9-Nights Bluegrass & Bourbon Trail Road Trip from $1,589

Day 1: Arrive in Memphis

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Arrive at Memphis International Airport and pick up your car rental. Depending on your time of arrival you might have time to explore the birthplace of the blues by taking in a performance in one of the entertaining Beale Street blues bars. Memphis offers a multitude of musical and movie moments, and there are two nights to explore your favorites. Start with a visit to Graceland, home of the late Elvis Presley, then choose between the Rock & Soul Museum, the Stax Museum of American Soul Music, the Gibson Guitar Factory, or Sun Studio where musicians such as B.B. King, Elvis Presley, and Jerry Lee Lewis recorded their rock’n’roll hits (all optional visits). Overnight Memphis.

Hotel: Crowne Plaza Memphis Downtown (3 Star Rating)

Embrace the culture and music roots of Memphis at the Crowne Plaza Memphis Downtown. Our modern hotel is across from the Renasant Convention Center and a mile from the Beale Street Entertainment District and St. Jude Children’s Research Hospital. Ride our free shuttle to downtown Memphis attractions like AutoZone Park and FedEx Forum, or enjoy live music and famous BBQ joints. We are only 20 minutes from the Memphis Zoo and Graceland.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Memphis combines the charm of the Old South with the exciting pace of a modern metropolis. During your stay, may we suggest an optional visit to any outdoor concerts at the Mud Island outdoor amphitheater. Located right on the Mississippi River, Mud Island River Park is a historic and scenic outdoor area. Or dine in B.B. King’s restaurant on famous Beale Street. Overnight Memphis.

Hotel: Best Western Inn (3 Star Rating)

At this Winchester hotel, they put the comfort of our guests first and understand that a great vacation depends on hospitality, great accommodations, and friendly service.

Nearby the Winchester hotel, guests can find Winchester Industrial Park and Tims Ford State Park. However, if you're in town to tour the campus of the University of the South in Sewanee, TN, you'll find that you're just a short drive away. Alumni weekends, homecoming, and graduation always bring guests to our hotel, and we're happy to host you during your stay.

Convenient to the local industry, the Winchester hotel is in the ideal location for business and leisure travelers alike. This hotel is located near the Jack Daniel's Distillery and the George Dickel Distilleries, both favorite attractions. Friendly staff members are happy to provide you with recommendations during your stay.

High on the Hog, Bear Trace Golf Course, or boating, skiing, and fishing at Tims Ford State Park are all great ways to spend your vacation. The Jack Daniel's Barbecue Cook-off is a delicious, family-friendly event where you can sample the best barbecue in Tennessee. A few short minutes from Manchester Farm, host to the Bonnaroo® Music Fest, only 20 minutes from the Circle E Guest Ranch and 30 to The Caverns Music Venue.

At the Winchester hotel, they also regularly host business travelers like employees of Nissan, CST, and Tepro. They offer superior customer service along with ultra-clean rooms and a free hot breakfast. Enjoy a daily hot buffet of eggs, meats, waffles and pastries, fresh fruits, yogurts, biscuits and gravy, and a selection of cereal hot and cold, juice and coffee.

With a variety of room types to choose from, it doesn't matter if you're here for business alone or traveling with the entire family. We're committed to making your stay as comfortable and enjoyable as possible.

Reserve a comfortable room at Best Western Inn to set the foundation for a fantastic trip! Enjoy your stay.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Continue your exploration to Lynchburg where you will pass out of the country music for the home of Bourbon. You will discover the famous home of the Jack Daniel’s whiskey distillery during your stay. While touring the Jack Daniel’s Distillery (optional), learn about the great American wonder of the Cave Spring Hollow, and discover more about the history of the distillery. Don’t miss Nina’s Taste of Tennessee and indulge in the sweet treats and surprises that this quaint shop has to offer. Many of her sweet treats are made with a variety of Jack Daniel’s whiskey. Overnight Lynchburg.

Hotel: Best Western Inn (3 Star Rating)

At this Winchester hotel, they put the comfort of our guests first and understand that a great vacation depends on hospitality, great accommodations, and friendly service.

Nearby the Winchester hotel, guests can find Winchester Industrial Park and Tims Ford State Park. However, if you're in town to tour the campus of the University of the South in Sewanee, TN, you'll find that you're just a short drive away. Alumni weekends, homecoming, and graduation always bring guests to our hotel, and we're happy to host you during your stay.

Convenient to the local industry, the Winchester hotel is in the ideal location for business and leisure travelers alike. This hotel is located near the Jack Daniel's Distillery and the George Dickel Distilleries, both favorite attractions. Friendly staff members are happy to provide you with recommendations during your stay.

High on the Hog, Bear Trace Golf Course, or boating, skiing, and fishing at Tims Ford State Park are all great ways to spend your vacation. The Jack Daniel's Barbecue Cook-off is a delicious, family-friendly event where you can sample the best barbecue in Tennessee. A few short minutes from Manchester Farm, host to the Bonnaroo® Music Fest, only 20 minutes from the Circle E Guest Ranch and 30 to The Caverns Music Venue.

At the Winchester hotel, they also regularly host business travelers like employees of Nissan, CST, and Tepro. They offer superior customer service along with ultra-clean rooms and a free hot breakfast. Enjoy a daily hot buffet of eggs, meats, waffles and pastries, fresh fruits, yogurts, biscuits and gravy, and a selection of cereal hot and cold, juice and coffee.

With a variety of room types to choose from, it doesn't matter if you're here for business alone or traveling with the entire family. We're committed to making your stay as comfortable and enjoyable as possible.

Reserve a comfortable room at Best Western Inn to set the foundation for a fantastic trip! Enjoy your stay.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Venture into the 4th largest city in Southeast Tennessee and taste the South's favorite snack food, the Moon Pie, which originated in Chattanooga in the early 1900s. The city has received national recognition for the renaissance of its beautiful downtown and expansion of its riverfront. A must visit is the Chattanooga Choo Choo Train Station, an iconic place that has been turned into a hotel. The station was first built in the historic district in 1908. Summer travelers should check the dates of the annual Chattanooga Riverbend Festival. Overnight Chattanooga.

Hotel: Days Inn by Wyndham Chattanooga/Hamilton Place (2 Star Rating)

Just off I-75 and only 4 miles from the Chattanooga International Airport, our Days Inn Chattanooga/Hamilton Place hotel is your place for a sunny stay in the Chattanooga area. Whether you are our guest for just one night or an extended stay, we offer comfortable accommodations at a great price.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Make your way north to Gatlinburg and pass through the rich culture and natural beauty of Knoxville, which has the perfect blend of southern hospitality and modern development. Start off your day by taking a scenic hike in the Great Smoky Mountains National Park with plentiful trails and beautiful surroundings. Visit the Sugarlands Distilling Company (optional), where you can enjoy the varieties of samples they offer. Or choose to visit the Smoky Mountain Brewery and have a quick lunch (optional). Afterwards, stroll through the downtown Village Shops and enjoy the beautiful architecture while doing a little shopping with an abundance of restaurants to choose from. Overnight Gatlinburg.

Hotel: River Terrace Resort and Convention Center (2 Star Rating)

River Terrace Resort and Convention Center offers comfortable accommodations in the heart of Downtown Gatlinburg, Tennessee. You’re minutes from Great Smoky Mountains National Park, the most-visited national park in the United States. Enjoy easy access to Gatlinburg’s main street, exciting outdoor activities, and Dollywood theme park. We’ll help you discover all that Gatlinburg, Tennessee has to offer.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

As you leave Gatlinburg and make your way through Kentucky, enjoy the marvellous scenery of the Appalachian Mountains and the Mississippi River, with the Ohio River forming a northern boundary. Begin the morning in the Horse Capital of the World, located in the heart of Kentucky's Bluegrass Region and explore the rugged terrain of the Daniel Boone National Forest, named after the fearless legendary American pioneer. Also located in the Daniel Boone National Forest is Cumberland Falls, a majestic 120-foot wide, 67-foot-tall waterfall. Overnight Lexington.

Hotel: Hilton Garden Inn Lexington Hamburg (3 Star Rating)

We’re off I-75, one mile from Hamburg Pavilion, and within walking distance to several restaurants. The University of Kentucky can be reached in 20 minutes, and Keeneland Race Course and Kentucky Horse Park are 14 miles from our door. Our restaurant serves breakfast and dinner, and our 24-hour Pavilion Pantry is stocked with snacks and travel essentials. We also feature a heated indoor pool, fitness center, and free WiFi.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

The drive today to Louisville, passes by numerous small towns and luscious green fields. As you reach Louisville, don't forget to visit the home of the world's most famous thoroughbred horserace, the Kentucky Derby which takes place at Churchill Downs the first Saturday each May. Don't forget to bring a beautiful hat for the occasion. Featured in the movie Sea Biscuit, Churchill Downs is the mecca of American horse racing and home of the Kentucky Derby Museum. Take a short side trip to Bardstown and visit My Old Kentucky Home State Park, the inspiration for Stephen Foster's anthem of the same name which is sung by the crowds every year at the Kentucky Derby. Baseball fans should ensure they fit in a visit to the Louisville Slugger Museum, an interactive museum honoring some of baseball's greats. Overnight Louisville.

Hotel: Drury Inn & Suites Louisville North (3 Star Rating)

Located at I-265 and Brownsboro Road, Drury Inn & Suites Louisville North is close to local shopping and businesses and just 13 miles from downtown Louisville, the hotel is perfect for business or leisure travelers. Enjoy free hot breakfast and free hot food and cold beverages at our evening 5:30 Kickback®.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Nashville, 'Music City USA', is your fabulous music destination today. Make your way over to the Music City Walk of Fame honoring the top country performers. It's a multimedia music shrine including movie theatres, costumes, instruments, and other artifacts detailing country music's colorful history. Consider a visit to the Ryman Auditorium and a night at the Grand Ole Opry. Overnight Nashville.

Hotel: Hutton Hotel (4 Star Rating)

Hutton Hotel pulses with creative energy and Southern charm. Inside, 250 guestrooms and suites showcase plush bedding, granite bathrooms with rainfall showers, and floor-to-ceiling windows revealing sweeping city views. Suites extend comfort further with living areas, full kitchens, and elegant design touches. The property’s heart is Analog, a 5,000?sq?ft live music venue woven seamlessly into the lobby, while two custom Writers’ Rooms invite guests to compose in studio-grade surroundings. WestEnd Kitchen + Bar elevates Southern cuisine within a stylish setting. Warm hospitality and a spirited ambiance make Hutton equal parts refuge and stage.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Today we suggest a visit to the Opry Mills shopping Center or take a stroll through the Music Valley's Wax Museum of the Stars and witness life-size wax figures of many country music stars. For history enthusiasts, The Tennessee State Capitol in downtown Nashville is one of the oldest working capitols in the United States and serves as home of the Tennessee General Assembly and houses the governor's office. The building, one of 12 state capitols that does not have a dome, was added to the National Register of Historic Places in 1970 and named a National Historic Landmark in 1971. Overnight Nashville.

Hotel: Hutton Hotel (4 Star Rating)

Hutton Hotel pulses with creative energy and Southern charm. Inside, 250 guestrooms and suites showcase plush bedding, granite bathrooms with rainfall showers, and floor-to-ceiling windows revealing sweeping city views. Suites extend comfort further with living areas, full kitchens, and elegant design touches. The property’s heart is Analog, a 5,000?sq?ft live music venue woven seamlessly into the lobby, while two custom Writers’ Rooms invite guests to compose in studio-grade surroundings. WestEnd Kitchen + Bar elevates Southern cuisine within a stylish setting. Warm hospitality and a spirited ambiance make Hutton equal parts refuge and stage.

Rental Car: Hertz - Memphis Intl Airportto Memphis Intl Airport

Depart the capital of country and western music to return to the home of the blues. Make your way to Memphis International Airport to check in for your flight home unless you plan to extend your stay in Tennessee.