from the original colonnades of Soldier Field to the dome of the Adler Planetarium, while you steer the conversation or simply watch the light change on the skyscrapers.
Chicago’s lakefront is a product of glacial geology and deliberate urban planning. Navy Pier opened in 1916 and has shifted from shipping and military uses to the public promenade it is today; from the water you see both the city’s industrial past and its civic landmarks like Buckingham Fountain and the Museum Campus.
Expect flexible routing—wind and weather decide much of the course—and a private experience tailored to your group. Practicalities: charters are non-smoking, no glass containers, and alcohol is allowed within state law. Bring a wind layer, non-slip shoes, and a motion-sickness plan if you’re prone to it. Arrive early for check-in at the Marina; late arrivals can shorten your time.
This is not a deep historical lecture but a paced, sensory way to experience Chicago: the city presenting itself from a watery angle, the lake nudging you to notice details you miss from land. For photographers, skyline silhouettes and the glow after sunset are the payoff; for groups, the privacy and flexibility make it an easy, memorable outing.
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.
Come Sailing, Inc. operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
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.
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.
On a two-hour private charter you trade the thrum of the lakefront for a quieter rhythm—the water daring you to look up from your phone. The captain, USCG-licensed, will point out the skyline’s engineering feats, from the original colonnades of Soldier Field to the dome of the Adler Planetarium, while you steer the conversation or simply watch the light change on the skyscrapers.
Chicago’s lakefront is a product of glacial geology and deliberate urban planning. Navy Pier opened in 1916 and has shifted from shipping and military uses to the public promenade it is today; from the water you see both the city’s industrial past and its civic landmarks like Buckingham Fountain and the Museum Campus.
Expect flexible routing—wind and weather decide much of the course—and a private experience tailored to your group. Practicalities: charters are non-smoking, no glass containers, and alcohol is allowed within state law. Bring a wind layer, non-slip shoes, and a motion-sickness plan if you’re prone to it. Arrive early for check-in at the Marina; late arrivals can shorten your time.
This is not a deep historical lecture but a paced, sensory way to experience Chicago: the city presenting itself from a watery angle, the lake nudging you to notice details you miss from land. For photographers, skyline silhouettes and the glow after sunset are the payoff; for groups, the privacy and flexibility make it an easy, memorable outing.