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Kentucky Bluegrass Bourbon Trail Smoky Mountains and Nashville


Sept. 23 – 29


From $3,899 PP



Journey into the heartland of America and visit the very best sights of Kentucky and Tennessee! This incredible 7-day trip features Louisville, KY, Churchill Downs, the infamous Bourbon Trail, Kentucky’s famous horse country, Gatlinburg, TN, the Great Smoky Mountains, and Nashville, TN!

7 Days

6 Nights


6 Breakfasts

1 Lunch

5 Dinners



About This Tour

BUCKET LIST TRIP | STAFF TOP PICK  The rolling fields of bluegrass, the majesty of horse farms, the great Smoky Mountains, the sweet taste of bourbon, and foot stomping sounds of country music await you. If you have never experienced this part of the country your owe it to yourself to make this trip.

*No Hassle Refunds​

No Booking Fee, *No Change Fees​

Traveling Well Safely

Top Rated Travel Protection

Book with Confidence

* With Insurance Purchased

Your Tour Includes

  • Roundtrip Air Transportation from Logan Airport 

  • 1 Night Lodging in Louisville, KY 

  • 1 Night Lodging in Lexington, KY 

  • Tours in Louisville/Lexington, KY – including Churchill Downs, Louisville Slugger Factory, the Oldest Continuously Operating Distillery in America (Buffalo Trace), 2 More Distilleries, Horse Farm Tour, and more. 

  • 2 Nights Lodging in the Mountain Resort Town – Gatlinburg, TN 

  • Touring for Gatlinburg Area – Travel through Daniel Boone National Forest, Tour Great Smoky Mountain National Park, Gatlinburg TN, Option to see Dollywood (Dolly Parton’s Smoky Mountain Theme Park) 

  • 2 Nights Lodging at the Opulent Gaylord Opryland Hotel – Nashville, TN 

  • Tour of Jack Daniel’s Distillery with tasting included 

  • Touring in Nashville to Include – Wild Horse Saloon, Guided City Tour, Ryman Auditorium, Backstage Tour of the Grand Ole Opry, the Country Music Hall of Fame, RCA Studio B, and Show at the Grand Ole Opry 

  • 12 Meals – 6 Breakfasts, 1 Lunch, 5 Dinners 

  • Luggage Handling Fees – with the exception of airline imposed luggage fees 

  • Services of a Best of Times Travel Tour Director Throughout Your Trip (gratuity included) 

  • Optional Travelers Insurance by Chubb Travel Protection is Available

  • Roundtrip Transfers to Logan Airport with hometown pick-up guarantee


We’ll visit the horse farm that brought us Secretariat. Click HERE for a video on Claiborne Farm, tour and taste fantastic bourbon distilleries. Click HERE for a visit to Buffalo Trace Distillery.  See the beginning of the Appalachian trail, Click HERE for a video on the Smoky Mountains, and take in all that Nashville offers including a show at the Grand Ole Opry. Great Tours, Great Accommodations, Great Company – This is a trip that will leave you with memories of a lifetime.

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Plan Your Group Trip Today!

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