If you love live music, great food, and cities that don’t believe in early nights, this Deep South Road Trip Itinerary is for you. In just a few stops, this itinerary will take you through destinations that shaped entire genres of music, each with its own soundtrack from jazz to blues to rock ‘n’ roll and country.
Built around legendary music cities, this road trip runs from The Big Easy (New Orleans) to Elvis’ Memphis and on to Music City (Nashville, Tennessee). While it works to take this deep south road trip itinerary in either direction, we chose to start in New Orleans and finish in Nashville, saving the late nights and lively bar scene for the end.
For those just starting their Deep South Road Trip itinerary research, the Deep South refers to a specific region deep in the southeastern part of the United States. Traditionally, the Deep South includes: Louisiana, Mississippi, Alabama, Georgia, and South Carolina. Sometimes parts of Tennessee and Florida are included as well.
Okay, let’s get into planning your Deep South Road Trip Itinerary…
Getting to/from New Orleans and Nashville
Most travellers entering the U.S. will need an Electronic System for Travel Authorisation (ESTA), which can be applied for online and is usually processed within 72 hours. Make sure you do this well in advance of your flight departure.
British Airways flies direct between London Heathrow and both New Orleans and Nashville. If you’re looking to save money on your Deep South Road Trip Itinerary, it is usually cheaper to connect via cities like New York, Chicago, Orlando, Miami or Dallas. We spent a few nights in New York because it was the cheapest direct flight from the UK to the U.S., and then flew to New Orleans with United Airlines for under £100.
Renting a car for your Deep South road trip
We rented a car with Avis via Booking.com, picking it up in New Orleans and returning it in Nashville. Although we had no issues on this trip, we have since found it better to book insurance directly with the rental company, as Booking.com’s provider reimburses you after you pay any costs upfront.
At first, I was intimidated by our seven-seater Kia Telluride, but I’m glad we chose a large car. Most vehicles on the road are big, and I felt much safer driving in it than in a smaller car.
When to visit the Deep South
We visited in July, and the heat and humidity were intense. We struggled walking anywhere for too long, especially in Memphis and Nashville, and had rain showers in New Orleans.
For more comfortable temperatures, I’d recommend travelling during the shoulder seasons of April to May or September to October. Keep in mind events like Mardi Gras in New Orleans (the Tuesday before Ash Wednesday) or CMA Fest and Bonnaroo in Nashville (usually in June) can make the cities much busier.
Day 1 Deep South Road Trip Itinerary
Rise and shine, it’s your first day in NOLA! Start your trip at Café Du Monde, New Orleans’ iconic coffee stand famous for its chicory coffee and powdered-sugar-covered beignets.
Top tip: Carry cash! Cafe Du Monde is strictly cash-only, and since it’s open 24/7, you’ll want to be ready whenever a beignet craving strikes. Cash is also handy for jazz bars, where it’s customary to tip the musicians (typically $10 to $20 per person).
Once you’re fueled up, it’s time to begin exploring the historic heart of New Orleans. Make sure to visit:
- French Market
- Jackson Square
- St Louis Cathedral
- Royal Street
- Old Ursuline Convent
Be sure to stop for a drink at the Vampire Cafe and try their novelty Blood Bag Cocktail.
For dinner, we headed to Coop’s Place, a Decatur Street favourite and the perfect pit stop before exploring the jazz bars at Frenchman Street. This local staple serves up classic New Orleans cuisine with a side of attitude – think Karen’s Diner, but with a Creole twist and strictly over 21.
We then headed to The Spotted Cat Music Club, open seven days a week, 2pm to 2am, with local musicians playing their hearts out.
Day 2 Deep South Road Trip Itinerary
No Deep South Road Trip Itinerary is complete without a swamp tour. We booked through Cajun Encounters Swamp Tour and can highly recommend it. Our 12:15 PM tour included a 10:15 AM pickup from one of six locations. The hour-long coach ride flew by thanks to our entertaining guide.
Upon arrival, we boarded small, flat-bottomed boats captained by locals, spotting alligators, raccoons, spiders, grasshoppers and crawfish while learning about swamp life and the impact of Hurricane Katrina.
Top tip: Bring cash to tip both your tour guide and driver.
We returned to the French Quarter around 3pm and headed to Napoleon House, a historic restaurant once intended for Napoleon Bonaparte. We skipped the famous Muffuletta for Creole Jambalaya, which did not disappoint.
Being in one of America’s most haunted cities, a ghost tour is a must, delving into the dark histories of LaLaurie Mansion, Jackson Square, and the Bourbon Orleans Hotel. Once your spooks are satisfied, unwind at The Carousel Bar in Hotel Monteleone, a rotating 25-seat bar once frequented by Hemingway and Tennessee Williams. Top tip: It’s first-come, first-served with live entertainment from Wednesday to Sunday.
For a livelier night, head to Bourbon Street for bars, clubs, and live music. Look out for revellers tossing beads from the balconies above, and be sure to try the famous “hand grenade” cocktail, and visit the historic (and reportedly haunted) Latiffe’s Blacksmith Shop for their signature Voodoo daiquiri, aka Purple Drank.
Day 3 Deep South Road Trip Itinerary
Today, it’s time to explore another side of the city with a ride on the St. Charles streetcar to the Garden District. This charming 19th-century neighbourhood is known for its oak-lined streets and stunning antebellum mansions. Highlights include homes once owned by celebrities such as Sandra Bullock and Nicolas Cage, the iconic Buckner Mansion, featured in American Horror Story: Coven, and Lafayette Cemetery No. 1, one of the oldest city-governed cemeteries. Be sure to stroll down Magazine Street, browsing boutique shops and cafes, or visit the iconic Commander’s Palace for renowned Creole cuisine.
Spend your evening aboard the Steamboat Natchez Jazz Cruise. Enjoy a two-hour cruise along the Mississippi River that blends live traditional jazz music with fascinating historical insights about the river and the city. For the best experience, try to time your cruise with sunset for stunning views along the water.
Day 4 Deep South Road Trip Itinerary
The Deep South Road Trip Itinerary officially begins!
After picking up the rental car, we set off for our first stop: Parkway Bakery & Tavern. Countless recommendations and deep-dive research all pointed to this spot as home to one of the best po’ boys in New Orleans, and it didn’t disappoint. Just a 10-minute drive from Bourbon Street, Parkway has been serving up the iconic po’ boys since the 1920s, and they’ve truly perfected the craft.
What is a po’ boy?
A sandwich originally from Louisiana. It traditionally consists of a filling, which is usually roast beef, ham, or fried seafood on a New Orleans French bread roll.
With food sorted, it’s time to hit the legendary Blues Highway and begin the six-hour drive to Memphis, Tennessee. We chose to tackle the journey in one go. For those who prefer to break up the drive, however, there are plenty of worthwhile stops along the way.
- Baton Rouge, Louisiana: historic plantations and Louisiana history
- Natchez, Mississippi: Natchez Trace Parkway and historic homes
- Jackson, Mississippi: Civil Rights history and museums
- Vicksburg, Mississippi: Civil War battlefield history
- Tupelo, Mississippi: Elvis Presley’s birthplace (306 Elvis Presley Drive, where he lived until the age of 13)
After a long day on the road, we arrived in Memphis after dark and opted for an early night, ready to make the most of our one full day in the city.
Day 5 Deep South Road Trip Itinerary
Start your Deep South Road Trip Itinerary, day 5 at Graceland, Elvis Presley’s famous Memphis home!
I wasn’t quite sure what to expect, but I certainly did not anticipate it being located right off a major highway, with the Graceland Mansion on one side and the archives and Elvis’ jets on the other, connected by a steady stream of mini-buses ferrying visitors back and forth.
We booked the Elvis Experience online, which included a self-guided tour of the mansion, the EPM Entertainment Complex, and Elvis’ custom jets. We spent around three hours exploring, though my parents spent most of the day when they visited a few years ago.
Top tip: If you plan to visit around Elvis’ birthday (January 8) or Elvis Week (around August 16), be sure to book tickets well in advance, as these are very popular times to visit.
For lunch, stop at Gus’ World Famous Fried Chicken, then stroll down Beale Street, known as the “Home of the Blues”, and enjoy a drink at Rum Boogie Cafe, with its wall of autographed guitars.
A must-see activity is watching the famous Peabody Hotel March of the Ducks. Every day at 11am and 5pm, the ducks parade along a red carpet from the roof to the lobby fountain and back, guided by the “Duckmaster”. Top tip: Arrive 15-30 minutes early for a good view.
Dinner at Charlie Vergos’ Rendezvous restaurant, a basement BBQ spot, is a Memphis classic. After loading up on ribs, nachos, and beef brisket, we made our way back along Beale Street, hopping between bars and soaking up the live music at its iconic venues.
Top tip: If time allows, visit Sun Studio, “The Birthplace of Rock ‘n’ Roll”, where legends like B.B. King, Elvis Presley and Johnny Cash recorded.
Day 6 Deep South Road Trip Itinerary
To keep costs down, we rented our car for just 48 hours, which meant returning it to Nashville by 11 am. This required an early start, leaving Memphis at 7 am to begin the three-hour drive to Nashville.
Once we arrived and dropped our bags at our Airbnb, we headed to the Assembly Food Hall for a quick lunch before making our way to take in the wild and wonderful sights of Broadway.
After confirming that, yes, we could totally fit in with our cowboy boots and hats, we checked in and got ready to spend the rest of the day and night hopping between multi-story honky tonks and rooftop bars, chasing down as much live country music as we could find.
Day 7 Deep South Road Trip Itinerary
Start the day by shaking off last night’s festivities with brunch at Biscuit Love in the Gulch. Afterwards, take some time to wander around this trendy neighbourhood, browsing chic boutiques and snapping photos of its many Instagram-worthy murals.
Tonight, experience one of Nashville’s most iconic traditions at the Grand Ole Opry. Home to country music legends, rising stars, and the world’s longest-running radio show since 1925, the Opry delivers an unforgettable live performance. Shows typically run for about two hours and include a 15-minute intermission.
Day 8 Deep South Road Trip Itinerary
Kick off day eight with a coffee at Frothy Monkey before heading to the Country Music Hall of Fame, often referred to as the “Smithsonian of country music”. Spend the morning exploring the genre’s evolution, from legends like Jimmie Rodgers and Dolly Parton to modern stars such as Taylor Swift and Lainey Wilson.
Afterwards, make your way to East Nashville. Known for its mural-covered buildings, quirky shops, and creative spirit, this vibrant neighbourhood is the perfect place to wander in the afternoon.
When hunger strikes, stop by The Pharmacy Burger Parlour & Beer Garden, where the burgers have been described as medicine for the soul.
For a more intimate live music experience than Broadway’s busting honky-tonks, head to The Bluebird Cafe. This legendary 90-seat venue is known for discovering and hosting stars such as Taylor Swift, Keith Urban and LeAnn Rimes – reservations are highly recommended, as shows regularly sell out.
Day 9 Deep South Road Trip Itinerary
We decided to spend the last full day of our Deep South Road Trip Itinerary in Nashville soaking up the sun and relaxing by a pool.
We purchased a day pass for Conrad Nashville via ResortPass for $30 per person, which provided access to the outdoor pool and lounge chairs (first-come, first-served) as well as towels, with food and drinks available for purchase. It was the perfect, relaxing end to a busy trip.
If you’re not ready to rest your legs up just yet, I’d suggest a day trip to a nearby town like Franklin (20 miles/25-minute drive) or Leiper’s Fork (30 miles/40-minute drive).
Day 10 Deep South Road Trip Itinerary
It’s home time! Before saying goodbye to Nashville, head back to your favourite brunch spot for one last bite or swing by Assembly Hall to revisit a favourite food stall. After soaking up the last of the city’s flavours and atmosphere, make your way to the airport, either with a quick 15-minute taxi ride or by hopping on the WeGo Public Transit Route 18 bus.
Have you been to the Deep South?
Thank you so much for reading! I hope it’s given you all the inspiration to plan and book your own epic Deep South Road Trip.
You can follow Kirstie’s adventures on TikTok here.
