For group tour planners looking for a way to attract new and returning clients, an urban adventure might be your ticket. Urban adventures—explorations within cities—are enticing for travelers because they allow clients to cram a lot into their trip without breaking the bank or taking multiple road trips. As such, they might feel they are getting the most out of their travel experience for the cost.

Likewise, these trips allow planners to offer something that appeals to a broad clientele, because there is usually something for everyone on an urban adventure. If you’re considering planning such a trip, there are many options to choose from in all regions of the United States, but a good starting point is no place other than in the Heartland.

Chicago’s Many Attractions

There is no better destination to begin an urban adventure than in Chicago, Illinois, according to Lynn Osmond, president and CEO of Choose Chicago. “Chicago is a bucket list for all types of travelers,” she says, noting those who like outdoor settings will love the Windy City. “We have so many options for outdoor activities that many visitors may not be aware of.”

Chicago received its nickname in 1876 when a newspaper editor at the Cincinnati Enquirer dubbed it the “Windy City,” referring to the area’s frequent windstorms—and perhaps as a slight to local politicians he deemed to be “full of wind.” The name stuck, and the city and state have even promoted it in their marketing. Much like the breezes that blow through the area, the city is home to other constants, including a vibrancy that has only deepened over the decades.

“Tour groups in Chicago can explore Lake Michigan by boat or kayak (or even scuba diving), or they can visit any of our downtown or neighborhood-based boat and kayak rentals along the Chicago River that offer more peaceful experiences on the water and opportunities to get a bit closer to the wildlife that thrives in our urban environment,” she says. “Our beaches are also an incredible asset to both residents and visitors; many Chicagoans love nothing more than spending the day at the beach in the summertime.” Hop on a bicycle to explore the city’s 22-mile lakefront trail.

“For those not into biking or watersports, we also have a beautiful public parks system throughout Chicago, some that include superbly manicured gardens and lawns, some with fabulous old infrastructure dating back to the early 20th century, and some with expansive wooded areas that can make you forget you’re in the middle of a massive city,” Osmond says. “The Chicago Riverwalk offers a beautiful vantage point for viewing our world-famous downtown architecture with 1 1/4 miles of walkway on both sides of the river, making for a nice 2 1/2-mile round trip.”

Groups visiting in winter can experience ice skating at the rink called the Maggie Daley Park Ice Skating Ribbon or at the iconic Millennium Park ice rink. There’s also snowshoeing and cross-country skiing at city parks or the Cook County Nature Preserve. Take a deep dive into the arts and culture of the area with its museums, or walk through stunning indoor gardens at the Lincoln Park and Garfield Park conservatories. Osmond says, “Visitors would be well-advised to “just explore” and be open to new experiences.”

Eiteljorg Museum, Indianapolis, Indiana;
Credit: Visit Indy
Adventure in Indianapolis

The sky over Indianapolis, Indiana, will dim for a period during the total eclipse on April 8. Makes sense since the city lies in the “path of totality”—locations where the moon’s shadow completely covers the sun—and Indy is planning many activities in and around the city for the solar event.

But you don’t have to visit Indy this April only to experience adventure. No matter the time of year, there are any number of activities and places to experience for tour groups that might seem just as heavenly.

Try White River State Park—dubbed “Indy’s backyard”—which promises a hub of offerings in what Visit Indy describes as “your perfect urban getaway.” Comprising 250 acres, the park welcomes 3 million annual visitors who come here to visit the seven main attractions of the complex: The Children’s Museum of Indianapolis, Conner Prairie outdoor museum, Eiteljorg Museum, Indiana Historical Society, Indiana State Museum and Historic Sites, Indianapolis Zoo, and Newfields—a 152-acre campus that features renowned art galleries, gardens, and a historic home. Don’t worry about feeling claustrophobic, because there also are miles of trails and greenspace to explore.

Visitors also can share in America’s favorite pastime by catching a baseball game at Victory Field. If sports are not on the list, how about attending a concert at the Everwise Amphitheater at White River State Park? Or, find the area’s many iconic memorials. Did you know Indy is second to Washington, D.C., when it comes to the number of monuments? Explore farther along the Indianapolis Cultural Trail that comprises 8 miles of trails that connect all six of Indy’s Cultural Districts.

Make Memories in Milwaukee
Harley-Davidson Museum, Milwaukee, Wisconsin;
Credit: Visit Milwaukee

Another great adventure is Milwaukee, Wisconsin. “Milwaukee is a major urban destination that’s manageable for groups of all sizes,” says Megan Husband, national account and tourism sales executive with Visit Milwaukee. “Due to its Midwest location, Milwaukee has always been a great place for day and overnight trips and because it offers dozens of attractions in an easily accessible and navigable footprint. From cultural attractions and festivals to professional sports and one-of-a-kind museums, groups can easily experience a huge variety of attractions and activities in our city and region.”

Some of the ways to experience the area is with the Discover Iconic Milwaukee city tour, enjoyed aboard one of its ecofriendly cruisers or buses. Participants can expect to see Milwaukee’s highlights—the famous spots that put Milwaukee on the map as well as a few hidden treasures that many locals don’t even know about. The tour makes a giant sweep through the city, covering its famous brewery and bar districts but also its museums and hotels; lakefront and historical architecture; walking and biking trails; and sculptures by local, national, and international artists featured through Sculpture Milwaukee.

“Starting your time in Milwaukee on a guided tour is a great way to take in all of Milwaukee’s diverse neighborhoods and understand our city’s history,” Husband says. “Our architecture and culinary scenes are world-class, and our location on the shores of Lake Michigan offers a completely unique feel from many other midwestern destinations.”

There is also the Historic Third Ward and the Harley-Davidson Museum. At the Harley-Davidson Museum, guests will find culture and history through stories and interactive exhibits that celebrate expression, camaraderie, and love for the sport of riding a Hog. Along with its collection of Harley-Davidson motorcycles and memorabilia, the site has exhibits, shopping, dining, and a full calendar of activities.

“People from across the globe travel to Milwaukee to experience this American icon,” Husband says. “Seeing the world’s one and only Harley-Davidson Museum is a bucket list item for many travelers. Whether it be fashion, military history, or pop culture, the museum truly offers something for the enthusiast—the newly curious or casual museum goer.”

What’s a visit to Milwaukee without trying its tasty eats? Milwaukee Food and City Tours, which encourages groups to uncover the hidden gems of the vibrant west side of Walker’s Point neighborhood, is renowned for its craft breweries and flavorsome delights. Here, visitors will stroll through the historic district and can visit notable establishments where they can sample myriad tasty treats.

Paisley Park, Chanhassen, Minnesota;
Credit: Explore Minnesota
Minnesota’s Twin Cities

Another place to find urban adventures for tour groups is Minnesota’s Twin Cities. Minneapolis and St. Paul are meccas for art and culture, and tour planners won’t be disappointed booking a trip here.

A must-stop is the famous Mall of America in Bloomington, the largest indoor mall in the country. With its more than 500 retail stores, 50-plus restaurants, an indoor theme park, Minnesota’s largest aquarium, and a mini-golf course, there is surely something for everyone.

Take in a play at the Guthrie Theater, located on the Mississippi riverfront, where plays both classic and contemporary are performed. Backstage tours are offered on Fridays and Saturdays. On the Mississippi, take a cruise with Padelford Riverboats, which offers both public and private tours from Memorial Day through Labor Day. History lovers will enjoy a visit to the James J. Hill House, a 36,000-square-foot mansion in St. Paul completed in 1891 for railroad magnate James J. Hill. “ere’s also an art gallery on-site, free to the public.

Several celebrities have roots in Minnesota as well, but one of the most iconic is the musician Prince, who not only left a musical legacy—including a vault of hundreds of recorded but unreleased songs—but also a remarkable studio that served as his production venue, concert hall, and home. He named it Paisley Park, the same as a music label he created in the 1980s and song by the same name.

Today, eight years after the rock star’s passing, Paisley Park is open for guided tours, where guests can see where Prince lived and worked. Besides the guided tours, the site has a gift shop open most days. While here, stop in the lounge area to hear Prince music, watch music videos, see a stage display, and “go crazy” with cookies or cheesecake the rock star enjoyed. The cherry-flavored hot chocolate is also a tasty treat.

By Andrew Weeks

Main Image: Urban kayaking in Chicago, Illinois; Credit: Choose Chicago/Graham Chapman