From Historic St. Augustine to Enchanting Oxford — Don’t Miss These 8 Sweet Southeastern Cities

The South leads travelers on a winding journey — along bourbon trails, shrimp trails, hiking trails, and waterways galore. Visitors encounter surprises, too, from an UNESCO-listed university to the nation’s oldest city. Here’s a guide to popular attractions and traveler tips for eight of the most exciting Southeastern cities.

1. St. Augustine, Florida

Now this is a coastal escape with character: South of Jacksonville on Florida’s northeast coast, St. Augustine is the oldest continuously occupied European settlement in North America. Spanish settlers arrived in 1565 and ruled until 1821, when Florida became a US territory. In the late 1800s, oil magnate Henry Flagler turned St. Augustine into a vacation destination with his grand Spanish Renaissance Revival-style retreats for wealthy northerners. The city’s Old World vibe remains within a 144-block Historic District, which attracts 6 million people annually.

No visit to St. Augustine is complete without a stop at the Castillo de San Marcos National Monument, the 17th-century stronghold built by the Spanish to ward off pirates and other invaders. At the Fountain of Youth Archaeological Park — where Juan Ponce de León allegedly discovered the famous “anti-aging” springs in 1513 — sightseers can sip straight from the sulfur-laden source. After dark, tour guides lead travelers to haunted saloons, shops, and lighthouses where spirits are said to still linger.

Other diversions include the eclectic Victorian-era art collection at the Lightner Museum (inside what used to be the Henry Flagler-designed Alcazar Hotel); funky boutiques, antique shops, and art galleries on St. George Street, plus an array of restaurants serving Southern staples, Cuban fare, and fresh seafood.

A short drive away, Anastasia State Park and St. Augustine Beach lure travelers to unspoiled nature and beautiful beaches. St. Augustine is a rare Floridian gem — a city steeped in history that also has a refreshing amount of modern appeal.

Travel Tips

The nearest major airport, Jacksonville International Airport, is a 55-minute drive away. Rent a car, especially if you’re planning to visit the beach. Old Town Trolley Tours offers hop-on, hop-off sightseeing packages, and Ghost Tours of St. Augustine is known for its haunted trolley tours and pub crawls. Stay in the Historic District; options range from the quaint St. Francis Inn to the luxe Casa Monica Resort & Spa.

2. Gatlinburg, Tennessee

Gatlinburg is most famous for being the primary gateway to the country’s most-visited national park, the Great Smoky Mountains, which welcomed over 14.1 million people in
2021. But the town itself is also a worthy destination, mixing down-home Southern charm, big-mountain pride, and small-business enthusiasm. A bevy of craft breweries and distilleries have started up in recent years, including the Doc Collier Moonshine Distillery, purveying hootch made with mountain-stream water and corn whiskey.

The area is also home to the Great Smoky Arts & Crafts Community, the country’s largest concentration of artists and craftspeople. Along this 8-mile loop just off the East Parkway, visitors can peruse galleries that showcase pottery, quilts, tapestries, paintings, woodworks, baskets, furniture, blown glass, and more. For lunch, the Wild Plum Tea Room serves an ever- changing menu that can include sherried tomato bisque, salmon burgers, vegan offerings, and homemade desserts.

Just a mile south of town, the wilderness of Great Smoky Mountains National Park is highly accessible to visitors, with 800 miles of trails suited to everyone from beginners to long-distance backpackers. One of the most scenic hikes is up Mount LeConte, where the vista-studded 5.5-mile switchback route leads up to the sixth-highest peak east of the Mississippi River.

The easiest way to witness the beauty — and see the mountaintop haze that gives this range its name — is to get high… on a ridgetop road, that is. The Foothills Parkway is 72 miles of winding road, with epic views of the surrounding peaks, green wilderness and, on clear days, even the town of Gatlinburg itself.

Travel Tips

It’s hard to visit Gatlinburg and not want to stay in a log cabin. A slew of rental companies, including Cabins of the Smokies Rentals and Cherokee Orchard, can connect you with hideaways with one to 20 bedrooms, all with that cozy, retreat feel. Hit up NOC Gatlinburg for hiking boots, camping supplies, or bike rentals. Or stop by the Smoky Mountain Angler to pick up a fly-fishing tie or two, and find out what’s biting where.

3. Bardstown, Kentucky

Nestled between Kentucky’s twin big cities of Louisville and Lexington, Bardstown is the Bluegrass State at its most idyllic, with a picturesque Main Street, historic landmarks, and Southern charm made all the sweeter by the local industry of distilling. Some of the state’s most revered bourbon labels call this town home, from big names like Maker’s Mark to family-operated stillhouses that continue to revere the spirit that was born — and perfected — in this part of the country.

Though it may seem like bourbon is flowing from every spigot in town, there’s more to Bardstown than booze. Settled in 1700, this small city of 13,000 is one of Kentucky’s oldest, and it has the rich history to prove it. Its biggest attraction is My Old Kentucky Home State Park, where composer Stephen Foster penned his anti-slavery ballad, “My Old Kentucky Home, Good Night,” in 1852. And more than 300 other local buildings appear on the National Register of Historic Places, including the early 18th-century Basilica of St. Joseph Proto-Cathedral.

The Bourbon Capital is also expanding its spirited reputation into the culinary arts, with must-try experiences like My Old Kentucky Dinner Train, a scenic dining tour aboard a restored 1940s rail car, and The Rickhouse, where bourbon finds its way into everything from the salmon to the chocolate bread pudding.

Travel Tips

Bardstown’s famous Kentucky Bourbon Festival traditionally takes place in September every year — but you don’t have to wait till fall to sample the beloved spirit. Drive the Kentucky Bourbon Trail to see the area’s finest distilleries in a single day, from Jim Beam up north to Maker’s Mark just a few miles south. Skip the town’s mediocre hotel selection, and instead head to one of its authentic B&Bs set in historic buildings that date back more than 100 years. Best among them is the Bourbon Manor B&B, located in two well-preserved plantation-style mansions and featuring a smokehouse and — of course — a bourbon bar.

4. St. Simons Island, Georgia

Only four of Georgia’s 15 coastal islands are accessible by car, and of them, St. Simons is king. Home to the largest year-round population of residents (just under 15,000), it offers the best of both worlds: the scenery of a wild, natural place mixed with perks like coffee shops, yoga studios, and upscale restaurants.

Residents and visitors alike come to admire the marsh and waterfront. One of the best and easiest ways to pay homage is from a kayak. Local guides point out island wildlife, from herons to oyster catchers, dolphins to minks, while timing two-, three-, and four- hour paddle trips to make the most of the tides.

Those who want an even wilder scenic experience can book a day trip to the satellite Little St. Simons Island, a private resort. Packages include transport from the main island, an experience guided by one of the resort’s naturalists, and lunch, plus time on 7 miles of private beach. After a day of exploring, locally owned Southern Soul Barbecue serves up all the favorites: ribs, pulled pork, burnt ends, and pimento-cheese sandwiches.

Travel Tips

The only hotel located on the waterfront is The King and Prince Beach & Golf Resort, a five-minute drive from Pier Village, the largest center for retail, restaurants, and tour operators like Southeast Adventure Outfitters. The beach on St. Simons is one of the best in the South for riding bikes. Bring yours, or rent wheels from Ocean Motion, which caters to all riders — even younger kids who need a Tug-a-Bug add-on seat.

5. Beaufort, South Carolina

There’s a reason why first-time visitors to Beaufort often feel a sense of déjà vu within moments of their arrival: The moss-draped oaks, antebellum mansions and winding salt marshes have appeared in dozens of films, including Forrest Gump, The Big Chill, and The Prince of Tides.

The grandest old homes — built for the region’s wealthy planters — are located in the Old Point neighborhood, which overlooks an ever-changing mosaic of tidal creeks, salt flats, and palmetto-dotted islands. Just a short stroll away, Bay Street bustles with boutiques, galleries, and restaurants like Saltus River Grill, whose waterfront patio fills each evening with locals sipping wine, nibbling fresh shrimp, and swapping stories. Younger and trendier, Old Bull Tavern serves creative small plates, bourbon flights, and frozen craft cocktails in an unassuming brick building.

Beaufort has harbored many famous residents over the years, including Tom Berenger, Ted Turner, and John Mellencamp, but none was more beloved than author Pat Conroy, who beautifully described his adopted home in his works. Opened in 2016, the Pat Conroy Literary Center offers a glimpse into the writer’s life.

A kaleidoscope of sea islands surrounds Beaufort. Some, like Daufuskie and St. Helena Island, have become centers of African American Gullah culture; others, such as Hunting Island and Fripp, front the Atlantic Ocean and are rimmed with beaches.

Travel Tips

Exploring the warren of waterways that surrounds Beaufort by kayak is one of the great hidden pleasures of the city. Rivers flow past old plantations, historic forts, and napping alligators; closer to the ocean, hundreds of bottlenose dolphins make their home in deep briny creeks. Beaufort Kayak Tours conducts dolphin, history, and ecology excursions, while Beaufort River Tours takes guests out to see dolphins on a larger boat. Cool off at low tide, when tiny sandbars emerge to create impromptu beaches.

6. Cedar Key, Florida

Still-working fishing villages are a rare find in Florida, yet Cedar Key — a 2.5-hour drive north of Tampa — is precisely this, serving up a timeless vibe on its crab-trap-laden docks and in its weathered-wood restaurants and bars balancing on stilts over the Gulf of Mexico.

Along the bustling waterfront, amateur anglers rub elbows with locals who work the day boats hauling in redfish, trout, and shellfish. And beyond the coast, the island is a natural paradise beloved by both cyclists and kayakers. The destination also offers motorcyclists 13 miles of open road along three keys. Bikers relish the ride into and out of town as well, past wetlands, agricultural fields, and scrub forests.

Riders who pedal their own two wheels can cruise the Cedar Key Railroad Trestle Nature Trail for water views and sightings of coastal-dwelling birds like anhingas and ospreys. Nine miles away, many cyclists also target the Shell Mound Trail, which provides a glimpse into the life of the Timucua Native American tribe from 1,000 years ago.

Kayakers have the most real estate for exploring, weaving between a number of islands formed by the delta where the Suwannee River meets the Gulf.

Regardless of how visitors get out and mix with the island’s wildlife, wetlands, and trails, they can’t help but settle into the calm, lost-in-time ambience found only on Cedar Key.

Travel Tips

Don’t miss the Tiki Bar Behind Low Key Hideaway, one of the best old Florida remnants still standing. The wood walls prop up a collection of license plates and colored glass bottles. Order a Bloody Mary, heavily garnished with shrimp, olives, pickled jalapeños, and a pickle. For dinner, pop over to 83 West — two eateries sharing one roof; upstairs, the more upscale 29 North serves steamed local clams, bacon-wrapped scallop kabobs, and Coca-Cola baby back ribs. Look to Kayak Cedar Keys for rentals and quick lessons on reading the tides.

7. Charlottesville, Virginia

Thomas Jefferson was good at most things he attempted, but making wine wasn’t one of them: In 1773, after devoting 2,000 acres of land near Charlottesville to vineyards, he tasted what little he’d produced and admitted defeat. Tenacious Virginians kept at it though; today, more than two dozen Charlottesville-area wineries turn out delicious, award-winning wines year after year. One to try is Gabriele Rausse, a hip, friendly tasting room that’s tucked into a forested glen. More Uber-friendly is Wineworks Extended, winemaker Michael Shaps’ in-town tasting room.

Jefferson was never able to convert his love of wine into a successful DIY project, but Monticello, his Charlottesville home, overflows with other triumphs, from the iconic dome he designed to the hundreds of varieties of fruits and vegetables he cultivated. Secrets abound as well, from a windowed playroom hidden in the rafters to a spot on the back deck that offered Jefferson a direct view of his beloved University of Virginia just 5 miles away.

Even non-UVA grads will enjoy a tour of the campus, with its Jefferson-designed Rotunda and grassy Academical Village, which comprises the original university. Nearby, the car-free downtown mall is strewn with boutiques, restaurants, craft breweries, and a wonderfully inordinate number of bookstores, including the quirky Daedalus Bookshop.

Travel Tips

This part of Virginia is particularly gorgeous during spring and fall, but be sure to check the UVA calendar for home football games, parents’ weekends, and graduation, which fill the city to overflowing. Tours of Monticello book early, so plan ahead and consider upgrading to one of the special-interest tours like “Behind the Scenes” and “Slavery at Monticello.” Miles of hiking trails and wheelchair-friendly pathways also loop through the property. Downtown, dine at French-inflected C&O Restaurant, which counts on Virginia sources for wine, cheese, fish, produce, and other foods.

8. Oxford, Mississippi

When the founders of Oxford settled on the name — yes, in honor of the UK–based school — they did so in the hopes of landing the state university. In 1844, that dream came true, marking the beginning of the town’s reign as a — if not the — cultural hub of Mississippi.

Like most college towns, Oxford is home to a few outstanding independent bookstores, most notably Square Books, which houses an impressive collection of works by Southern authors, as well as books about the South. The store also puts on more than 150 author events each year and celebrates the area’s literary greats, which have included John Grisham and William Faulkner (whose history-filled estate, Rowan Oak, is located a five-minute drive from downtown).

Beyond literature, the city is known for a long-standing tradition of great blues music. Rooster’s Blues House, part of the Mississippi Blues Trail that honors the legends and history of the art form, hosts live music every weekend. Proud Larry’s, another local favorite, dishes up comfort-food favorites such as jambalaya, pastas, and pizzas by day, and showcases up-and-coming musical acts for less than $10 a ticket by night.

The city’s food scene has long been heating up. One of its biggest success stories is the James Beard award–winning City Grocery, known for its elevated take on Southern cuisine, such as shrimp and grits and red grouper collar and belly with pickled sweet peppers. For down-home eats, Mama Jo’s fried chicken, mac-and-cheese, and pecan pie are dished up with love, pride, and an education on all things Southern.

Travel Tips

Stay at the Graduate, a hip downtown boutique hotel found along the Square. The 136 rooms pay homage to the local writers and musicians who’ve made the city so rich in culture. Rise early enough for breakfast at Cabin 82, the hotel’s café serving beloved fare from fried chicken to buttermilk biscuits. You’ll also want to linger over a craft cocktail at The Coop rooftop bar while enjoying the city lights.

A version of this article appeared in our partner magazine, America’s Best Small Towns, in 2022.