Cruise Port Guide
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
Glide along the Chicago River on an expert-led architecture cruise past 50+ landmark skyscrapers. A bucket-list window into the city that invented modern architecture — seen best from the water.
Step onto The Ledge — a glass-floored balcony jutting 4.3 feet out of the 103rd floor of Willis Tower, 1,353 ft above Chicago. One of the most thrilling vantage points on earth.
Cover all of Chicago's iconic neighborhoods — Magnificent Mile, Millennium Park, Gold Coast, Navy Pier — on a premium open-top double-decker with live commentary. The perfect luxury orientation for a time-rich port day.
Chicago's legendary independent architecture boat tour, running since 1987, narrated by knowledgeable guides past 50+ landmark buildings on the Chicago River. An intimate alternative for those wanting a smaller vessel and a classic experience.
Soar 200 feet above Lake Michigan in a climate-controlled gondola on the Centennial Wheel at Chicago's iconic Navy Pier — one of America's most visited lakefront destinations, delivering skyline panoramas that stop the clock.
Chicago's premium multi-attraction pass bundles Skydeck, the Shedd Aquarium, the Field Museum, and more into one seamlessly curated luxury day. The savviest way to experience Chicago's world-class cultural institutions.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.