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7-Day Kentucky Road Trip Adventure Itinerary
Last updated: 2024 Jun 14Exploring Lexington's Heritage and Cuisine
Morning
Start your day with a visit to Ashland: The Henry Clay Estate. This historic estate offers a glimpse into the life of one of America's great statesmen, Henry Clay. The guided tour provides an in-depth look at the beautiful mansion and its well-preserved artifacts.
Afternoon
After exploring the estate, head to Coles 735 Main for a delightful lunch. This highly-rated restaurant offers a unique blend of Southern and contemporary cuisine. Post-lunch, embark on the Lexington Bluegrass Cocktails and Bites Walking Tour. This tour will take you through some of Lexington's best cocktail bars and eateries, offering a taste of local flavors.
Evening
For dinner, make your way to Tony's of Lexington, known for its exquisite steaks and elegant ambiance. End your evening with a leisurely stroll around downtown Lexington or visit one of the local bars for a nightcap.
Bedtime
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Ashland: The Henry Clay Estate
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Ashland: The Henry Clay Estate
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Lexington Bluegrass Cocktails and Bites Walking Tour
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Lexington Bluegrass Cocktails and Bites Walking Tour
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Horse Farms and Historic Tours in Lexington
Morning
Begin your second day with the From Lexington Kentucky Horse Farms Tour. This guided tour will take you through some of the most famous horse farms in the region, giving you an insight into Kentucky's rich equestrian heritage.
Afternoon
Enjoy lunch at Dudley's On Short, a charming restaurant known for its creative dishes and historic setting. Afterward, visit the Lexington The Aviation Museum of Kentucky Entry Ticket to explore fascinating exhibits on aviation history.
Evening
Dine at Jeff Ruby's Steakhouse, where you can indulge in premium steaks and seafood. If you're up for more exploration, consider joining the Lexington Downtown Walking Food & History Tour to learn more about Lexington's history while sampling delicious bites.
Bedtime
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4.94From Lexington Kentucky Horse Farms Tour
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4.94From Lexington Kentucky Horse Farms Tour
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4.90Lexington The Aviation Museum of Kentucky Entry Ticket
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4.90Lexington The Aviation Museum of Kentucky Entry Ticket
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Discovering Louisville's Rich Culture
Morning
Drive to Louisville in the morning (approx. 1 hour 20 minutes). Start your day with a visit to the Frazier History Museum, which offers engaging exhibits on Kentucky's history and culture.
Afternoon
For lunch, head to Jack Fry's, an iconic Louisville restaurant known for its Southern cuisine. Afterward, explore more of Louisville by taking part in the Louisville NuLu District Food and History Tour, which showcases the city's vibrant food scene and historic sites.
Evening
Dine at Proof on Main, located within the 21c Museum Hotel. This restaurant combines art with culinary excellence. End your evening with a visit to one of Louisville’s many bourbon bars or take part in a ghost tour such as the Louisville Old Louisville Walking Ghost Tour.
Bedtime
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4.80Frazier History Museum
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4.80Frazier History Museum
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4.75Louisville NuLu District Food and History Tour
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4.75Louisville NuLu District Food and History Tour
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Caves and Natural Wonders at Mammoth Cave
Morning
Drive from Louisville to Mammoth Cave (approx. 1 hour 30 minutes). Start your day early with a guided tour through Mammoth Cave National Park. The cave system is one of the longest in the world and offers various tours that showcase its stunning formations.
Afternoon
For lunch, dine at The Lookout Restaurant at Green River Grill, which provides hearty meals perfect after an adventurous morning. Spend your afternoon hiking some of Mammoth Cave’s scenic trails or visiting other natural attractions within the park.
Evening
Have dinner at Travertine Restaurant before heading back to your boutique B&B for some relaxation after an exciting day exploring natural wonders.
Bedtime
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Historic Trails and Scenic Views at Cumberland Gap
Morning
Start your day with a visit to the Cumberland Gap National Historical Park. This park offers a rich history of early American pioneers and stunning natural beauty. Hike up to the Pinnacle Overlook for breathtaking views of the surrounding landscape.
Afternoon
For lunch, head to The Portal Pizzeria, known for its delicious pizzas and cozy atmosphere. Afterward, explore more of the park by visiting the Hensley Settlement, a restored early 20th-century mountain community that offers a glimpse into Appalachian life.
Evening
Dine at Charlotte's Hoagie Shop, which offers a variety of hearty sandwiches perfect for refueling after a day of exploration. Spend your evening relaxing at your boutique B&B or take a leisurely walk around the charming town.
Bedtime
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Equestrian Adventures at Kentucky Horse Park
Morning
Lexington Horse Farm Tour and Keeneland Race Track Visit: Start your day with an immersive tour that includes visits to some of Lexington's most famous horse farms and the historic Keeneland Race Track. This tour provides an in-depth look at Kentucky's equestrian culture.
Afternoon
Farmwald's Restaurant & Bakery: Enjoy a delightful lunch at this highly-rated restaurant known for its homemade dishes and baked goods. After lunch, spend your afternoon exploring the Kentucky Horse Park itself, where you can visit various exhibits and watch live horse shows.
Evening
Bucky Bees BBQ: For dinner, indulge in some authentic Kentucky barbecue at this popular spot. End your evening with a relaxing stroll around the park or enjoy some local entertainment.
Bedtime
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4.90Lexington Horse Farm Tour and Keeneland Race Track Visit
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4.90Lexington Horse Farm Tour and Keeneland Race Track Visit
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Bourbon Trail: A Taste of Kentucky's Finest
Morning
Lexington Distillery District Food, Drink, and History Tour: Begin your day with an exciting tour that takes you through Lexington's Distillery District. Learn about the history of bourbon production while sampling some of the finest spirits.
Afternoon
Doc Crow's Southern Smokehouse & Raw Bar: Head to this renowned restaurant for lunch, where you can enjoy Southern-style barbecue and fresh seafood. Continue your Bourbon Trail adventure by visiting some of the famous distilleries in the area such as Maker’s Mark or Woodford Reserve.
Evening
The Silver Dollar: Conclude your trip with dinner at this highly-rated restaurant known for its creative dishes and extensive bourbon selection. Reflect on your journey through Kentucky as you savor one last taste of local cuisine before heading back to Ashburn.
Bedtime
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5.00Lexington Distillery District Food, Drink, and History Tour
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5.00Lexington Distillery District Food, Drink, and History Tour
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