Distance from Milwaukee: 50 miles
Why Go: Years ago this lakeside enclave was a summer-home haven for Chicago’s elite, families like the Sears and the Wrigleys, whose mansions still grace Lake Geneva. The downtown boasts adorable shops selling luxury soaps, goods imported from Ireland, and gotta-have-it kitchen gadgets. There are also a few wineries with tasting rooms, such as Studio Winery (live music on Saturday afternoons).
Cruise around the lake on a guided tour from Lake Geneva Cruise Line. Accommodations range from historic bed-and-breakfasts like Maxwell House and Baker House to the comfy-and-luxe Grand Geneva Resort, with a spa, golf course, a steakhouse, firepits, a pool and plenty of on-site recreation.
Distance from Milwaukee: 154 miles
Why Go: The gateway to this peninsula county in Northeastern Wisconsin is Sturgeon Bay (www.sturgeonbay.net), a sailing mecca with a cute downtown. Head further north and you’ll pass through the pedestrian-friendly, petite towns of Egg Harbor, Fish Creek and Sister Bay. An ice-cream cone at the 110-year-old Wilson’s Restaurant & Ice Cream in Ephraim is a must, as is touring the Cana Island Lighthouse and booking a table for a fish boil (The Old Post Office in Ellison Bay; and Pelletier’s Restaurant & Fish Boil in Fish Creek both fold in theatrical performances that bring this culinary tradition to life).
Cocktails at Fred and Fuzzy’s Waterfront Bar & Grill channel a Key West vibe and taking the ferry to Washington Island reminds of bygone eras (tip: check out the lavender farm, Fragrant Isle. Home to five state parks, four of them feature camping, with Peninsula State Park in Fish Creek a popular choice with its lighthouse, beach and performing-arts theatre (Peninsula Players Theatre).
Distance from Milwaukee: 79 miles
Why Go: Home to the country’s largest farmers market (Saturdays from May through November from 6 a.m. to 1 p.m. on the Capital Square), Madison also offers a contemporary-art museum (Overture Center for the Arts) and eclectic dining and shopping (both the museum and these restaurants and shops are on the pedestrian-only State Street, which connects the State Capitol Building—open for tours—with the University of Wisconsin-Madison). On the far east side of town, along the isthmus (so named for being sandwiched by Lake Mendota and Lake Monona), is Olbrich Botanical Gardens, with an authentic Thai pavilion. A trip to Wisconsin’s capitol city would not be complete without enjoying ice cream crafted on the university’s grounds or a cold local beer at the university’s Memorial Union along Lake Mendota, with amazing lake views and, on some nights during the summer, live music. Both the Edgewater Hotel and Hotel RED are two of the city’s premier lodging options.
Distance from Milwaukee: 118 miles
Why Go: The arts scene here is anchored by the American Players Theatre, which hosts a mix of indoor and outdoor performances all summer long several nights a week, drawing upon scripts by Shakespeare and other playwrights alike with professional actors taking to the stage.
You’re encouraged to pack a picnic and eat on the grounds before curtain time. Another marvel in Spring Green is Frank Lloyd Wright’s former Wisconsin home, Taliesin, which he designed and built in 1911. It’s open for tours during the summer months. Spring Green has a well-liked independent bookstore with a small café (Arcadia Books) and the art galleries are run by some of the state’s best artisans, who make a living in pottery, painting, photography, furniture-making, printmaking and other mediums. House on the Rock Resort—so named for its nearby attraction of the same name—is a luxury option whereas the Usonian Inn is more economical (but was designed by a Wright protégé). Kayaking or canoeing down the Wisconsin River and pitching a tent at the Wisconsin Riverside Resort is another option.