top of page

The Music Road

The legendary Music Road is an unforgettable journey from Chicago, passing by Nashville, Tennessee to New Orleans, Louisiana, with music around every corner. From the birthplaces of celebrated artists and vinyl record shops to recording venues and Southern culinary delights, every stop has a story to tell. What to bring: a harmonica to play along with the Blues, your favorite playlists and an appetite for southern culinary delights.



Trip Infos

  • Enjoy the best Jazz, Blues and Country Music cities in the country

  • Stay at Historic Hotels and dine at Historic Diners

  • Celebrate Jazz in Chicago at an intimate Diner Show 

  • Enjoy a private walking Country Music tour in Nashville 

  • Tour Memphis in style with a private vintage Cadillac 

  • Drive the Blues Highway along the Mississippi River 

  • Enjoy a Private Jazz Tour New Orleans with a Musician guide

Duration:  15 Days / 14 Nights 


  • Day 1-3: Chicago - LondonHouse

  • Day 3-4: St Louis - Live By Loews 

  • Day 4-6: Nashville - Bobby Hotel

  • Day 6-8: Memphis - Arrive Hotel

  • Day 8-9: Clarksdale - Shack Up Inn 

  • Day 9-10: Vicksburg - Oak Hall 

  • Day 10-11: Natchez - Monmouth Historic Inn

  • Day 11-13: New Orleans - One11 Hotel

Estimated Price:  $3,800 per person

(Based on 2 Adults / Mix of Private & Shared Activities)

Image by Sawyer Bengtson


Welcome to Chicago ! Upon arrival, pick-up tour car rental and drive to your hotel. 

There it is: the famous Chicago skyline set against the sweeping shore of Lake Michigan. You’ll quickly appreciate this urban-meets-natural beauty when your feet hit the ground in the nation’s third-largest city. In the heart of the Midwest, Chicago boasts soaring skyscrapers, 77 colorful neighborhoods, 42 kilometers of lakefront with 26 beaches and 580 parks and green spaces. Equally impressive are the dining options – 7,300 restaurants and more than 65 craft breweries – outstanding arts and culture, urban recreation along the waterfront, world-famous events and a vibrant LGBTQ+ scene. 

Night at: The LondonHouse - Riverview King 

Image by Chris Bair


After a day at leisure exploring the city, enjoy an intimate Jazz venue at le Piano.

Le Piano is truly a hidden gem with Bohemian Parisian influences, tucked away in the Rogers Park neighborhood. With a listening room designed around a magnificent grand piano where intimate performances are featured every evening by Chicago’s finest jazz musicians, it is an experience quite like no other. Special guest appearances include different artists every day from all over the world

Night at: The LondonHouse - Riverview King 



Today, take the Route 66, heading south direction of St Louis. 

Travelers looking for cosmopolitan fun, excitement and adventure will discover a great fit in St. Louis. Located in the midwestern USA, St. Louis is sophisticated yet affordable with a variety of attractions, exhibits and cuisine, all wrapped in a friendly, diverse atmosphere

Night at: Live By Loews - King  



On the road again to THE music city in the USA; Nashville. Of course, music remains Nashville’s calling card to the world and is the very heart of the city. Long recognized as the world’s capital of country music, Music City's sounds also include pop, rock, gospel, Americana, bluegrass, jazz, classical, contemporary Christian, blues and soul. With more than 120 live music venues across the city, there is something for everyone. You’ll catch pickers and songwriters all over town, in places like bluegrass venue Station Inn, the rock venue Exit/In, the honky-tonks on Broadway, the song-centered Bluebird Cafe or the legendary Ryman Auditorium.

Night at: Bobby Hotel - King 

Image by Tim Mossholder


This Morning, meet your guide and let him show you why Nashville is called Music City.

Hank, Johnny, Chet, Patsy, George, Tammy, Conway, Loretta, Dolly, Merle, Willie … there was a time when country music was on a first name basis with its fans. A time when the streets of downtown Nashville were alive with the sound of backroom guitar pulls, midnight jamborees and the Grand Ole Opry.

Now you can recapture the magic of this golden era on the Walkin’ Nashville Music City Legends Tour. Packed with history, fun trivia and behind-the-scenes anecdotes about your favorite country legends, this two-hour walking tour is designed for music lovers who want to know the real story of how Nashville came to be called Music City.

Night at: Bobby Hotel - King  



Today, drive to an other World famous city Music. The City of the King; Memphis !

From a blues club on Beale Street to some of the greatest barbecue in the world, a visit to Memphis will touch all the senses. Memphis is where blues music grew up, where rock ‘n’ roll was born and where important strides were made in the struggle for civil rights, set to the beat of the city's soul music explosion. This living history hits visitors right away during a stroll through Graceland, Elvis Presley’s final home, or on a visit to the National Civil Rights Museum, located at the site where Martin Luther King Jr. lost his life.

Night at: Arrive Hotel - King 



This Morning, meet your guide and ride in style in Memphis's street in an vintage convertible car. 

Explore the famous sights and sounds that put Memphis on the map. Go back in time and inhabit a world that changed the course of history. See how Memphis has evolved since the early 1800's,  from its thriving cotton industry to an epidemic that almost wiped it off the map. Explore where music pioneers created a sound that had a global impact and stand on the sacred ground where the civil rights movement was rocked to its core.  Includes stops at Memphis' most famous recording studios, the National Civil Rights Museum,  historic parks, churches, music venues and much more.

Night at: Arrive Hotel - King 



Time to take the road again, follow the music on the blues highway, you just arrived in the most fun place of all; the Shack up inn of Clarksdale. 

Host to musical greats like Muddy Waters and Bukka White, Clarksdale is a must-see for any Blues fan. Make time for the Delta Blues Museum, which recounts the history of the Blues and has musical instruments, costumes and other memorabilia. It even features Muddy Waters former home. Spend the night at the iconic Riverside Hotel, where several prominent Blues musicians have stayed. Don't miss the New Roxy where superstar, Soul Music pioneer and Clarksdale native Sam Cooke performed along with other famous musicians. On the way out, be sure to check out the iconic sign at the Crossroads, where local lore says Robert Johnson made a deal with the devil to play Blues that well.

Night at: Shack Up Inn - Shack Cabin



Back on the Road along the Mississippi River. The South is the birthplace of the blues, and Mississippi played a large role in the genre's development. To honor this rich musical heritage, The Mississippi Blues Foundation created the Mississippi Blues Trail with a series of markers that commemorate significant people, places and more. Home to six Blues Trail markers, Vicksburg is a must-visit destination for anyone with a passion for the soulful sounds of the blues. Here, Visit Vicksburg breaks down the city's markers to infuse your next trip with a touch of musical history.

Night at: Oak Hall - King 


DAY 10

Continue to drive South direction the historic city of Natchez. Situated directly on the iconic Mississippi River, Natchez is one of the southeastern USA’s hidden gems. More than 1,000 structures in this Mississippi city are listed on the National Register of Historic Places, including homes dating to the late 1700s. They help preserve the city’s storied past, while cutting-edge cuisine and a lively social calendar offer year-round activities for modern travelers. And if you love music, travel the Gold Record Road, a driving tour of fascinating musical landmarks that’s part of the Americana Music Triangle.

Night at: Monmouth Historic Inn - Deluxe King 


DAY 11

Today, take the plantation road to New Orleans, your final destination. No matter the time of year, New Orleans welcomes its visitors in a grand way to experience Caribbean, Spanish, French and African cultures colliding in a brilliant explosion of flavors, emotions and sounds. Music is everywhere, people live to eat and every day is a party here in the birthplace of jazz, which is also home to Creole cuisine, centuries-old Spanish oak trees and clacking streetcars. With a unique combination of city life, swamp tours, festivals, historical significance and revelry during Mardi Gras, New Orleans has the recipe to captivate everyone.

Night at: One 11 Hotel - King 


DAY 12

After a well deserve morning at leisure, meet your musician guide who will open the doors of the French quarter Jazz Club for you. While walking along the French Quarter, your guide will tell stories of New Orleans' musical legacy for the first part of the tour. Then enjoy the best live jazz at select venues down on Frenchmen Street. Guided by an active musician that plays in the clubs regularly, you will get the best recommendations for the remaining of the evening and for the rest of your stay.

Night at: One 11 Hotel - King 


DAY 13

After a morning at leisure, drive back to the airport, drop-off your car rental and fly to your next destination. 

bottom of page