The Best Guide For Your Big Southern Driving Loop, Just Be Sure to Do This
- elleno1962
- Jan 14, 2024
- 6 min read

When my husband dragged me out of Texas in 1992 to return to Louisville, Kentucky where we would live the next four years, we stopped overnight in Mississippi. I had heard about the state’s Natchez Trace and vowed that someday, I would return to drive this important piece of American history.
That opportunity came in March 2022 after mass vaccinating for Covid 19 made it once again relatively safe to travel again. I knew just the trip to get back on the road.
The Big Southern Loop!
If a car trip to fascinating and lesser known parts of the southern US sounds intriguing, come along for the drive. I know very few folks who have ever visited the likes of St. Simons Island, Clear Lake City, Natchez, and Vicksburg but if you ever get the chance, make it happen!!
It’s the perfect retirement getaway.
If starting from the north, a great overnight pitstop is Suffolk, Virginia - (magnet #58). Home of Planter’s Peanuts, Suffolk earns the title of “Peanut Capital of the World”. It's rail museum is temporarily closed unfortunately.
Over the next several days, we visited several coastal communities such as Topsail Beach, NC, St. Simons Island, Georgia (magnet # 59), and Sea and Jekyll Island, Georgia. You can easily make an entire vacation focused on these four idyllic spots alone.

After a great visit to see my brother Beau and wife Sylvia on Topsail Island, NC, we took Highway 17 S to St. Simon's Island, Georgia. My brother Beau recommended the Village Inn and Pub and for good reason. Everything about this small inn evokes southern comfort and hospitality. We walked to the nearby Blue Bay Mexican restaurant where I “enjoyed the best fish tacos ever” according to my travel notes. On our second night, we had a fabulous dinner at Georgia Sea Grill while enjoying live piano music.

Though my parents honeymooned at Sea Island, staying at the resort wasn’t in this trip’s budget. Instead we spent two nights at the Sea Island Inn. I’m not sure we could have asked for better accommodations. This lovely hotel offers a heated pool warm enough to actually swim in in February, bicycles, and a happy hour where you are certain to meet a few interesting characters.

One highlight was visiting Fort Frederica National Monument (magnet # 60) Take the guided tour; we found the ruins quite fascinating. Frederica was built by James Oglethorpe in the mid 1700’s to protect this southernmost part of his newly formed colony called Georgia from Spanish invaders. Who knew?

After stopping in at the Jekyll Island Club Resort and the nearby Georgia Sea Turtle Center, it was time to head west. With no reservations, Pete and I started driving toward Houston, 14 hours away.

500 miles later, we found ourselves in Biloxi, Mississippi. First of all, Biloxi has beautiful beaches! I had no idea. We excitedly called the Hampton Inn in Biloxi only to find out the hotel was completely sold out -and it was February! Disappointed, we pushed on to the neighboring town of Gulfport (heavily damaged by Hurricane Katrina in 2005). Gulfport seems to still be making a comeback but our Hampton Inn was quite lovely. But folks, if you are ever in Biloxi, stay at the Hampton Inn overlooking the gulf. The hotel views must be phenomenal.

Well rested, we made the drive from Gulfport to Clear Lake City, Texas in under seven hours. For this stay of 10 days, I found a delightful Airbnb just a mile from where we lived from 1989-1992,

Traveler’s Tip: For longer stays, Airbnb is a great way to economize. We enjoyed a pool, hot tub, and enough space to entertain family and friends while saving a bundle.


If you are ever in the Houston area, take my advice and visit the NASA’s Johnson Space Center (magnet # 61 ). No matter what your age or interest level, I guarantee you will be blown away by the exhibits and interactive displays. Nothing in Disney World compares to the real feel of space exploration during your indoor and outdoor tours.
Having reached our most southern destination of “the loop”, we headed north on March 6, 2022. An easy five hour drive away, we pulled into Natchez, Mississippi mid afternoon. Determined to live a bit like Scarlett O’Hara, I found online the lovely 1898 Devereaux Shields House. Booking early, I snagged the apparent ‘best room'' in the inn called The Gallery Suite. Guests who were checking in behind us sniffed, “That’s the room we wanted”.

No, I didn’t trade.
Travelers Tip: It’s always worth the homework when booking at inns where the rooms can differ so much. Book as early as you can to avoid being disappointed.
Natchez, founded in 1716, is the oldest settlement along the mighty Mississippi. If you are interested in antebellum homes, Natchez is rich with beautifully restored mansions such as Rosalie, Longwood, and Stanton Hall. Rosalie stands out as having the most beautiful authentic interior furnishings of any historical US home I’ve ever toured.

During our stay, we drove about 30 miles of the Natchez Trace, stopping to walk a short distance of the Sunken Trace at milepost 41.5. Here you can walk the exact same path American Indians and early settlers of the 1700’s once navigated by foot. It’s truly awe inspiring and worth the stop.


But it was the haunting Windsor Ruins which most captivated my imagination decades ago when reading an article in Southern Living. The mansion’s owner, Smith Daniell only lived a few weeks after the mansion was completed in 1861. All that’s left of the largest antebellum home ever built in Mississippi after a disastrous fire in 1890 are 23 corinthian columns and a bit of ironwork. You can’t help but feel the eerie pall that penetrates your soul when walking the grounds.
After our delightful stay in Natchez, we moved on to Vicksburg, most noted for its National Military Park. This time, we truly dug into confederate history and stayed at the Anchuca Mansion. It was on this historic mansions’ front balcony where Jefferson Davis made his last public address.


To experience more history, we moved over to the Duff Green Mansion our second night in town. Both Jefferson Davis and Ulysses S. Grant were previous guests. During the Civil War, Duff and Mary Lake Green, the owners, hedged their bets (most certainly saving their home) by making their residence a military hospital for both sides. Blue troops recuperated on the upper floor, confederate gray on the second. Our guest room in the basement, the Dixie, served as the operating room. Legend has it that the room is haunted by a “legless” soldier. Alas, he did not make his presence known to us during our stay.

It was at the Duff Green where we dined in the formal dining room for breakfast being waited on by friendly staff who truly extended southern hospitality.

Travelers Tip: The Vicksburg Military Park is incredibly beautiful, worthy of at least a full day of exploring. The remnants of the Northern gunboat, the Cairo (magnet # 62 ), is on display under its own tent. All Union gunboats were named for towns along US rivers i.e. the Cincinnati, the Louisville, and

From Mississippi, we traveled to Nashville and Kentucky to visit family. On March 18th, we arrived back in Philadelphia.
It was a fantastic trip and we had only one regret.
Traveler’s Tip: We were cold during much of our travels, including Houston, Texas. I recommend driving your own “Big Loop” a few weeks later, starting in late March or in October, when things start to cool down “down South”.
But whenever you go, take your time, enjoy the slower pace you’ll find in the lower states. One last piece of advice.
Traveler’s Tip: Our waitress in Vicksburg said Pete and I stuck out like sore thumbs. I asked her “How’s that?”
She responded, “Well, for one thing, you didn’t say “Hey ya’ll” when you walked in and worse, “You didn’t order southern food”. She suggested, “Next time, order the shrimp n’ grits.”
Grits — synonymous with the south. Most every breakfast featured a variation of eggs, grits, bacon and biscuits. Nothing wrong with any of these delicious items but trust me, if you’re going to dine on biscuits, gravy, grits, and bacon for a month, be sure to pack some loose clothing for the ride home.
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