Kentucky & Tennessee: The Complete Deep South Experience


All Year Round


From $9,310pp excl. flights
(based on 2 ppl sharing)

How long

9 nights ideal length

It’s time to unveil our take on an area of the USA full of hidden wonder and no-holds-barred-fun, the Deep South. To really get under the skin of Kentucky and Tennessee we’ve met with Bulleit Bourbon and George Dickel Tennessee Whisky to inspire us to create a Black Tomato trip that defines the spirit of their surroundings. Whether you’re looking for the finest whiskey, world class music, the thrill of the races or stunning rural beauty, this adventure has it all. But more than anything, few places on earth know how to have a good time quite like the Bluegrass and Volunteer states.

Kentucky Culture

Wake up slowly at the divine Brown Hotel in Louisville and be sure to have a hearty southern breakfast as we’ve organized a big day for you. After either a round of golf at the exquisite Vallhalla Golf Course or exploring the shops in the trendy NuLu district, take lunch at the acclaimed Proof on Main and sample the delicious artisan fare. From here Black Tomato will chauffeur you in a beautiful, vintage American convertible to The Bulleit Frontier Whiskey Experience at the Stitzel-Weller Distillery. Feel the wind in your hair and soak up the scenery.

Bulleit will roll out the red carpet with a grand tour on arrival. You’ll join a whiskey expert and learn the processes around producing the perfect tipple. After a few hours of tastings and invaluable insights, you’ll move on for an evening that brings an authentic Kentucky BBQ like no other, where a local pit master will personally teach you smoking and grilling techniques before you dine on the delicious produce.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

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Elegant Events & Old Traditions

Day Two means further immersion into Kentucky’s heritage for a day at the horseracing in Lexington. Nowhere in the world does it better. First, go behind the scenes at the elite Three Chimneys Racing stables for a tour of the stallion division before heading to Keeneland Racetrack for a fine day out with the best vantage point in the stands. You may even feel like a flutter. Spend the night at the chic 21C Museum Hotel in Lexington.

On your last morning in Kentucky, Black Tomato will take you into the great outdoors for some skeet (‘clay pigeon’) shooting. Breathe in the fresh air and take aim. Your trip to Tennessee is about to get a little bit rock n’ roll, or should we say ‘country’? You’ll be picked up to take the four hour trip to Nashville in a luxury tour bus used by the likes of Willie Nelson. We highly recommend asking your driver to stop off at Mammoth Caves on the way before cruising into town like a famous music star.

Nashville Nights

Wake up at the sophisticated Hutton Hotel, grab a coffee and head downtown. The Gulch district is home to buzzing shops and iconic conversion architecture. After a leisurely wander where you can enjoy both the shopping and the atmosphere, settle down for an authentic lunch at Martin’s BBQ. For the afternoon we’ll arrange a private tour of the Country Music Hall of Fame Museum and the famous RCA Studio B before having you write and record your own country song with a prestigious writer. Now that you’re feeling inspired, it’s time to experience as much incredible, live music as you can. Ryman Auditorium, Tootsie’s Orchid Lounge, Wildhorse Saloon and The Bluebird Café all provide exceptional talent, with differing scales of intimacy.

Tennessee Tastings

Back on board your tour bus (move over Willie) it’s time to make your way to George Dickel country near Tullahoma for another exquisite whiskey experience. Start with a two hour private tour of the distillery with a Dickel Whisky expert. Taste the liquid at each stage of the process from the mash tubs and fermentation to the distillation. This is the ultimate inside scoop on how the George Dickel signature chill charcoal mellowing process creates that smooth, legendary flavor.

You’ll then have the chance to sample, if you choose, liquid straight from the barrel, and get your hands on a limited release of one of the oldest Tennessee Whiskies around (c. 17 years old, in fact).  Then it’s time to head to the Post Office speakeasy for a classic Tennessee fried chicken lunch. Afterwards, indulge in games on the lawn, sample the George Dickel range, as well as your own, and relax in the sunshine as evening approaches. The final extravagance of the day is a short helicopter ride east to land at your final dwelling, the pure, rural bliss of Blackberry Farm, in the heart of the Smoky Mountains.

A Final Retreat

Waking at Blackberry Farm is as close to perfection as it gets. From your estate room, cottage suite or even entire house, the range of outdoor activities is endless, from hiking and fly-fishing to canoeing. If it’s more of a restful time you long for, don’t fret, the estate’s resident baker, cheese maker or chocolatier are all on hand to make sure you feel utterly spoilt. As night falls, sample the delicious wines at a private tasting, savor the organic cuisine or roll your sleeves up and embark on the chef’s sublime cooking course. The ultimate, wholesome end to a Deep South adventure.

Please Drink Responsibly.

Black Tomato is a UK and US based award-winning, luxury, bespoke travel company that delivers imaginative and cutting-edge travel experiences around the world. Black Tomato is not licensed to sell or distribute alcohol – any and all whiskies must be purchased at a licensed retail location.

Where to rest your head

The Hutton Hotel, Nashville

Welcome to the Music City, home to honky-tonks and underground bluegrass shows to satisfy the cravings of any culture vulture. The stylish Hutton Hotel is…
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Blackberry Farm, Tennessee

There are some secrets that are just too good to keep to yourself, and Blackberry Farm is definitely one of ours. Hidden in the misty…
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