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.
Soar above the Windy City in a private helicopter, tracing the glittering shoreline of Lake Michigan and the architectural giants of the Loop. A once-in-a-lifetime aerial perspective no street-level tour can rival.
Glide along the Chicago River aboard a private charter while a certified architect-guide unpacks the greatest concentration of landmark buildings on Earth. The definitive Chicago experience, done properly.
Explore the crown jewel of Chicago's lakefront with a private art-and-architecture guide who transforms a famous park into a living gallery. Cloud Gate, the Crown Fountain, Lurie Garden — experienced with expert context, not a selfie stampede.
Devour the real Chicago food story — legendary deep-dish pizza, Chicago-style hot dogs, and local craft beer — led by a born-and-bred Chicagoan on a curated neighborhood crawl. No tourist traps, just the real thing.
Step onto The Ledge — the glass-floored balcony jutting 4.3 feet beyond the 103rd floor of the Willis Tower — and gaze straight down 1,353 feet to the streets of Chicago. A vertigo-inducing bucket-list moment above the Midwest.
Uncover the darker, electrifying chapters of Chicago history — Prohibition speakeasies, Al Capone's empire, and the St. Valentine's Day Massacre — with a private expert historian on a cinematic walking and driving tour.
⚓ 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.