Three Days in Southern Indiana

THIS SOUTHERN INDIANA ITINERARY AT A GLANCE

Step into Southern Indiana’s fall charm, where historic river towns meet sweet traditions, steamboat history, and rolling wine country. Over three days, you’ll sample handcrafted candies, stroll fossil beds older than dinosaurs, and toast the season in Starlight’s vineyards all while soaking up the warmth of Hoosier hospitality.

Enjoy These Indiana Attractions and More:

Culbertson Mansion State Historic Site
Union Game Yard
Howard Steamboat Museum
Huber’s Orchard, Winery & Starlight Distillery
Downtown New Albany

Explore the February issue and subscribe for more group travel insights.

Day-to-Day Southern Indiana Itinerary

DAY 1: Historic Charm & Sweet Traditions in Indiana

Begin your escape in New Albany with a guided tour of the Culbertson Mansion State Historic Site. Built in 1867, this Victorian showpiece brims with ornate woodwork, elaborate frescoes, and stories of one of Indiana’s most prominent families. It has over 20 rooms and sits next to the Ohio River.

By midday, move your way up the river to Jeffersonville and step into Schimpff’s Confectionery. Experience a live candy-making demo to start your visit with the hypnotic swirl of molten sugar. Then, go for a stroll through the attached candy museum brimming with vintage delights and a generous dash of sweet nostalgia.

Another fun option is to visit a 600-acre farm, Huber’s Orchard, Winery & Starlight Distillery, where group tours showcase vineyards, distilling rooms, and tasting flights that span from sweet wines to small-batch bourbon. Stroll the farm market for seasonal produce, gourmet treats, and house-made jams. Starlight Distillery is Indiana’s mostaward-winning, farm-to-bottle distillery. It has won a variety of awards, including Best Overall Bourbon in 2025, Best in Class Best Special Barrel-Finished Bourbon (2025), and Best in Class Best Craft Distiller Whiskey (2025).

Lunch is a Southern Indiana classic at Joe Huber’s Family Farm & Restaurant with platters of crispy fried chicken, garden-fresh vegetables, and desserts that taste like grandma’s kitchen.

The day wraps in Clarksville at Derby Dinner Playhouse, where a hearty buffet and a Broadway-style musical make for an ideal all-in-one night of entertainment. A perfect finaleto a standout first day.

Explore the February issue and subscribe for more group travel insights.

DAY 2: Indiana Steamboats, Fossils & Local Flavor

Start your morning at Falls of the Ohio State Park in Clarksville to marvel at the world’s largest exposed Devonian fossil beds, a 390-million-year-old prehistoric timeline etched in stone.

Then head to the Howard Steamboat Museum in Jeffersonville, where a Victorian mansion houses intricate models, artifacts, and the legacy of America’s steamboat era.

Take a nostalgic, magical mystery tour over Memorial Day weekend at Abbey Road on the River, the world’s largest Beatles-inspired musical festival, which takes place May 21-25,2026 at Big Four Station Park in Jeffersonville.

For lunch, relax with riverside views at Upland Brewing Company, where seasonal craftbeers pair beautifully with hearty pub fare.

In the afternoon, explore rotating exhibits as well as the history of New Albany’s involvement with the Underground Railroad during the 1800s at The Floyd County Carnegie Library Cultural Arts Center in New Albany.

The evening’s grand finale is at MESA: A Live Dining Show. Watch as local chefs prepare each course before your eyes, weaving culinary stories between bites for a truly interactive dining experience.

DAY 3: Indiana Wine Country

Enjoy lunch at Union Pub & Social, an indoor-outdoor playground for all ages with yardgames and casual eats. It is the perfect setting for larger groups. Afterward, tap into your creative side at Pinot’s Palette, painting and sipping your way through an instructor-led art session that’s as much about laughter as it is about brushstrokes.

Spend the rest of the afternoon in downtown New Albany or Jeffersonville for last-minute shopping before you depart.