Join Best of Times Travel as we 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 Nasvhille, TN all in one trip! 

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 us on this week long journey.  If you have never experienced this part of the country you owe it to yourself to make this trip.  We’ll visit the horse farm that brought us Secretariat, tour and taste fantastic bourbon distilleries, see the beginning of the Appalachian trail, 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.   

See the Day to Day Itinerary listed further down this webpage for details on the locations we visit during this amazing tour.  In the meantime here are some short video clips of some of the locations we will visit.

Louisville Slugger Museum Click Here

Buffalo Trace Distillery Click Here

Claiborne Farm Click Here

Great Smoky Mountains National Park Click Here

The Grand Ole Opry Click Here

The Country Music Hall of Fame Click Here

Here's What's Included as part of your Best of Times Travel EXCLUSIVE Package:

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

• 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, & 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 Jim Bean Distillery with tasting included

• Touring in Nashville to Include - Wildhorse 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

• Best of Times Travel Tour Director throughout trip
• Gratuities for Airport Transfers and Best of Times Travel Tour Director
• Optional Travelers Insurance by Chubb is offered - Click Here for Details on Chubb Travel Insurance Program 

ALL PRICES ARE PER PERSON AND ARE BASED ON DOUBLE OCCUPANCY.  IF YOU ARE A SOLO TRAVELER, PLEASE MAKE SURE YOU SELECT THE OPTION FOR SOLO TRAVELERS WHEN CHOOSING YOUR ROOM.  IF YOU ARE LOOKING FOR TRIPLE OR QUAD OCCUPANCY PRICING PLEASE CONTACT OUR OFFICE DIRECTLY.

Enjoy all of the amenities you have come to expect from a Luxury Hotel Property.  

Traditional View Rooms - Our Traditional View sleeping room at our hotel in Nashville features:   

Size: 350 square feet 

• King and Queen/Queen beds available with pillow top mattress and luxurious linens
• Lounge chair (King Room Only)
• Small refrigerator
• Work station with ample lighting
• 37-inch flat panel television
• Wired/wireless high-speed Internet access (for a fee)
• Cable and satellite television
• Two-line phones, speakerphone and voice mail
• In-room safe
• Movies/videos (for a fee)
• Coffee maker/tea service
• ADA compliant available

Atrium View Rooms -  Atrium View sleeping rooms overlook the lush indoor gardens or Delta River Section of the Resort. This room features:

Size: 350 square feet

• King and Queen/Queen beds available with pillow top mattress and luxurious linens
• Balcony, patio or bay window overlooking one of 3 atriums
• Lounge chair (King Room Only)
• Small refrigerator
• Work station with ample lighting
• 37-inch flat panel television
• Wired/wireless high-speed Internet access (for a fee)
• Cable and satellite television
• In-room safe
• Coffee maker/tea service
• ADA compliant available

For Full Details Regarding the Optional Chubb Travel Insurance Click Here.

Rates and itineraries shown here were in effect at the time of printing and no changes are anticipated; however, Best of Times Travel reserves the right to withdraw any tour or to make any rate changes, as necessary. Prices are subject to change. A deposit is always required to confirm a reservation. A Deposit of $500pp, plus insurance premium (if elected) is due upon registration to confirm your reservation. Travel Insurance: We recommend your purchase of optional travel insurance. This optional travel insurance is per person and the premium is based on the overall trip cost. Travelers MUST purchase the plan at the time of initial deposit. Coverage will not be in place unless your full Deposit is received. Cancellation schedule and fees are in place regardless of cancellation reason (including, but not limited to, force majeure, health pandemics or government restrictions). Travel Insurance Premium is also Non-Refundable regardless of cancellation reason. Payment in full must be received by July 21st, 2023 or this may result in an automatic cancellation. Please note: All cancellations must be made in writing and sent to Best of Times Travel. The date of cancellation is deemed to be the date received by Best of Times Travel. Cancellation Charges for this programs are as follows: Cancellations from 6/1/23 - 7/21/2023 will be assessed a $200 cancellation fee. Cancellations from 7/22/23 until 8/21/23 will be assessed a cancellation fee of 75% of the total fare. Cancellations after 8/21/23 will receive no refund, 100% of total fare. Best of Times Travel is not responsible for any refunds over and above said amount. Best of Times Travel reserves the right to issue any refunds, in whole or in part, in the form of future travel credit. 

 *Pre-Existing Medical Condition Exclusion Waiver has the following stipulations: plan must be purchased within 15 days of initial trip payment, insured must be medically able to travel at time of purchasing the plan, all pre-paid, non-refundable trip costs need to be insured.  This information is a brief description of the features of this insurance program. Coverage & pricing may vary by state. The provision of this document is for informational purposes only and is not an insurance contract. Coverage is being marketed by Chubb Insurance Solutions Agency, Inc. located at 202 Halls Mills Road, Whitehouse Station, New Jersey 08889. Insurance benefits are underwritten by ACE Property & Casualty Insurance Company located at 436 Walnut Street, Philadelphia, Pennsylvania 19106. 

Please note that a valid government issued photo ID such as a Passport, Passport Card, or Real ID drivers license is required for this trip, and must be valid for 90 days AFTER the date this trip returns.  *BEFORE BOOKING, PLEASE ENSURE THAT YOU PROVIDE YOUR LEGAL NAME AND DATE OF BIRTH AS THEY APPEAR ON YOUR PHOTO ID.  Errors in passenger information can result in your being denied boarding privileges. 

Today we depart from Boston, MA and fly to Louisville, KY to begin our adventure of  the Kentucky Bluegrass, the Bourbon Trail.  Upon arrival we will get acclimated with Louisville as we visit the heart of the city where the Bourbon trail begins.  The city boasts the world’s only, city-wide trail filled with award-winning micro-distilleries, exhibits and craft cocktail destinations.  We’ll enjoy lunch on our own on Fourth Street Live - Louisville’s entertainment, food, and retail hub in the city.  Then it’s onto one of the greatest influences on America’s sport, baseball, and see first hand the product that propelled legends such as Babe Ruth, Roberto Clemente and Cool Papa Bell. We’ll visit and tour the Louisville Slugger Factory.  On our tour you’ll be transported to the forests and mills where every Louisville Slugger bat begins, walk through the heart of the factory production line, check out never-before-seen steps in the bat-making process including the creation of fan favorite mini-bats, and receive a souvenir mini-bat.  Of course one can’t mention Louisville Kentucky without breathing the words Home of the Kentucky Derby - Churchill Downs.  Horse racing in Kentucky dates back to 1789, when the first race course was constructed in Lexington. Almost 100 years later, in 1875, Churchill Downs officially opened its gates in Louisville, and began its tradition as “Home of the Kentucky Derby” and the longest continually running sporting event in America.  We will seeing this legendary race track up close and personal with a visit to not only the Kentucky Derby Museum but we will also partake in a fantastic walking tour of the grounds.  This evening enjoy our comfortable hotel accommodations at the Drury Hotel along with a delicious dinner experience. (D)  

After our full breakfast at the hotel we make our way into the countryside past rolling green hills, horse pastures, and stroll onto the Bourbon Trail.  Our first stop will be Buffalo Trace Distillery - Over 200 years of fine bourbon craftsmanship make Buffalo Trace the World’s Most Decorated Distillery.  On our visit here learn about the history of Buffalo Trace Distillery and walk amidst the path of rolling bourbon barrels. You will be captivated by the alluring smell and atmosphere of bourbon sleeping inside the aging warehouses. Then you will go inside the renowned Blanton’s Bottling Hall where you will see signature bourbons being filled, sealed, labeled, and packaged—all by hand.  Of course the tour includes a tasting of some of their award-winning products and we’ll have time to visit the gift shop where unique gifts can only be found on-site.  Our second distillery tour will be the world renowned Woodford Reserve.  Our tour provides a guided education through the distillery that explains the history of bourbon, how Woodford is unique at all five sources of flavor, the bottling process, and much more. At the end of the tour enjoy a taste of their award-winning craft bourbon.  We will visit one more distillery today to round out the tour of the Bourbon Trail.  Lunch will be on our own today as we make our way through the country roads of Kentucky.  Tonight dinner is included and enjoy our hotel accommodations in Lexington, KY. (B,D)

After our included breakfast at the hotel we depart for touring. In the heart of Horse Country, among the rolling fields of bluegrass, limestone rich soil, and miles of plank board fences... lies an acreage of land steeped in tradition.  From world-class stallions, to breed-shaping broodmares, to legends of the turf..f​ew farms can match the majesty, the history, and the storybook success of world famous Claiborne Farm.  Come see and learn for yourself why Claiborne is known as one of the most iconic thoroughbred breeding farms in Kentucky’s Horse Country! Our tour includes a fascinating overview of Claiborne’s storied history, including its involvement with Triple Crown winner Secretariat. See where the legend is buried, and walk the grounds where many other famous racehorses called home.  From here we make our way south towards Gatlinburg, TN and the home of the Great Smoky Mountains National Forest.  But on the way we’ll first make a stop in Berea a historic college town and the arts and crafts center of KY.  Lunch is included this afternoon in Berea.  Enjoy the sights along the way as we travel through Daniel Boone National Forest and see the incredible landscape before us.  Then welcome to Gatlinburg, TN!  Tonight we’ll dine downtown at Blake Shelton’s famous restaurant - Ole Red for some food and country music.  Our accommodations are located in downtown Gatlinburg, TN within walking distance to all of the attractions in Gatlinburg. (B,L,D)

After our included breakfast at the hotel we head out to tour Great Smoky Mountain National Park.  Learn about one of the most diverse ecosystems on earth and the largest deciduous forest on the East Coast of the U.S.  We’ll make stops at multiple lookouts including the famous Newfound Gap to where you see both the TN and NC sides, stand in 2 states at the same time, and see the start of the Appalachian Trail that runs 1,972 miles up to Maine.  We’ll make our way back into downtown Gatlinburg where we enjoy Anakeesta.  Your ticket will include Anakeesta’s Chondola ride, Ridge Rambler vehicle ride, elevated 16-bridge Treetop Skywalk, Treehouse Village Adventure, Vista Gardens Walk, Memorial Forest Walk with interpretive signs, shopping and dining opportunities at Firefly Village, and the most gorgeous scenic views in all of Gatlinburg.  Lunch is on our own and dining at the top is truly fantastic.  Enjoy your afternoon and evening at your own pace in Gatlinburg.  With sights such as the Aerial Tram, the sky bridge, over 500 Shops, 100 restaurants, and 40 plus attractions there’s plenty to do.  Getting around can’t be easier either with Gatlinburg’s public trolley system.  For those that want we will make our bus available to take you to Dollywood, Dolly Parton’s Smoky Mountain theme park. (B)

Enjoy our breakfast at the hotel before we bid farewell to Gatlinburg and make our way to the Music Capital of the U.S. Nashville, TN.  On our journey we will make a stop to experience the world’s # 1 Bourbon at the Jack Daniel’s Distillery.  Crafting something that endures for over 150 years takes time and character. You’ll find plenty of both in the people and history that make Jack Daniel’s. Let one of Jack Daniel’s seasoned storytellers guide you through Mr. Jack’s distillery and old-time Tennessee whiskey-making process on our included guided tour. Then, finish your trip here with a memorable stop at the historic Barrel House 1-14. Here, you’ll linger over and sip five of the most popular whiskeys and liqueurs. We allow plenty of time  to shop for souvenirs.  Lunch will be on our own today.  Then it’s onto our lodging for the next 2 Nights at the finest in Southern hospitality - the opulent Gaylord Opryland Resort. This evening we head out for Nashville’s # 1 Dining and Entertainment destination - the famous Wildhorse Saloon.  More than 1.5 million music lovers stampede through their doors annually to catch the hottest in live entertainment, learn the newest dance steps and dine on their award-winning Southern smokehouse cuisine.  Enjoy a fabulous evening out on the town. (B,D)     

Enjoy a fabulous Full Breakfast at the resort.  We then depart to enjoy a riding city tour to acclimate us to the wonderful sights of the area such as the State Capitol, Music Row and the Parthenon - a full scale replica of the Athenian original!  We will visit the cultural epicenter of the music city, Ryman Auditorium.  Most famous as the home of the Grand Ole Opry from 1943 - 1974, its history as Nashville’s premiere theater and central gathering place started even before construction was complete in 1892.  Enjoy lunch on your own along Honky Tonk row in downtown.  This afternoon enjoy our backstage tour of the Grand Ole Opry and walk out on the main stage!  You never know you just might run into one of the entertainers for the evening.  This evening we enjoy a terrific meal at one of the great steakhouses just minutes from the Opry.  After dinner we take in the nighttime performance from our reserved seats at the Grand Ole Opry. (B,D) 

Enjoy a fabulous Full Breakfast at the resort. Then pack up for our final day of touring.  Our first stop is the Country Music Hall of Fame to be explored at your own pace. The museum has an extensive, permanent objects collection. This collection includes more than eight hundred stage costumes, over six hundred instruments, and hundreds of other objects—from microphones to automobiles—documenting the history of country music. Included in our package is a visit to Historic RCA Studio B, for an up close look at Nashville’s oldest remaining record studio.  Enjoy lunch on your own at the Hall of Fame or take an easy stroll over to Honky Tonk Row for food, beverage, shopping and so much more with your free time.  Enjoy dinner on your own before we embark on our late afternoon or evening flight for home with incredible memories of a wonderful trip together! (B)