Bluegrass Country & the Smoky Mountains

Welcome to Louisville, Kentucky, famous for Thoroughbreds, world-class bourbon, and baseball heritage. Settle in for a 2-night stay at your downtown hotel. Today, there are no included activities, so the day is yours to enjoy at leisure. Perhaps you’ll take a stroll down Louisville’s historic Main Street, famously known as Whisky Row and Museum Row, lined with a variety of museums, bourbon distilleries, and tasting rooms.

Kick off your adventure at Churchill Downs, home of the legendary Kentucky Derby. Take an opportunity to meet with a retired jockey to learn about life on the track. Feel the thrill of the “Sport of Kings” as you delve into the racetrack’s storied past at the Kentucky Derby Museum. Continue to Bardstown, where history and heritage come alive at My Old Kentucky Home, an estate named for the song it inspired American composer Stephen Foster to write. Tour the stately mansion and walk the plantation grounds, gaining insight into both the family who lived there and the lives of the enslaved people who shaped its story. Later, immerse yourself in the art of bourbon-making with a behind-the-scenes tour at Jim Beam Distillery. Watch the distillation process in action and savor a tasting of this signature spirit. Tonight, join your fellow travelers at a local restaurant for a welcome dinner.

Before departing your hotel, start with a tour of the Seelbach’s haunted history, secret passageways and scenes from The Great Gatsby. Then, head to Museum Row, where it’s your choice! Step up to the plate at the Louisville Slugger Museum & Factory for an All-Star baseball experience -OR- explore the Frazier Kentucky History Museum and its “Spirit of Kentucky” exhibit, the official starting point of the Bourbon Trail™. Then, journey toward Lexington, pausing in the quaint, historic town of Midway. Approaching Lexington, the landscape transforms into a patchwork of rolling bluegrass hills and white-fenced horse farms. A local guide brings Kentucky’s equestrian heritage to life as you visit private farms and hear stories of the region’s most celebrated residents — its horses. Settle in for a two-night stay in Lexington.

Travel to Berea, the historic college town known as the Folk Arts and Crafts Capital of Kentucky. Meet some local artisans while they demonstrate their crafts. Then, explore Kentucky’s musical legacy at the Kentucky Music Hall of Fame. Explore exhibits filled with instruments, memorabilia, and stories that celebrate the state’s deep roots in bluegrass, country, and beyond. Tonight, take in the tastes of Kentucky at a local restaurant.

Travel through Daniel Boone National Forest, named for the legendary frontiersman who once carved paths through these wild Appalachian lands. Step into the soul of Appalachia at a living history village that brings the region’s culture to life. Begin with a hearty Southern-style lunch — served with a side of live bluegrass music. Then, take time to explore the museum’s cabins, barns, and artifacts and hear from a local about the resilient people who’ve called these mountains home for generations. By late afternoon, arrive in Gatlinburg, gateway to the Great Smoky Mountains National Park and your home for a two-night stay. The evening is yours to explore — perhaps stroll through downtown or take advantage of provided transportation to Dollywood,* Dolly Parton’s Smoky Mountains theme park (reservations and admission are on your own).

With a local guide, explore Great Smoky Mountains National Park (UNESCO), the United States’ most visited national park. During today’s drive, stop at various lookouts on the way to Newfound Gap, which boasts views of both Tennessee and North Carolina. Enjoy a picnic lunch in the park before continuing to the town of Cherokee. Enjoy some time to browse Native American art and souvenir shops or perhaps visit the Museum of the Cherokee. Later, return to Gatlinburg for a visit to the Ole Smoky Moonshine Distillery. Sample a variety of moonshine flavors — once an illicit Appalachian tradition, now a celebrated craft. Spend the evening as you wish.

Say goodbye to the Smokies and set your sights on Asheville, North Carolina, a city nestled in the heart of the Blue Ridge Mountains. The afternoon and evening are yours to explore a city known for craft breweries, chocolate, and farm-to-table cuisine. This evening, you may choose to join an optional tasting tour that introduces you to Asheville’s food scene, sampling local specialties and meeting the makers behind them.

Back in 1895, George Vanderbilt II decided to build himself a “little mountain escape” in the Blue Ridge Mountains of North Carolina. The result was the impressive and decadent grandeur of the Biltmore Estate. Step into a world of elegance as you tour the sprawling mansion and manicured grounds. Tonight, gather for a farewell dinner at a local restaurant and toast to an unforgettable journey.

Your tour concludes in Asheville. Proceed to Charlotte, about a 2-hour drive, for your flight home.