Exploring the Deep South

From soulful cities and historic landmarks to coastal charm and unforgettable food, my nine-day journey through Mississippi and Alabama was nothing short of extraordinary. Here’s how the adventure unfolded, day by day.

Day 1 – Flying In & First Impressions of Jackson

The trip began in style with a Premium Economy flight on Virgin Atlantic direct to Atlanta. The eight-hour journey was comfortable and surprisingly enjoyable, with an excellent choice of entertainment, three dinner options, afternoon tea, and a steady supply of drinks and snacks. The spacious seating made the flight feel far more relaxed than economy, and Virgin truly impressed with their premium service.

Arriving in Atlanta, I transferred to my connection for Jackson, Mississippi. A word of advice for anyone travelling to the U.S.: downloading the Mobile Passport Control app can save a lot of time at security, though do check it covers your destination first. I was also pleasantly surprised by how easy the luggage transfer was — within minutes our bags were re-checked and on their way to the next flight. With a three-hour layover (always wise for U.S. connections), I boarded a Delta flight and, just over an hour later, touched down in Jackson.

For my first night, I checked into the Old Capitol Inn, a boutique property only 15 minutes from the airport. With just 24 rooms, it’s a real hidden gem — elegant yet intimate, with a leafy garden and a touch of boujee charm. It was the perfect spot to recover from a long day of travel.

Day 2 – Jackson: The City With Soul

My first morning began with a tour of Downtown Jackson, a city that wears its nickname, “The City with Soul”, with pride. Stops included Brent’s Drugs in the Fondren District, the home of civil rights activist Medgar Evers, and the Mississippi Civil Rights Museum. The museum was an unexpected highlight of the day: eye-opening, powerful and deeply moving.

By the afternoon, I was on the road to Natchez, a two-hour drive that felt like slipping straight into the set of a Hallmark film. Natchez is a town full of Southern charm, with historic houses lining the streets and a warm, welcoming atmosphere. I first visited the Monmouth Historic Inn, where 30 rooms and suites are beautifully decorated with antiques. A cocktail in their grand bar felt like stepping back in time.

That night, I checked into the Dunleith Historic Inn, which quickly became my favourite stay of the trip. This grand estate offers 22 rooms across several buildings and even has its own Castle Pub for casual drinks and dinners. I was fortunate to be upgraded to the Honeymoon Suite — an indulgence that only added to the magic of staying here. Dinner in Natchez was at Frankie’s on Main, a relaxed spot where I sampled hearty Southern cuisine.

Day 3 – Historic Natchez & On to the Gulf Coast

The morning was devoted to history. At Longwood Mansion, I discovered the largest octagonal house in the United States, with its completed lower floor contrasting against the hauntingly unfinished upper levels. The family’s story and the building’s frozen-in-time beauty were fascinating. From there, I visited the Museum of African-American History and Culture, which preserves and shares the contributions of African Americans in the region.

Afterwards, we drove three hours south to Bay St. Louis, a lively coastal town perched on the Mississippi Sound. Its historic district is full of boutique shops, seafood restaurants and a strong sense of community. From there it was only a short hop to Biloxi, where I checked into the Hilton Garden Inn. This modern hotel, just steps from the beach, offered spacious rooms, a small pool overlooking the Gulf, and a hearty breakfast to start the day.

Dinner was at White Pillars Restaurant & Lounge, one of Biloxi’s finest. Housed in a beautifully restored mansion, the food was elegant and locally inspired. It was here I tried my first oyster — and loved it. To round off the evening, I wandered into the Hard Rock Casino for a little flutter, already planning what I might spend my winnings on.
 

Day 7 – Gulf Shores to Mobile

Breakfast was at Tacky Jacks, a colourful and quirky spot where even at breakfast it’s impossible not to try their signature Bushwacker cocktail. From there, we continued to The Hangout in Gulf Shores — a family-friendly beachfront venue offering live music, foam parties and a buzzing holiday atmosphere.

The day’s journey continued with a ferry ride across Mobile Bay to Dauphin Island before reaching downtown Mobile. Here I checked into The Admiral, a stylish historic hotel with a pool and a glamorous bar. In the evening, I joined a Mobile Pedal Tour — a lively way to see the city, pedalling between local pubs and breweries with music playing and plenty of laughter. Dinner at the Original Oyster House rounded off the day, with its waterfront setting the perfect place to watch the sunset.

Day 8 – From Mobile to Montgomery

The morning was devoted to history once again, beginning at the History Museum of Mobile before continuing to the Africatown Heritage House. This powerful museum tells the story of the Clotilda, the last known slave ship to arrive in the U.S., and of the community that its survivors built. It was a sobering but essential visit.

To balance the mood, I joined the Bienville Bites Food Tour, which combined sightseeing in Mobile with plenty of local dishes to try along the way. Later that afternoon, I drove on to Montgomery, where I visited the Rosa Parks Museum. Standing on the very spot where she refused to give up her seat in 1955 was an emotional experience that brought history vividly to life.

The evening was spent at my very first baseball game, cheering on the Montgomery Biscuits as they beat the Tennessee Lookouts 10-2. The atmosphere was electric, and of course I had to buy a team t-shirt as a souvenir.

Day 9 – Reflections in Montgomery

The final day began at the Freedom Monument Sculpture Park, a memorial along the Alabama River that honours the victims and legacy of slavery. It was a deeply moving place that encouraged quiet reflection.

Before heading to the airport, I made one final stop at Montgomery Whitewater, a brand-new adventure park with everything from rafting and kayaking to climbing walls and zip-lines. I didn’t have time to take part but even the tour was enough to see how much fun it would be for families or thrill-seekers.

Final Thoughts

Nine days across Mississippi and Alabama gave me everything I could have hoped for and more. From soulful Jackson and historic Natchez to the creative energy of Ocean Springs and the stunning beaches of Orange Beach, the Deep South is bursting with culture, charm and hospitality. Add in the moving museums, delicious food and the joy of live music, and this was a journey that will stay with me forever.

The Deep South may not always be the first destination people think of in the U.S., but after experiencing it for myself, I can wholeheartedly say it should be.