Curator’s statement
I’ve always believed the South isn’t just a place—it’s a feeling. There’s something about the wraparound porches, the soft drawl of a stranger saying “y’all,” and the smell of biscuits baking that just slows time. I created this itinerary for clients who wanted charm, culture, and connection—without long drives or constant packing. From sipping champagne under chandeliers in Charleston to ending the night with s’mores by the sea on Amelia Island, this route is about savoring the South the way it’s meant to be done: slow, sweet, and with a little bit of soul.
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Where to stay in the Southeastern US
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Things to do in the Southeastern US
A walking tour is the best way to see the sites and learn local history.
Take a carriage ride through historic Charleston
There’s nothing quite like seeing Charleston from the back of a horse-drawn carriage. It’s the perfect way to get the lay of the land while soaking up all the charm: pastel mansions, gas lamps, and secret garden gates. Tip: Go early in the morning before the heat kicks in and the streets fill with tourists.
Toast sunset at Hotel Bennett’s champagne bar
Perched at one of the city’s most elegant hotels, this sparkling little gem is where I always send clients to kick off a girls’ trip or anniversary night. Order the Queen’s Jewel cocktail (think glittering, blush-pink perfection) and enjoy the golden hour views over Marion Square. Even the bar snacks are chic.
Wander the moss-draped squares of Savannah
I always tell people Savannah isn’t a city you “do”—it’s one you feel. Walk through Chippewa Square with a coffee in hand, listen for the clop of horse hooves on cobblestones, and pause under the mossy oaks. Don’t miss Lafayette or Monterey Square—quieter and extra dreamy.
Get spooked on a Savannah ghost tour
Even skeptics love this one. On one of my favorite tours, our guide told us about the haunted mirror in the Sorrel-Weed House...and my phone mysteriously shut off. Coincidence? Maybe. But it definitely made me sleep with one eye open. Book a nighttime tour for full goosebumps.
Beach day on Tybee Island
Just 30 minutes from Savannah, Tybee has a laid-back, retro vibe that feels worlds away. Rent bikes, grab a cone from The Sugar Shack, and let the kids roam free. Pro tip: Head to the north end for dolphin sightings near the lighthouse.
Tour St. Augustine's Historic District
The oldest city in America feels like a European village, with narrow lanes, Spanish architecture, and centuries of stories. I always end up at Cousteau’s Waffle & Milkshake Bar for something sweet and over-the-top. Their Plimpton waffle with lemon curd and torched meringue is wildly underrated.
Kayak or paddleboard the marshes in Amelia Island
For families or couples wanting to get on the water, this is a peaceful, picture-perfect experience. We saw manatees, jumping fish, and the occasional heron just gliding by. Bonus: You can do a sunset paddle with a guide—ideal for golden hour Instagram shots.
Plan a spa morning at the Ritz-Carlton, Amelia Island
This spa is pure coastal luxury—think warm sea salt scrubs, eucalyptus steam rooms, and post-treatment tea in your robe overlooking the dunes. I tell clients to book this right before heading home—it’s the perfect ending to a relaxing Southern getaway.
Places to eat & drink in the Southeastern US
Breakfast is the most important part of the day. Fuel up with a Southern brunch before your big day exploring.
The Darling Oyster Bar – Charleston, SC
This is one of my go-to spots for seafood in Charleston. The vibe is vintage-chic, with marble counters and a raw bar that always delivers. I always start with a dozen oysters and the crab toast—trust me, it’s not optional. If you’re lucky enough to snag a window seat, order a martini and settle in.
Leon’s Oyster Shop – Charleston, SC
Don’t let the name fool you—the fried chicken is just as famous as the oysters. It’s casual, cool, and perfect for groups. The chargrilled oysters are addictive, and their frozen gin and tonics are a must on a hot afternoon. Bonus: they’re super kid-friendly and always buzzing.
The Grey – Savannah, GA
Housed in a restored Greyhound bus station, this is easily one of the best restaurants in the South. The menu is inventive but approachable. I still dream about the foie gras and grits, and the service is impeccable. Go early and grab a cocktail at the bar before dinner—the Art Deco interiors are worth lingering over.
Elizabeth on 37th – Savannah, GA
A Southern classic housed in a stately mansion, this place feels like a step back in time—but the food is fresh and current. It’s romantic and low-lit, with perfect service. Order whatever seafood special they have and don’t skip the warm bread basket. Ideal for a special occasion or anniversary night.
The Collins Quarter – Savannah, GA
Brunch here is a scene—and completely worth it. Think flat whites, avocado toast, and their famous short rib hash. I always tell clients to arrive by 9:30 am to avoid the wait, then walk it off through nearby Forsyth Park. Kid-friendly but stylish enough for couples.
Salt at The Ritz-Carlton – Amelia Island, FL
This is the ultimate date night or final-night-of-vacation splurge. The focus is on—you guessed it—salt, used in inventive ways to season and finish each dish. The setting is elegant but relaxed, with sweeping ocean views. The tableside steak carving and salt pairing is a conversation starter.
The Ice Plant – St. Augustine, FL
Part cocktail bar, part farm-to-table eatery, this place is tucked inside a restored 1927 ice factory. It’s moody, stylish, and perfect for a late lunch or nightcap. The shrimp and grits are top-notch, and the bartenders are true artists. Get anything with their house-crushed ice—it’s a whole experience.
Preserved – St. Augustine, FL
Tucked into a restored Victorian house in Lincolnville, this gem serves refined Southern fare with a side of charm. Their deviled eggs with crispy duck cracklings are reason enough to go. Make a reservation and sit on the porch—it’s like dining in someone’s (very stylish) home.
Need to know
Distances are easy: The charm of this trip is that each destination is just a short drive away—no long-haul road days or flight transfers required.
Southern hospitality: Locals are warm and helpful. Don’t be shy about asking for recommendations or stories. You’ll likely leave with a few new friends.
Pack light but smart: From beachwear to cocktail attire, the South loves to dress up for dinner. And always carry bug spray for summer nights!
Don’t rush it: The South operates on a slower rhythm. Embrace it. Linger over coffee, watch the sunset, and let the day unfold like sweet tea on a porch swing.
Travel Advisor
Ryan Ali
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