4-Day Kentucky Bourbon Trail Tour from Louisville

DAY 01 | BOURBON BARONS

Louisville walking tour ⋅ Bourbon flight ⋅ Barbeque feast    

Our spirited journey begins in Louisville, the heart of Kentucky bourbon country and a cheerful riverside city with a mashup of neat neighborhoods ripe for exploration. Together with new friends and the local Tastemaker who will bring this extraordinary trip to life, we’ll hit the streets for a walking tour of historic Old Louisville, hearing the stories of bourbon barons, racetrack royalty, and tobacco titans. As our thirst for knowledge grows, we’ll make our way to a woman-owned watering hole for a bourbon flight and masterclass on Kentucky bourbon in warm and welcoming surroundings.

This evening, we’ll roll up our sleeves to chow down at a BBQ spot that features perfectly smoked meats paired with scratch-made sides and rounded out with a classic banana pudding so delicious it could be outlawed. Later, we’ll raise a glass to new friends and a music scene on Whiskey Row that is absolutely buzzing. 

DAY 02 | DISTILL IT DOWN   

NuLu food tour lunch  ⋅ Rabbit Hole tasting ⋅ Axe warfare happy hour 

After your kind of Kentucky breakfast, we’ll come together in NuLu, Louisville’s trendiest neighborhood, for a tasting tour of Kentucky classics like bourbon balls, fried chicken, hearty burgoo, and sorghum cookies. Along the way we’ll visit a historic home once occupied by Thomas Edison and take in the colorful streets painted with vibrant murals whose art galleries and eclectic shops are a feast for the senses. Brains and bellies brimming, we’ll join some master distiller friends for an immersive distillery tour and extended tasting at Rabbit Hole Distillery. Here, among these architecturally significant surroundings, we’ll learn how grain transforms to whiskey and how the founder’s jump ‘down the rabbit hole’ has changed the bourbon landscape forever. 

After time to refresh at the hotel, we’ll come together to raise a glass and an axe at an axe-throwing happy hour with a sharp learning curve. Dinner this evening will be the opportunity to choose your own adventure at one of Louisvilles’s delightful restaurants. Whether you want a full-blown Southern spread or the ‘hot brown’ sandwich that Louisvillians love, there is something delicious here for everyone. 

DAY 03 | HORSING AROUND 

Museums or market ⋅ Farm-fresh lunch ⋅ Horses of course 

This morning we’ll have the chance to follow our own Louisville passion. Besides the liquid arts there is much to see and do in this vibrant town - head to Logan Street Market for a look at what’s on offer, visit the derby’s Churchill Downs, or see where Cassius Clay lived before he became Muhammad Ali. Also highly recommended is the newly opened Roots 101 African American Museum, which explores issues of identity and social justice alongside displays of West African sculptures and the brass instruments of the blues.  

Early afternoon, we’ll hit the road for new pastures. Our destination will be historic Hermitage Farm for an exploration of the rural side of Kentucky life and the unique agricultural heritage and signature industries of the area. Our day on the farm will start with an organic farm-to-table lunch before we sample some bourbon, learn about thoroughbred culture from the horse’s mouth, and get high on the hog with a tour of the farm’s contemporary art collection. 

This evening after a final round of bourbon cocktails expertly blended by a mixologist friend, we’ll head to dinner at Proof on Main, a place beloved by local bourbon-makers due to a locally-sourced menu that expertly pairs with the hefty list of bourbons on offer. Together we’ll raise a glass to new friends, rich flavors, and the dedication to tradition that keeps the good times flowing. 

DAY 04 | UNTIL NEXT TIME

This morning after a leisurely breakfast it will be time to say goodbye for now.