Begin your Kentucky adventure in Covington, where you’ll enjoy a blend of Northern Kentucky charm and vibrant city views across the Ohio River. After checking into your hotel, take a stroll through the quaint MainStrasse Village, a German-inspired neighbourhood with colourful buildings, unique boutiques, and the charming Goose Girl Fountain. For scenic views, walk across the Roebling Suspension Bridge and take in the Cincinnati skyline as the sun sets. Dinner options are plentiful, with local favourites like Bouquet Restaurant offering seasonal, farm-to-table cuisine, or Libby’s Southern Comfort for classic Southern dishes. Afterward, relax and prepare for the road trip ahead.

Enjoy breakfast before hitting the road toward Lexington. Take a leisurely drive through Kentucky’s picturesque bluegrass landscapes, arriving in Lexington where we recommend a horse farm tour. Explore iconic destinations like Claiborne Farm or Kentucky Horse Park to immerse yourself in Lexington’s renowned equine culture. In the evening, head downtown for a meal at Dudley’s on Short, known for its Kentucky-inspired menu and historic ambiance. If time allows, take a stroll around the Lexington Distillery District, where art galleries, shops, and craft breweries give a taste of local culture.

Start your day with a visit to a nearby bourbon distillery such as Woodford Reserve or Buffalo Trace for a tasting tour to sample some of Kentucky’s finest spirits. Back in Lexington, dive into the city’s charm with a walk around downtown, stopping by shops and cafes or the famous Crank & Boom Ice Cream Lounge for a treat. Later, visit Keeneland Racecourse to tour the stunning grounds or catch a live race if in season. End the day with dinner at one of Lexington’s classic eateries, such as Tony’s of Lexington for steak or Lockbox for a modern twist on Southern favourites.

Leave Lexington and head south toward Bardstown, arriving just in time to visit My Old Kentucky Home State Park, where you can take a tour of the historic mansion. Later, visit the Bourbon Heritage Centre or Barton 1792 Distillery to learn about Bardstown’s deep connection to bourbon. In the evening, we recommend you dine at The Rickhouse Restaurant, known for its local ingredients and extensive bourbon menu, before settling in for a restful night in this charming town.

Depart Bardstown for a scenic drive to Bowling Green, with plans to explore the National Corvette Museum upon arrival. This museum celebrates America’s sports car with interactive exhibits and classic Corvette models. Later, take an underground boat tour at Lost River Cave, a unique adventure through a historic cave system. End the day with dinner at 440 Main or Novo Dolce, where local flavours and Southern hospitality make for a satisfying meal.

Continue your journey with a drive to Louisville, Kentucky’s largest city. Your first stop should be Churchill Downs, home of the Kentucky Derby, where you can tour the Kentucky Derby Museum and experience the excitement of this iconic racetrack. Then, head to Louisville Slugger Museum & Factory to see how the famous baseball bats are made and even take home a mini-bat souvenir. For dinner, explore Whiskey Row and dine at Doc Crow’s or Repeal for an authentic taste of Southern cuisine paired with a bourbon cocktail.

Start your day in the trendy NuLu Neighbourhood, known for its eclectic shops, art galleries, and cafes. After exploring, stop by the Muhammad Ali Centre to honour Louisville’s legendary boxer and humanitarian. Stroll along the Ohio River waterfront in the afternoon to enjoy scenic views and photo ops, then head to Butchertown Grocery or Jack Fry’s for dinner, where you’ll find local favourites and upscale twists on Kentucky classics.

Depart Louisville for a short drive to Shelbyville, known as the “Saddlebred Capital of the World.” Spend the morning touring a local Saddlebred horse farm like Undulata Farm or head to Shelby Trails Park for a scenic horse ride through the countryside. Later, enjoy a tasting and tour at Jeptha Creed Distillery, where family-owned traditions meet innovative spirit-making. Relax in Shelbyville for the evening and consider dining at Bistro 535 or a charming local diner.

Make your way back to Covington, stopping along the way for a final day of exploration. Consider a short detour to Cincinnati across the river, where highlights include Findlay Market, Fountain Square, and the Cincinnati Art Museum. Wrap up your journey with a farewell dinner at Otto’s in Covington, where you can reminisce about your travels while enjoying locally inspired dishes in a cosy setting.

Spend your last day leisurely exploring Covington and nearby Cincinnati. Walk along the Ohio River for beautiful views, or visit the Cincinnati Art Museum, just across the river, to view an impressive collection of artworks. For lunch, stop by Findlay Market, Ohio’s oldest continuously operated public market, where you can sample local specialties. In the afternoon, return to Covington for any last-minute shopping or riverside views before concluding your Kentucky journey.