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 aboard a private charter as a world-class architect narrates the stories behind the city's iconic skyline. This is the definitive way to witness the greatest concentration of architectural genius on the planet.
Step out on the glass-floored Ledge of the Willis Tower — 1,353 feet above the city — then cap the evening on Navy Pier watching the famous fireworks over Lake Michigan. Chicago's two most breathtaking vantage points in one unforgettable day.
Dive fork-first into Chicago's legendary food culture — from the birthplace of deep-dish pizza in River North to Chicago-style hot dogs, Italian beef, and craft cocktails in the West Loop. A private local guide takes you behind the scenes of the city's most iconic culinary institutions.
Trace the roots of American music on an expert-led private journey through the South Side's legendary jazz and blues corridors, culminating in an exclusive session at an intimate live-music venue. This is where Muddy Waters electrified the world.
Experience one of the world's top five art museums — home to Seurat's 'A Sunday on La Grande Jatte' and Grant Wood's 'American Gothic' — with a private art historian who unlocks the stories behind the masterpieces. Bucket-list culture, at its purest.
Paddle silently through the heart of Chicago at dawn on a private kayak tour of the city's hidden river channels — the most intimate, extraordinary perspective of the skyline you will ever experience. The city wakes up around you.
⚓ 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.