Start the morning with a pontoon boat ride on Carlyle Lake. Then explore nearby Eldon Hazlet State Park, featuring hiking trails and extensive nature programs. Next, roam the 90 acres of the lovely Cedarhurst Center for the Arts in Mt. Vernon. Here you'll find the sprawling Cedarhurst Sculpture Park and Mitchell Museum, showcasing contemporary artworks. Don't miss the Cedarhurst Craft Fair, held annually in September. Afterwards, sample the award-winning wines at GenKota Winery in Mt. Vernon. For lunch, try the down-home barbecue dishes at Triple E BBQ in Mt. Vernon. Then shop at the Southern Illinois Art & Artisans Center at Rend Lake in Whittington, featuring fine artwork and traditional crafts made by Illinois artists. Take time to peruse the rotating exhibits at the on-site Southern Illinois Art Gallery. Afterwards, head for Pheasant Hollow Winery, situated on the eastern shore of Rend Lake in Whittington. Enjoy a glass of fruit wine on the deck overlooking five acres of rustic woodlands. Pheasant Hollow regularly hosts a murder mystery dinner theater and live musical entertainment. In the evening, enjoy dinner with a sweeping lakeside view at Windows Restaurant, located at Rend Lake Resort in Whittington.

In the morning, lace up your hiking boots and make tracks to Giant City State Park, named for its sheer sandstone walls that create the appearance of soaring city streets. Enjoy a family-style fried chicken luncheon at Giant City Lodge. Afterwards, browse the artists' shops and galleries that populate the charming Makanda Boardwalk, near Giant City State Park. Located in the tiny town of Makanda, the shopping district features an actual boardwalk for strolling and browsing. In the afternoon, taste some of Illinois’ best vintages at stops along the Shawnee Hills Wine Trail near Carbondale. The trail is made up of 13 award-winning wineries located along a 25-mile scenic drive through the Shawnee National Forest. Be sure to check out Alto Vineyards, the largest (at 10 acres) and oldest winery in southern Illinois, and the beautiful Tuscan-themed Blue Sky Vineyard. Enjoy a gourmet dinner at Legends, a fine dining restaurant located at Walker’s Bluff, a scenic 160-acre complex in Carterville that includes a vineyard, general store and live entertainment. Catch a concert or theatrical performance in the evening at Southern Illinois University's Shryock Auditorium.

Drive along the Ohio River Scenic Route and take in the lush beauty of the Shawnee National Forest. Head for Fort Massac State Park & Museum in Metropolis, which features a replica of the original 1700s fort as it appeared during the French and Indian War. The museum displays items used under the French rule, as well as Native American artifacts. Then stop for a photo op with the 15-foot-tall Superman statue or the nearby Lois Lane statue in downtown Metropolis, the official adopted "Home of Superman." Across the street is the Super Museum, featuring amazing Superman memorabilia, movie props and a gift shop stocked with super souvenirs. The popular Superman Celebration, held every June in Metropolis, features superhero-themed entertainment and celebrity appearances. Have lunch at Cave-in-Rock Restaurant, located within Cave-in-Rock State Park (named for its waterfront cave). The restaurant is known for its homey Southern-style dishes, including fried catfish. Afterwards, discover unusual rock formations (including Camel Rock and the Devil's Smokestack) at the Garden of the Gods within the Shawnee National Forest, near Harrisburg. Be sure to hike the Observation Trail that leads to a stunning cliff-top panorama.