Music City to Windy City
Tour Duration 15 Nights - From £3149*
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Windy City to Music City – The Ultimate American Music Tour!

DAY BY DAY TOUR ITINERARY
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Welcome to our all-new Windy City to Music City Tour! Your Ultimate American Music Tour is about to begin. After you’ve checked into your Chicago hotel, feel free to join your guide and driver for a welcome meeting and a chance to meet your fellow travelers.
Today, your tour manager will guide you on a brief Chicago city tour. Starting at Navy Pier, you'll have the chance to hop on and off the bus at several points of interest. In the afternoon, we'll explore the historic Chess Records, then enjoy dinner and a night filled with entertainment at the city's amazing blues clubs!
This morning, as we leave Chicago behind, we’ll journey around Lake Michigan, making a stop in Gary, Indiana, to see the Jackson 5's childhood home. Afterward, we’ll head to Kalamazoo for some food and a visit to a local brewery before continuing on to Ann Arbor. Tonight, we’ll explore Main Street, enjoying great food and entertainment.
This morning, we’ll take a short trip to Detroit to visit “Hitsville U.S.A,” the iconic home of Motown Records. After exploring this amazing museum, we’ll make a quick stop at Woodlawn Cemetery to honour Aretha Franklin, Rosa Parks, and other Motown Musicians, before continuing the journey to Cleveland! This evening we'll take you downtown where, you'll be free to explore at leisure.
This morning after a leisurely breakfast, we will visit one of Cleveland’s top attractions - The Rock & Roll Hall of Fame and Museum. After our visit to this iconic building, join us on a short driving tour of the City’s lakeside districts followed by free time to explore this fascinating city at your own pace. This vibrant city is home to arts, culture, and landmarks that pay homage to the history of music. Made up of "Districts" like Cleveland Heights, Little Italy, Shaker Square, Downtown and filled with world-class theatre, live music and noteworthy nightlife there is so much to see and do in Cleveland!
Travelling south into Kentucky we'll reach Louisville - home of the famous "Slugger" Kentucky's largest city sits on the Ohio River along the Indiana border. We will spend the evening downtown enjoying dinner and local entertainment.
This morning, we’ll visit the Muhammad Ali Center, dedicated to the legendary boxer and Louisville native. Afterward, you’ll have free time to explore the museums and landmarks that make Louisville famous. For instance, baseball is celebrated at the Louisville Slugger Museum and Factory, where Major League bats are crafted, and a giant baseball bat marks the entrance. Later, we’ll take a short trip to Owensboro, home to the Bluegrass Museum and more!
The day starts with a visit to the Bluegrass Museum, followed by a trip to Central City to explore the Everly Brothers Museum. Afterward, we'll head to Memphis, check in to our hotel, and you'll have free time to enjoy everything Beale Street has to offer.
After breakfast today, we’ll explore the story of the Million Dollar Quartet at Sun Studio and honour the King of Rock & Roll, Elvis Presley, with a visit to his iconic home, Graceland Mansion. Next, we’ll take a brief driving tour of the city, including a photo stop at the historic Lorraine Motel. This evening, enjoy some free time to perhaps savour some Memphis BBQ and soak in the cool blues vibes on Beale Street!
A two hour journey this morning will take us to our next stop - Muscle Shoals Alabama - America's best kept secret is known as the Hit Recording Capital of the World with good reason. During our time here we'll tour some of the amazing Studio's enjoy live music, learn about Alabama's famous musicians and perhaps meet a few as we travel around the area.
A round-trip today will take us from the Muscle Shoals area into Mississippi to visit Tupelo, the birthplace of Elvis Presley, followed by a stop in Red Bay, Alabama, home of country music superstar Tammy Wynette. We'll end the day back in the Shoals for some live music at the Rattlesnake Saloon—a venue like no other!
Discover more music and fun today as we explore Muscle Shoals, Alabama—an area packed with surprising finds. We'll visit Ivy Green, the childhood home of Helen Keller, and The WC Handy Home, where the Father of the Blues began his journey. Later, we'll enjoy another night of live local music.
Before leaving the Muscle Shoals area this morning, we’ll spend a couple of hours at the Alabama Music Hall of Fame—you’ll be amazed by how many famous musicians hail from Alabama. You might have even crossed paths with some of them during your stay. Afterward, we’ll head back to Music City—Nashville, Tennessee—where you’ll have plenty of free time to explore this fantastic city.
Today, you have the option to join us on a trip to Southern Kentucky. Our first stop is the charming small town of Franklin, featuring a beautiful courtyard square. Discover why Country Legends Johnny Cash and June Carter chose this spot to tie the knot, and enjoy lunch at the Mennonite Community! In the afternoon, we’ll take a short drive to Hendersonville, Tennessee, where Johnny and June lived at the Lake House. Explore its history and visit their final resting place to pay your respects. Later, enjoy free time and the vibrant music scene around Nashville. In the Opryland area, you can take a relaxing cruise on the General Jackson Showboat, explore the Opryland Hotel, or stop by some of the famous honkytonks. Don’t miss the nearby Nashville Palace for great food and live music. You’ll also find shopping, restaurants, and Madame Tussaud's at Opry Mills!
On your last day in Nashville - be sure to visit the wonderful Centennial and Bi-Centennial Parks and a visit to the Parthenon is a must. Make sure you buy your cowboy boots on Lower Broadway and kick your heels on Printers Alley tonight - before getting ready to make your onward journey tomorrow.
Sad but true - your tour comes to an end today! Your tour manager will escort you to Nashville International Airport for your return/onward flight.
We hope you have enjoyed your time with us and that we see you on another Travelling Time Tour soon!
DEPARTURE: 2026 SOLD OUT!

SCHEDULED DEPARTURE DATES
Our Music City to Windy City Escorted Group Tours are scheduled to depart:
2026 Sold Out! New Dates Coming Soon!
If these dates are not suitable, please call us on 01738 643737 to discuss our small group option.
BOOKING INFORMATION
At Travelling Time we offer exceptional value for money on our fixed price escorted tours. We include transportation to suit your group size, hotel accommodation, meals as described and all attractions listed in our itineraries.
FLIGHT INCLUSIVE PACKAGES






