These 5 guided day trips on and off the water will give you a true taste of Chicago

Although Chicago offers plenty of architectural walking tours, the best view is unquestionably by boat. Sit back on an open-air deck as you traverse the Chicago River and learn all about the 130-year-long history behind the skyline’s most interesting skyscrapers. From the ornate, historic Wrigley Building and Tribune Tower to the imposing art deco Merchandise Mart and the circular Marina City Towers, you won’t believe how many sights there are to see while comfortably seated!

Hit up a museum and Chicago’s past seems to begin and end with the Great Chicago Fire, but if you’re interested in a “different” (and eerier) side, this family-friendly, expert-led tour will give you all the dark details. For starters, you’ll learn how Al Capone ran his mob empire and see the notorious places he’d carry out his, ahem, business. You’ll even get to sit back and soak in the vibe of a once-famous former gangster hangout. If Death Alley isn’t enough, you’ll even stop by some haunted locations before a visit to Congress Hotel, one of the most ghost-heavy spots in Illinois.

There are boats, and then there’s the Tall Ship Windy. The iconic 148-foot, 4-mast schooner is an experience in itself—nevermind the breathtaking sights you get to take in once aboard the traditional vessel. Glide over the shimmering waters of Lake Michigan and even try your hand at sailing: The crew happily teaches guests how to make maritime knots, hoist sails and even shoot the canon. The resident tour guide’s tidbits of local history and fun facts—from physics to ecology—turns the tall ship into a floating classroom fit—and fun—for the whole family.

Chicago is one of the nation’s best food cities, so why not take in the sights with a local snack? On this three-hour guided walk, you’ll get a literal taste of Chicago—and the foods it’s known for inventing and perfecting. Sample deep-dish pizza, enjoy a classic Italian Beef sandwich, savor the results of the original recipe brownie, and, of course, devour a Chicago hot dog. (For a slight upcharge, you can soak it all up with a few craft beer samples.) Bonus: this tour comes with a free two-hour bike or kayak rental!

If you weren’t lucky enough to snag tickets to a show at The Chicago Theatre, here’s one better: Go behind the scenes of the city’s most-photographed venue and admire the grandiose architecture and painted murals up close. You’ll even get to see what famous performers—including Frank Sinatra and Dolly Parton—see! Be sure to ask your tour guide about the “Chicago municipal device” and see if you can spot it in the landmark, six-story marquee.