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10 Days 9 Nights
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1 Independent - Self Drive
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Venture Insight

Founded when early American settlers first began their expansion west, the states of Tennessee and Kentucky were born of boundary-pushing and self-determination. Today, you see those same characteristics in the culture, the cuisine, the music, and the spirits — bourbon spirits — that make this region in the American South unique in all the world. In one short trip, you’ll journey through where the bluegrass grows and bourbon flows, meet makers and musicians, and take part in a history and heritage that still runs deep. Welcome to the Bluegrass and Bourbon Trail.

Blues + Barbecue in Memphis

Your adventure kicks off where legends are born — Memphis, Tennessee. The birthplace of rock‘n’roll and home to “The King of Rock‘n’Roll” himself, Elvis Presley.  Memphis has a long and rich musical heritage and today you can still hear the sounds of soul, R&B, jazz, blues, and rock‘n’roll flowing through the street every night of the week.

Of course, that street is the world-famous Beale Street!  Memphis’ musical epicentre. Head to B.B. King’s Blues Club for a Memphis trio: blues, barbecue, and bourbon.

Next, it’s off to see “The King’s” castle at Graceland Mansion. Here, you’ll take a fascinating tour through the personal and professional life of one of the world’s most influential music icons. Then you’ll continue your journey through music history at the famous Sun Studio where artists like Elvis, B.B. King, Jerry Lee Lewis, and Johnny Cash got their recording starts

Tennessee Whiskey Awaits in Lynchburg

From Memphis, head west to Lynchburg, a tiny Tennessee town with a huge legacy: it’s home to Jack Daniel’s Whiskey. Take a fascinating tour through the Jack Daniel’s distillery and learn about the careful crafting that goes into creating one of the world’s most recognisable whiskey brands, including a look inside the whiskey’s pure and only water source — Cave Spring Hollow, a natural cave spring.

After your distillery tour, visit Barrel House 1-14, one of the first barrel warehouses built by Jack Daniel at the end of Prohibition in 1938, for a one-of-a-kind whiskey tasting. Then, it’s off for another tasting, this time at Nina’s Taste of Tennessee, where you’ll indulge in hand-crafted boozy sweet treats and chocolates.

City + Mountain Scenery in Chattanooga

Hit the road to Chattanooga. Located in the foothills of the Appalachian Mountains and on the banks of the Tennessee River, Chattanooga is home to stunning scenery and endless opportunities for outdoor recreation. Combine that with the recent revitalisation of Chattanooga’s downtown and riverfront, and the city has aptly earned its title as the “Best Town Ever.”

For a bit of Tennessee history, it’s off to Chattanooga Choo Choo Hotel. Originally built in 1908 as a terminal for the Southern Railway, the converted Chattanooga Choo Choo building is now a historic hotel complete with restored sleeper cars.

To get a higher view, you’ll leave the city and journey up to the top of Lookout Mountain to take in spectacular panoramic views of the mountains and city from above a 100-foot cascading waterfall. Feeling thirsty? Head back down to Robar Cocktail Bar near the riverfront for a local bourbon whiskey.

Mountains + Moonshine in Gatlinburg

Cruise west until you reach the entrance of the Great Smoky Mountains National Park,. The gateway to one of America’s most popular national parks is the city of Gatlinburg, a mountain resort town known for its Appalachian hospitality and bustling booze scene. From authentic Tennessee moonshine to craft breweries, Gatlinburg is home to some of the state’s most creative distilleries.

Head to Ole Smoky Tennessee Moonshine, the first federally-licensed moonshine distillery in the state, for a fascinating tour through the history of moonshine, a look at the distilling process, and a taste of the award-winning ‘shine. Then, walk off your buzz with a stroll down Parkway, downtown Gatlinburg’s main thoroughfare, where you’ll peruse the windows of quaint shops and busy restaurants.

Champions are Born in Lexington

Cross the state line and head to Kentucky’s Bluegrass Region where you’ll find the city of Lexington, also known as the “Horse Capital of the World.” But the city is not known for just any horses. Lexington produces some of the most stunning champion thoroughbred horses in the world — horses like the infamous Seabiscuit whose legendary life has been the subject of multiple novels and films.

From barn to bourbon, Lexington is one of the main stops on the “Kentucky Bourbon Trail” with four historic and six new craft distilleries. Take a tour through the distilleries to learn the fascinating history of Kentucky bourbon and to taste the smooth spirits.

Then head to the Kentucky Horse Park to see where champion horses are born before popping into the Visitors Bureau to pick up a Lexington Walk brochure that’ll guide you on a tour through historic downtown.

Off to the Races in Louisville

It is off to the races in Louisville, home of the world-famous Kentucky Derby horse race. But the Derby isn’t the city’s only claim to fame. Also known as “Bourbon City,” Louisville is the starting point of the Kentucky Bourbon Trail — which officially begins in the Frazier Kentucky History Museum — and is the only city in the country to offer an Urban Bourbon Experience.

Head downtown to the Frazier Kentucky History Museum for a taste of the state’s rich history that unfolds hand-in-hand with the history of Bourbon itself. Then, it’s off to Churchill Downs for a fascinating tour through the Kentucky Derby Museum and race grounds.

Lift your spirits on the Urban Bourbon Trail and sip America’s only native spirit in some of the best whiskey bars in the world. Old Fashioned cocktail, anyone?

A Musical Pilgrimage in Nashville

Nashville is next – known as “Music City,” it is home to such institutions as the Grand Ole Opry – which literally put country music on the map. Today, singers and songwriters, legends and up-and-comers, still flock to Nashville as a place of music pilgrimage.

For a bit of bluegrass history, visit historic Ryman Auditorium whose stage has hosted the likes of music royalty for ages, including “The Father of Bluegrass” himself, Bill Monroe whose bronze statue is on display outside the auditorium. Next up, it’s down to the Country Music Hall of Fame for an immersive tour through the history of country music.

You’ll Sing the Blues

Your trip ends where it began back in Memphis and there’s still time to lift your spirits. How about a Mint Julep?


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