THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Leave the bustle of Navy Pier for two hours on a private sailboat and watch Chicago’s skyline redraw itself from the water. This flexible charter—operated by a USCG-licensed captain—lets you choose photos, sunset, or relaxed cruising with local stories on request.
Leave the bustle of Navy Pier for two hours on a private sailboat and watch Chicago’s skyline redraw itself from the water. This flexible charter—operated by a USCG-licensed captain—lets you choose photos, sunset, or relaxed cruising with local stories on request.
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
Verified experiences and guided adventures in the surrounding area.
Operated by Come Sailing, Inc. · Chicago, Illinois
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
From the deck a US Coast Guard–licensed captain trims the sails, and the city becomes a moving map: the domed silhouette of Adler Planetarium, the colonnades of Soldier Field, and the vertical rhythm of the Loop. Lake Michigan has its own personality here — a wide, cool current that nudges the bow and lifts the view.
Chicago’s lakefront grew from reclaimed shoreline and industrial piers into public space over the 20th century; Navy Pier opened in 1916 and long served military, commercial, and entertainment roles. Geologically, the lake sits on glacial scours carved at the end of the last ice age; that depth gives the water a steady, sometimes brisk motion and clear sightlines back to the city.
This private two-hour charter is flexible: ask to circle major landmarks, chase sunset light, or drift for skyline photos. The captain will offer historical anecdotes on request but this isn’t a walking tour — it’s a maritime experience built around your group.
Practical notes: expect light spray and cooler temperatures on-deck even on warm days, bring layered clothes, non-slip shoes, and sun protection. Boarding begins at the Navy Pier Marina; arrivals late may shorten your sail. The captain controls route and safety decisions; weather will dictate whether a sail proceeds or is rescheduled.
Yes; reasonable amounts of alcohol permitted in line with Illinois law—no glass containers and consume responsibly.
The captain may cancel for safety; charters are rescheduled when possible or refunded per the 24‑hour cancellation policy.
Accessibility varies by vessel; notify the operator when booking to confirm boarding options and any assistance needed.
Yes—this private charter is flexible. Tell the captain your preferences and they will adjust the route based on wind and safety.
Come Sailing, Inc. operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
From the deck a US Coast Guard–licensed captain trims the sails, and the city becomes a moving map: the domed silhouette of Adler Planetarium, the colonnades of Soldier Field, and the vertical rhythm of the Loop. Lake Michigan has its own personality here — a wide, cool current that nudges the bow and lifts the view.
Chicago’s lakefront grew from reclaimed shoreline and industrial piers into public space over the 20th century; Navy Pier opened in 1916 and long served military, commercial, and entertainment roles. Geologically, the lake sits on glacial scours carved at the end of the last ice age; that depth gives the water a steady, sometimes brisk motion and clear sightlines back to the city.
This private two-hour charter is flexible: ask to circle major landmarks, chase sunset light, or drift for skyline photos. The captain will offer historical anecdotes on request but this isn’t a walking tour — it’s a maritime experience built around your group.
Practical notes: expect light spray and cooler temperatures on-deck even on warm days, bring layered clothes, non-slip shoes, and sun protection. Boarding begins at the Navy Pier Marina; arrivals late may shorten your sail. The captain controls route and safety decisions; weather will dictate whether a sail proceeds or is rescheduled.