Holiday Overview
Embark on a self-drive adventure from Chicago to Nashville, immersing yourself in the rich sounds of blues, country, and rock while savouring the flavours of bourbon.
Begin in Chicago, the birthplace of the blues, where the city’s legendary blues clubs bring the soulful sound to life. From there, journey through Kentucky, renowned for its bourbon. Follow Louisville’s Urban Bourbon Trail for a taste of the region's finest, then stop in Owensboro, the heart of bluegrass music.
Continue into Tennessee, starting with Memphis. Stroll along the iconic Beale Street, where blues, soul, and rock 'n' roll fill the air. Savor the city's famous Memphis BBQ before heading to Nashville.
In Nashville, the home of country music, visit the Country Music Hall of Fame to celebrate your favourite stars. Experience live music at the world-famous Grand Ole Opry and tour Graceland, the legendary home of Elvis Presley, to see his iconic outfits and more.
This unforgettable road trip offers the perfect blend of music and cuisine!
States Visited: Illinois, Kentucky & Tennessee
Chicago to Nashvile: Blues, Bourbon and Country includes:
- International Flights
- Car Hire
- 12 Nights Accommodation
Day 1 - UK to Chicago
Arrive in Chicago and transfer to your chosen hotel, spending the remainder of your day at leisure.
Featured accommodation
Palmer House a Hilton Hotel
Day 2 - Explore Chicago
A full day to explore the sights of Chicago.
Featured accommodation
Palmer House a Hilton Hotel
Day 3 - Chicago
Another full day to explore Chicago, why not ask your consultant about adding on one of our Chicago experiences.
Featured accommodation
Palmer House a Hilton Hotel
Unmissable Experiences
Chicago Experiences
Day 4 - Chicago to Louisville
Today pick up your car hire and begin your drive through Indiana to Louisville, Kentucky. Louisville is home to the Kentucky Derby and best known for its bourbon, we recommend following the popular Urban Bourbon Trail.
Featured accommodation
Brown Hotel
Day 5 - Louisville
Spend today exploring Louisville the city is filled with lots to explore including the Muhammad Ali Centre where you can learn about the life and legacy of this legendary boxer, or tour the Churchill Downs race track.
Featured accommodation
Brown Hotel
Day 6 - Louisville to Owensboro
Your drive today continues to Owensboro, the Bluegrass Capital of the world. Make a visit to the Bluegrass Music Hall of Fame to learn more about the heritage of this distinctive genre.
Featured accommodation
Best Western Plus Owensboro
Day 7 - Owensboro to Memphis
Continuing your music trail your drive today takes you to Memphis home to the blues, soul and rock’n’roll. Walk along Beale Street filled with music and savour at the delicious Memphis BBQ!
Featured accommodation
Sheraton Memphis Downtown Hotel
Day 8 - Memphis
A full day at leisure to explore the iconic sights of Memphis. Visit Sun Studio where a multitude of iconic artists have recorded including Elvis, visit Stax Museum of American Soul Music and end the night listening to local blues artists.
Featured accommodation
Sheraton Memphis Downtown Hotel
Day 9 - Memphis
Another full day to explore Memphis.
Featured accommodation
Sheraton Memphis Downtown Hotel
Day 10 - Memphis to Nashville
From one iconic music city to another, as you make your way to Nashville. On route Nashville make a stop at Graceland the home of Elvis, here you can view some of his iconic outfits and his pink Cadillac. Spending the remainder of your day at leisure in Nashville.
Featured accommodation
Inn at Opryland
Day 11 - Nashville
Nashville is renowned for its pivotal role in country music, and no visit would be complete without a stop at the legendary Bluebird Cafe, a famed venue where local songwriters perform original music. For an unforgettable experience, head to the Grand Ole Opry, the world’s longest-running radio show, where rising country stars and seasoned legends take the stage.
Dive deeper into Nashville's music legacy at the Country Music Hall of Fame and Museum, the largest museum in the world dedicated to music. This must-visit destination offers something for everyone, with a vast collection of artifacts from legendary country artists and special exhibits honouring your favourite stars, including the Taylor Swift Education Centre.
Another highlight is the Johnny Cash Museum. Here, visitors can explore Johnny Cash’s life and career through an extraordinary collection of rare historical documents, awards, costumes, and instruments, many of which have never been displayed before.
Featured accommodation
Inn at Opryland
Day 12 - Nashville
Another full day to explore Nashville, speak to your consultant if you wish to add one of our Nashville Experiences.
Featured accommodation
Inn at Opryland
Unmissable Experiences
Nashville Experiences
Day 13 - Nashville to UK
Today is your final day in Nashville, make your way to the airport returning your car hire before your onward flight home.
Palmer House a Hilton Hotel, Chicago
Palmer House® A Hilton Hotel has 140 years of experience, winning over downtown Chicago travelers with award-winning service. Set in the theatre and financial district, this landmark hotel is close to well-known attractions. You’ll find famous frescoes, stylish suites, massive meeting space and artful dining at Lockwood and Potter's Chicago Burger Bar. Relax at The Spa at Palmer House or work out in the sizeable fitness center.
Brown Hotel Louisville
An iconic destination inextricably woven into the fabric of the city, The Brown Hotel is opulent yet approachable – like a fine Kentucky bourbon that never overwhelms you with its history but instead entertains you with a lifetime of colourful stories.
Best Western Plus Owensboro
Quietly nestled in the heart of Owensboro, Kentucky the Best Western Plus Owensboro, is located off Bypass 60. Offering guests, a comfortable and relaxing stay. Explore the area’s historical sites like the Bluegrass Music Hall of Fame & Museum and Smothers Park.
Sheraton Memphis Downtown Hotel
Sheraton Memphis Downtown Hotel invites you to experience the best of the city with them. The hotel welcomes you with a terrific location, within walking distance of legendary Beale Street and close to Graceland; also directly connected to Memphis Cook Convention Center via skywalk. Large, intuitively designed rooms and suites boast complimentary Wi-Fi and the Sheraton Signature Sleep Experience. Many also offer views of the Mississippi River.
Image Gallery
Nashville, Broadway
Bluegrass Music Hall of Fame, Owensboro
Chicago River
Sun Studio, Memphis
Grand Ole Opry, Nashville
Millenium Park, Chicago
Chicago
Bluegrass Music
Louisville
Muhammad Ali Centre
Derby Dan Horse Farm, Lexington
Owensboro, BBQ
Beale Street, Memphis
Beale Street, Memphis
Graceland
Birthplace of Country Music
Jack Daniels Distillary
Country Music Hall of Fame, Nashville
Nashville
Alternative Holidays That May Interest You
Below you will find a small selection of 2025, 2026 holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 270 0009 and let one of our Holiday experts design the perfect trip for you
Pacific Coast Highway Road Trip
- Los Angeles
- Pismo Beach
- Monterey / Carmel
- Yosemite National Park
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- The exciting buzz of Los Angeles & Hollywood
- California's beautiful coastline
- The stunning natural beauty of Yosemite
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Canyon Adventure Fly Drive Holiday
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California Fly Drive
- San Francisco
- Sonoma
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Blues & Booze USA Road Trip
- Chicago
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- Louisville
- Nashville
- Memphis
- Vicksburg
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- Kentucky Bourbon Trail
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Best of New England Fly Drive
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
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- Visit beautiful maritime towns
- See the beautiful mountains of New Hampshire & Vermont
- Experience historic Boston
14 Nights from £3430pp
Talkin' Texan Self Drive Holiday
- Dallas
- Austin
- Fredericksburg
- Bandera
- San Antonio
- Corpus Christi
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12 Nights from £3459pp
