La Grange, IL Outdoor Activities

What looks like a crimson-hulled pirate ship glides into view from behind Shedd Aquarium. The wind picks up, surging into the schooner's 77-foot gaff-rigged topsails and speeding the vessel along Lake Shore Drive at 10 knots. Those on shore can just make out the boat's name, Red Witch, and what appear to be passengers raising a drink to the Chicago skyline.

Docked in Burnham Harbor, the Red Witch tall ship is one three vessels in Tall Ship Adventures of Chicago's fleet. Designed by naval architect John G. Alden and named after the book Wake of the Red Witch—the same story that inspired the film starring John Wayne and Gail Russell—the Coast Guard–licensed ship accommodates up to 49 passengers within its mahogany-over-oak frame. Having sailed waters off Maui and San Diego, the boat is now under the stewardship of Captain Andrew Sadock and his crew, which leads tour cruises, coordinates charter adventures, and autographs cannonballs for each passenger.

In addition to being a current member of the American Sail Training Association, the Red Witch finished among the finalists for Best Boat/Cruise Service Provider in the 2010 Illinois Meetings + Events Readers' Choice Best of Awards.

With a fleet of futuristic segways and classic beach-cruiser bicycles, Bike and Roll Chicago outfits travelers with wheeled transportation to explore the city’s paved surfaces. Tour guides lead groups through Millennium Park and along the lakefront to catch the skyline when illuminated by sunrises or backlit by one of Chicago’s many moons. Misty Lake Michigan breezes ruffle riders’ hair peeking through helmets as they pass by sailboats swaying lazily in the harbors and fishermen casting lines for trout and perch. Bike and Roll Chicago designs routes around classic architectural landmarks such as the Shedd Aquarium and Field Museum as well as popular neighborhoods home to a number of restaurants and art festivals.

Gliding through parks and weaving between runners on the lakefront path, segway-riding guides from Signature Segway Adventures keep guests in the know, offering up fun facts about the city and its origins. During tours, they highlight architectural sights, scenic views, and landmarks such as Buckingham Fountain, Navy Pier, and the Shedd Aquarium. Before hopping aboard a self-balancing vehicle, guests take part in an instructional course so they will feel confident and not try to bring their own training wheels from home.

A 30-foot sailboat floats across Lake Michigan. It churns through water twinkling with reflections of moonlight, stars, and the Chicago skyline. Suddenly, fireworks shoot into the air, painting the sky above Navy Pier in blooms of red and blue. The USCG–licensed and certified captains at 3rd Coast Cruising create moments like these during private charters and sightseeing tours. They also spend their days leading hands-on lessons that let sailors discover keelboarding or tackle more advanced conditions such as heavy-weather sailing. Launching from the giant wine bottles in DuSable Harbor, 3rd Coast Cruising's fleet also beckons potential captains to compete in sailboat races.