Chicago · SAILING
This is the shortlist you would send a friend: 2 sailing trips worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Book a private two-hour sail for up to six people from Navy Pier Marina. Your Coast Guard-licensed captain, possibly Mike, Ulysses, or Rich, adjusts the route to the wind and your interests, with skyline views, Bluetooth music, and time for drinks on deck.
“Lovely morning sail on Lake Michigan with the skillful, personable and knowledgeable Captain Ulysses!”
Spend 90 minutes on a historic wooden yacht with a captain and architecture guide, cruising past the Wrigley Building, Riverwalk, Magnificent Mile, and Michigan Avenue Bridge. Expect nonstop commentary, soda, coffee, snacks, and a smaller boat experience, but plan for strong sun and limited shade.
“The guide lady was super knowledgeable and funny, we loved how everything was organized and that it wasn’t super crowded.”
Pick a river, a sidewalk or a plate.
