Southern Charm
There’s a reason “y’all” sounds like a hug. Last May we spent 9 days working our way up the Southeastern coast — one night in Orlando, three in Savannah, three in Charleston, a night in St. Augustine and a final night in Orlando near the airport. We also took side trips into the Lowcountry areas of Bluffton, Hilton Head and Kiawah Island along the way. By the end of our stay we understood exactly why people fall in love with this stretch of America. Spanish moss, antebellum porches, fresh shrimp, and a level of hospitality that makes you want to slow your whole life down. Here’s how it went.
Spanish moss hanging from the live oaks set the tone for the entire trip .
Orlando — A Quick Landing Pad
We flew into Orlando because it was a direct flight and we were able to use our Alaska Companion fare. One night in Orlando was never going to be enough to do the parks justice, and that wasn’t really the point of this trip. We did fit in a visit to Epcot and enjoyed wandering through the World Showcase and eating and drinking from the offerings of the varios countries represented. We had a wonderful dinner with some old friends and then in the morning we jumped on I-95 and headed to Savannah.
We will have to make a return trip to see more of what Disney and Orlando have to offer.
Savannah — Three Nights of Spanish Moss and Southern Gothic
Savannah is the kind of city that makes you walk slower without realizing you’re doing it. Founded in 1733, it’s one of the oldest planned cities in the country, laid out around a series of shaded public squares. Three nights here felt about right — enough time to actually settle into the rhythm of the place instead of just checking boxes.
Forsyth Park anchors the southern end of the historic district, and its fountain, installed in 1858, is the photo everyone takes — and rightly so. We’re also calling out Jones Street specifically because locals weren’t exaggerating when they told us it’s the prettiest street in Savannah. Cobblestones, towering oaks, and rows of restored townhouses make it a slower, quieter cousin to the more famous squares nearby.
Beautiful Forsyth Park
The fountain at Forsyth Park is the unofficial symbol of Savannah, and it’s even better in person than in every postcard you’ve seen.
Walking around the Savannah Historic District we stopped by Chippewa Square, famous as the spot where Forrest Gump sat on his bench (the bench itself is long gone, now in a museum). The whole area is shaded by enormous live oaks dripping with Spanish moss, and every few blocks reveals another perfectly restored 18th or 19th century home.
The Gingerbread House, also known as the Cord Asendorf House, is a historic landmark built in 1899.
The Cathedral Basilica of St. John the Baptist, with its twin Gothic spires and genuinely stunning interior ceiling work
Another stop worth your time in the historic district is the River Street area where Savannah gets its waterfront energy, all cobblestones, old cotton warehouses turned into shops , candy stores, restaurants and bars.
Boar’s Head Grill & Tavern is the oldest continuously operating restaurant on Savannah’s Waterfront, offering spectacular views of the Savannah River.
The Georgia Queen paddling on the Savannah River past the old cotton warehouses on River Street.
But the place that really stayed with us was Bonaventure Cemetery. If you’ve read Midnight in the Garden of Good and Evil, you already know its reputation, but even without the book it’s worth the short drive out of downtown. Moss-draped oaks arch over Victorian-era statuary and family plots overlooking a bend in the river — it’s hauntingly beautiful rather than morbid, and we spent far longer wandering there than we expected to.
Bonaventure Cemetery — equal parts eerie and gorgeous, and one of the most photographed cemeteries in the country for good reason.
In addition to the Spanish moss everywhere we loved all the Southern Magnolia, with their huge waxy white blooms, – they show up everywhere from front yards to public parks.
Out at Wormsloe Historic Site, just south of downtown, you get the moss-draped-oak experience without a single tourist trinket shop in sight — a mile and a half avenue of live oaks leads to the ruins of a colonial estate built by one of Georgia’s original settlers in the 1730s. It’s one of the most photographed driveways in America, and walking it yourself, it’s obvious why.
The oak avenue at Wormsloe — a mile and a half of pure Southern Gothic before you even reach the ruins.
The Lowcountry Detour — Hilton Head, The Angel Oak, and Kiawah Island
Between Savannah and Charleston, we slowed things down even further with a swing through the Lowcountry. A short hop away, Hilton Head Island delivered exactly what it promises: world-class golf courses threading through maritime forest and dunes. The Harbour Town resort area with the candy-cane-striped Hilton Head Lighthouse was beautiful. You can actually climb the lighthouse for a sweeping view over Harbour Town and the marina below.
The Hilton Head Lighthouse’s red-and-white stripes make it one of the most recognizable landmarks on the island.
We also carved out time for Kiawah Island— this is home of the Ocean Course, host to multiple PGA Championships and some of the widest, least crowded beaches we found on the entire trip. If you golf, build in extra time here; if you don’t, the beaches alone are worth the detour.
The golf courses at Kiawah were pristine and made me wish that I had the time and my clubs with me.
The Angel Oak Tree on Johns Island — a Southern live oak estimated at 400-500 years old, with a canopy that shades an area of over 17,000 square feet. Photos genuinely don’t do it justice; standing under those low, sprawling limbs feels like standing inside something ancient rather than just looking at a tree.
The Angel Oak — centuries old, and one of those rare sights that’s actually more impressive in person than in any photo.
Charleston — Three Nights of Antebellum Elegance
Lovely Charleston is polished and proud of it — and three nights here gave us just enough time to fall for the city properly.
Rainbow Row’s pastel houses are about as Instagram-famous as Charleston gets, and they’re even better in early morning light before the crowds arrive
Rainbow Row is the postcard shot everyone comes for — a stretch of pastel-colored historic houses along East Bay Street, the longest cluster of intact Georgian row houses in the U.S. — but the real charm of Charleston is in just wandering the streets in the area they call South of Broad and taking in the antebellum homes with their wraparound piazzas and walled gardens.
One of the many stunning antebellum homes gracing the streets of Charleston
Out in Charleston Harbor lies Fort Sumter, the site where the first shots of the Civil War were fired in 1861. The boat ride alone is worth it for the skyline views, and the fort itself, now a National Monument, does a genuinely good job of laying out the history without feeling like a lecture.
Fort Sumter sits right in the middle of Charleston Harbor — accessible only by boat, which makes the visit feel like more of an event.
Charleston is a great city to wander around, beautiful parks, historic homes, manicured gardens and lots of fountains. Joe Riley Waterfront Park is a nice place to cool off, with its famous Pineapple Fountain (pineapples being the South’s unofficial symbol of hospitality).
The Pineapple Fountain at Joe Riley Waterfront Park — pineapples are everywhere in Charleston, and now we understand why.
The US Custom House is a marble Greek Revival building that took over a decade to finish — partly because construction was paused during the Civil War.
We also made it out to Folly Beach Fishing Pier, a solid stretch of beach a short drive from downtown with a long pier extending out into the Atlantic — a good antidote if you need a break from historic homes and house museums.
Folly Beach Pier — Charleston’s answer to a proper beach day.
And for something quieter and more reflective we visited Magnolia Cemetery, a Victorian-era garden cemetery on the Cooper River. Similar in look and feel to Bonaventure Cemetery in Savannah — Spanish moss, monuments, and a surprising number of Confederate generals and Civil War submarine crew buried among the live oaks.
Looking at the civil war headstones I noticed a large section of gravesites all with the same dates between July 1st and 3rd of 1863. Then it dawned on me – Gettysburg.
St. Augustine — One Night, A Lot of History
Our last stop was a single night in St. Augustine, Florida — the oldest continuously occupied European-founded city in the continental United States, established by the Spanish in 1565. One night isn’t enough, but it’s enough to hit the highlights. The Castillo de San Marcos National Monument is the must-see: a 17th-century Spanish fortress built from coquina, a sedimentary stone made of compressed shells that, somewhat famously, was excellent at absorbing cannonball impacts without shattering. It’s the oldest masonry fort in the continental U.S. and still looks ready for a siege.
Castillo de San Marcos has guarded St. Augustine’s harbor since the 1670s and is still standing.
From there we walked St. George Street, the pedestrian-only heart of the old town, lined with colonial-era buildings now packed with shops and restaurants. You’ll also see the oldest wooden school house in the USA (see above). We crossed the Bridge of Lions, the ornate drawbridge guarded by a pair of marble lions that connects downtown to Anastasia Island.
The Bridge of Lions, with its marble lion statue standing guard
We made time for the Cathedral Basilica of St. Augustine, the oldest Catholic parish in the continental U.S. (the current building dates to the 1790s), and paid our respects at the bronze statue of Juan Ponce de León, the Spanish explorer credited with naming Florida and searching, unsuccessfully, for the Fountain of Youth nearby.
The bronze statue of Juan Ponce de León — Florida’s reluctant namesake, still looking for that fountain.
We finished at the St. Augustine Lighthouse, its black-and-white spiral stripes visible from much of the old town, sadly my knees couldn’t make the climb up the 219 steps for a sunset view.
The St. Augustine Lighthouse’s spiral stripes make it one of the most photographed lighthouses in Florida
The Verdict
This was a trip of contrasts — Savannah’s gothic, moss-draped melancholy, the unhurried Lowcountry charm of Bluffton and the islands, Charleston’s polished antebellum pride, and St. Augustine’s history as the oldest city in the USA. If we had to do it again, we’d give Charleston a fourth night and add another night in St. Augustine, but otherwise this route is about as good a sampler of the Southeastern coast as you’ll find. Spanish moss, sweet tea, crab cakes, fried chicken and hush puppies and a whole lot of Southern charm — two thumbs up from us.