The Best Off-the-Beaten-Path Southern Getaways

There’s much ado about Charleston’s resurgent food scene, but another South Carolina town is poised to give the city a run for its money. In Greenville, restaurants like the second outpost of Sean Brock’s game-changing Crescent City staple Husk are upping the ante with seasonal farm-to-table menus. Don’t miss the braised beef shortrib or bacon-wrapped pork tenderloin at Soby's, a cool spot built inside an 1800s former cotton exchange that retains its original brickwork and wooden beams. Stay at the Hotel Domestique, in nearby Traveler’s Rest, where beginner and expert cyclers alike can explore the winding trails of the Blue Ridge Mountains in style.

Off Florida’s Gulf Coast, the tiny barrier island of Gasparilla is an idyllic escape free of traffic lights and other modern annoyances (bikes and golf-carts are the main mode of transport). What it does have are long, sandy beaches, sea-glass waves, and a restored 1890 lighthouse on shores known for shelling and tarpon fishing. The sunny guest rooms at the 1913 grand dame Gasparilla Inn, which has hosted the likes of John Singer Sargent, Henry DuPont, and the Bush clan, ensure a restful stay. Come sunset, venture into downtown Boca Grande to sip rumrunners on the harbor-front patio at Miller’s Dockside, then reserve a table at Temptation, a funky restaurant where the grouper comes from right off the boat.

New Orleans may get all the glory, but this 1702 gulf town is the real birthplace of Mardi Gras, a fact gleaned over an afternoon spent at the Mobile Carnival Museum. NoLa resembles its predecessor in other ways, too (see the Queen Anne buildings and cast iron balconies on Dauphin Street). If architecture is your fancy, head to Oakleigh, Bragg Mitchell Mansion, and other historic house museums for a glimpse into antebellum life. Gracious Fort Conde Inn is itself a restored 1836 home—the second oldest in town—complete with original artwork and era-appropriate antiques. Drop your bags, then sample modern takes on the celebrated Southern-Creole cuisine this place is known for, from deviled eggs to fried oysters, at The Noble South.

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To experience the romantic ideal of the Old South, look no further than one of the oldest settlements on the Mississippi River, where the trees drip with Spanish moss and the mint juleps are flowing. Hike the Natchez Trace to see the woodland trade routes that once connected Nashville to this colonial cotton capital on your way to Monmouth Historic Inn, a 19th-century mansion framed by sprawling gardens of magnolia trees and azalea bushes. A day spent exploring the historic house museum feels like a step back in time (tour guides at Rosalie wear traditional hoop skirts), as does a stroll through the atmospheric Natchez cemetery, with its live oaks overlooking the river.

The funky college town that produced bands like R.E.M. and the B-52s has a personality all its own, which is evident in the quirky shops and restaurants of its Victorian downtown streets. The racks at Dynamite Clothing are a vintage lover’s dream, while midcentury furniture enthusiasts might prefer the digs at Starlite Showroom. If shopping isn’t your thing, grab a peanut butter, banana, and bacon doughnut at Ike & Jane Café, bring your drinks into a movie at independent movie house Ciné, then grab dinner at The National, acclaimed chef Hugh Acheson’s Southern-Mediterranean hybrid. But music is the real draw here. Catch a live act at Georgia Theater, an Athens institution, then end your evening with the locals at Normal Bar.

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Oenophiles and historians will find plenty to love in C-ville, as the locals lovingly call it. The revolutionary vines of Thomas Jefferson’s Monticello have given way to more than thirty regional wineries where terraced hills of grapes resemble a miniature Napa Valley. Raise a glass of petit verdot at King Family Vineyards; the renowned Octagon blend is the order of the day at Barboursville Vineyards. Once you’ve exhausted your palate for reds, sample French small plates and let the bartender pick your poison at craft-cocktail den The Alley Light. But save room for dinner: C&O Restaurant serves farm-fresh French comfort food in a historic dining room overlooking its namesake rail lines. In the morning, fortify yourself with the Texas-style breakfast tacos at Brazos, then ride along the winding roads of Skyline Drive to see Shenandoah National Park in all its splendor.

At first glance, Chattanooga doesn’t appear to be Tennessee’s most vibrant cultural capital (Nashville is just two hours north), but the low-key art scene is quickly making the scenic city a must-visit. Sculptures encourage interaction at Main Terrain Art Park, and public art is also displayed in unexpected pockets throughout town. You can glimpse works by the likes of Robert Rauschenberg and Andy Warhol at the Hunter Museum of American Art, on a hilltop overlooking the Tennessee River. For a glimpse of under-the-radar local artists, opt for Southside’s Gallery 1401. The vivid midcentury-style Dwell Hotel makes an ideal base for discovering the offerings of the newly renovated Chattanooga Choo Choo rail station. At Stir, a designated ice chef hand-cuts cubes for seasonal craft cocktails that complement the New American cuisine. Across the street, the Chattanooga Whiskey Experimental Distillery is a cozy micro distillery and drinking den accented with old barrel staves.