The Deep South: Chicago to New Orleans road trip

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    You'll hear plenty of soulful jazz in New Orleans
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    Be transported back in time as you arrive in Clarksdale

    Be transported back in time as you arrive in Clarksdale

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    Drive through the gorgeous Kentucky countryside | Travel Nation

    Drive through the gorgeous Kentucky countryside

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    Hop between live music bars in Nashville | Travel Nation

    Discover Nashville, the heart of country music

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    Discover the southern charm of Natchez, nestled on the Mississippi river

    Discover the southern charm of Natchez - nestled on the Mississippi river

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    Memphis is the home of rock’n’roll, blues and jazz

    Memphis is the home of rock’n’roll, blues and jazz

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    Start with a trip to the Cloud Gate, more popularly known as “The Bean”

    Wander the bustling streets of Chicago

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    Head to the French Quarter for a truly unique experience

    Head to the French Quarter for a truly unique experience

Tailor-made holidays

Duration(in days): 16

From: UK




Inc. International flights (Per person, based on 2 sharing)

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    Drive yourself from Blues to Jazz on this 2 week southern states road trip. Crossing 6 states, you’ll drive from Chicago to Memphis via Nashville and Louisville, then Memphis to New Orleans along the ‘Blues Highway with opportunities to visit the Mississippi River, the Country Music Hall of Fame, Graceland and to stay in an authentic cotton plantation.  You’ll discover how America’s history is deeply-rooted in its music from the blues & bluegrass of Chicago and Kentucky to the birthplace of rock’n’roll in Memphis, finishing with some jazz and a beignet in New Orleans.This itinerary can be tailored to suit your requirements please contact one of our consultants to start planning your dream American road trip.

    This holiday includes

    • International flights
    • Accommodation as mentioned in the itinerary 
    • Meals as mentioned in the itinerary 
    • Excursions as mentioned in the itinerary        
    • Car hire car hire  

    You'll remember... 

    • Tucking into a deep-dish pizza and listen to the blues in Chicago      
    • Tasting some local bourbon in Kentucky 
    • Dancing in the honkytonk bars of Nashville
    • Visiting Elvis Presley’s home, Graceland and Sun Studios
    • Driving the ‘Blues Highway’ from Memphis to Clarksdale
    • Staying on an authentic cotton plantation
    • Getting the full American experience at a traditional Delta Blues Club                            
    • Discovering the French Quarter in New Orleans     


    Itinerary in brief:

    • 2 nights Chicago
    • 2 nights Louisville
    • 2 nights Nashville
    • 2 nights Memphis
    • 1 night Clarksdale
    • 2 nights Natchez
    • 3 nights New Orleans


    Day 1: Depart UK

    On arrival in the Windy City, you will make your own way to your hotel, where you will check in for two nights.

    Included:  International flight, hotel

    Day 2: Chicago

    Start with a trip to the Cloud Gate, more popularly known as “The Bean” where you can snap a photo in its distorted reflection, before heading to Intelligentsia Coffee for a latte. Don’t miss two of America’s best museums - The Art Institute of Chicago holds paintings by Picasso and O’Keefe, as well as the famous American gothic portrait by Grant Wood, while at the Field Museum you can visit Sue, the most complete T-Rex skeleton ever found. Enjoy a slice of Chicago deep dish pizza at Giordano’s before a night of comedy at Second City, where famous comedians like Tina Fey and Steve Carrell made their debuts. Don’t leave before heading to the top of the Willis Tower SkyDeck, where you can stand in a glass box high above the city and admire endless views of the city and Lake Michigan below.

    Included: 4* Hotel

    Day 3: Chicago to Louisville

    After picking up your rental car, you’ll leave Chicago behind and take the road to Louisville. This drive takes a few hours so a great place to stop for lunch is Indianapolis, where you could try Indiana’s favourite pork tenderloin sandwich. On arrival in Louisville you will check into your hotel for two nights.

    Included: Hire car, 4* hotel 

    Day 4: Louisville

    Today is yours to explore the city at your leisure. We recommend visiting the Kentucky Derby Museum, where you can learn about the extraordinary experience of this world-famous horserace as well as meeting their resident thoroughbred and the miniature horse called Winston. After that, you can head to Churchill Downs, where the race takes place, before driving to Frankfort Avenue, the road that connects the city’s most charming historic neighbourhoods. It’s the perfect place to grab a ‘hot brown’ for lunch – a Louisville classic open sandwich made of turkey, mornay sauce and cheese - in a cute café. You can spend the afternoon in ‘Museum Row’, hopping between science, history and sports museums, before hitting a bar with some live bluegrass and grabbing a glass of bourbon.

    Included: Hire car, 4* hotel 

    Day 5: Drive to Nashville

    This morning you can start your journey south to Nashville, driving through the great state of Kentucky. We recommend a stop in Bardstown, a pretty little town in the heart of bourbon country. Visit the Oscar Getz Museum of Whiskey where you can learn about the prohibition years and how they affected this part of the US before stopping in at one of the area’s many distilleries, like the Willett Distillery to learn how this delicious and uniquely American spirit is made. It’s a beautiful part of the country to drive through with rolling green hills while you drive past pretty farms. Pass into Tenessee and continue to Nashville, where you’ll check into your hotel for two nights.

    Included: Hire car, 4* hotel 

    Day 6: Nashville

    Start your time in the music city with a visit to the Country Music Hall of Fame & Museum which has ever changing exhibits displaying the best the genre has to offer before wandering along Music Row to visit the historic RCA Studio B where Elvis recorded many of his tracks. Stop for a plate of hot chicken, Nashville’s favourite meal and take a walk-through Centennial Park, where you’ll find a full-scale reproduction of the Parthenon. There is so much more to see and do here – the Johnny Cash Museum, learning to line dance in one of the dance halls, devouring a plate of meat and three – your days here will be busy! Spend each evening on Honky Tonk Highway – this street of country music bars is where many legends like Willie Nelson and Gretchen Wilson started their careers and will be chock full of budding musicians to keep you entertained.

    Included: 4* hotel, hire car, Country Music Hall of Fame & RCA Studio B Entry

    Day 7: Drive to Memphis

    Why not spend your morning in Nashville - you could head over to 12South, one of the coolest neighbourhoods in the city. There are lots of beautiful shops - including Draper James which is owned by Nashville’s sweetheart Reese Witherspoon – you can take a photo at the iconic “I Believe in Nashville” mural before tucking into a brisket sandwich at Edley’s Bar-B-Que for lunch. In the afternoon you’ll drive 3 hours west to Memphis, where you’ll check into your hotel for two nights.

    Included: 4* hotel, hire car

    Day 8: Memphis

    Home of rock’n’roll, blues and soul, Memphis is renowned for its music. Pay homage to Elvis Presley by visiting his former mansion, Graceland and make sure you stop in at Sun Studios – the iconic recording studio used by The King himself, Johnny Cash and B.B King. Beale Street is the place to go to hear live music, so head down and find yourself some blues music to tap your foot to, whilst digging into some tasty Tennessee barbeque!

    Included: 4* hotel, hire car

    Day 9: Drive to Clarksdale  

    Deep in the Mississippi Delta, you will find The Shack Up Inn, Clarksdale. Prepare to be transported back in time to an authentic cotton plantation, gifted with unique accommodation, and treated to a bona fide blues club. Spend the afternoon on the porch, sipping a cold beer and soaking up the atmosphere in this completely original setting. 

    Included: 3* hotel, hire car  

    Day 10: Drive to Natchez

    Your drive today takes you south to the city of Natchez, nestled on the banks of the Mississippi and bursting with Southern Charm. You will check in for your 2 night stay.

    Included: 3* hotel, hire car

    Day 11: Natchez

    Natchez is full of heritage architecture and untouched historic homes and is a charming town to discover. Here you will get a genuine and casual welcome, with delicious southern cuisine and hospitality to match. Along with the historic landmarks, there are also many parks and trails to take advantage of.     

    Included: 3* hotel, hire car

    Day 12: Drive to New Orleans      

    It’s time to leave Mississippi and head into Louisiana, and New Orleans. Locally known as “Nola”, and internationally known as one of the most diverse and cultural cities in America, you will have the chance to get under the skin of this fascinating destination with your 3 night stay. On arrival in New Orleans this afternoon you’ll drop off your hire car at the depot – you won’t need it in walking friendly New Orleans.

    Included: 4* Hotel, hire car  

    Day 13 & 14: New Orleans

    Spend a couple of days exploring the eccentric city of New Orleans. We’d recommend you start with a stop at Café du Monde, where you’ll have to queue to get your hands on a bag of the famous beignets which will give you the energy you need to explore the city. Wander through the French Quarter past pretty balconies and colonial architecture and into one of the ornate cemeteries – “Cities of the Dead”, where huge carved angels look down on you from their plinths. New Orleans certainly has a spooky side to it – make sure you explore the voodoo history of the city and look out for ghosts that supposedly lurk around every corner. Finish up by enjoying a bowl of gumbo or a plate of ruby red crawfish served with buttery sweetcorn and andouille sausage for dinner. On your first day we’ve included a food tour of the French Quarter, to make sure you don’t miss out on New Orlean’s delicious highlights.

    Included: 4* Hotel, Food tour

    Day 15: Depart New Orleans

    Have one final stroll downtown before making your own way to the airport for your flight home.

    Included: International flight

    Day 16: Arrive UK

    During the summer months (July and August) New Orleans can get extremely hot, and busy. A good time to travel is April – June, or September – October, as the temperature will be more comfortable.

    Due to the unique property we use in Clarksdale, this itinerary may need to be altered and amended due to availability.

    This itinerary is purely a suggestion, and can be tailor-made to your requirements, so please contact us with your dates and requests and we’ll put together a bespoke quotation for you.

    What's included
    • International flights
    • Private arrival transfers in Chicago
    • Private departure airport in New Orleans
    • 9 days’ car hire
    • 14 nights’ accommodation
    Not included
    • Any meals not mentioned
    • Personal expenses
    • Tips and gratuities
    • Fuel

    14 nights in 3/4* standard accommodation. Hotels in this standard include:

    • Hotel Lincoln, Chicago

    • Shack Up Inn, Clarksdale

    • Bienville House, New Orleans