This Is the Perfect Itinerary For a 6-Day Southern U.S. Road Trip

World-class Southern city Charleston anchors the route.

Can there be anything dreamier than a good ol’-fashioned Southern road trip. Spectacular scenery, some of America’s most beautiful small cities, a plethora of outdoor activities and foodie feasts, and back roads empty for miles. The open road is calling. Time to answer, y’all!

1.  Day 1: Asheville, North Carolina

Often compared to Austin or Portland, this liberal Southern enclave is nestled in the foothills of the Great Smoky Mountains, one of America’s original frontiers. And there’s plenty to do here, from mountain biking and kayaking to sampling microbrews and touring historic homes.

Asheville is just a quick two-hour drive from the region’s major hub of Charlotte, but you can also fly directly into Asheville’s smaller airport, which is about a 20-minute drive from town.

Book a room at The Windsor, a chic little hotel housed in a 1907 building with just 14 suites, each decorated with unique crafts from Paris and the local artistic community. 

You’ve just gotten to the South, so your first meal should, of course, be some delicious barbecue, and your best bet is Buxton Hall. Located in a former roller rink, this expansive eatery specializes in eastern-style Carolina barbecue cooked over oak and hickory coals and doused with vinegar-pepper sauce. Order a plate of local pasture-raised whole-hog bbq and all the fixings, including fluffy hushpuppies, stewed lima beans, smoky garlic-buttermilk mashed potatoes and braised collard greens with cider vinegar and black pepper. Wash it all down with a craft cocktail like the Wax and Wane with Beefeater gin, sherry, preserved pineapple, rosemary, lemon, sparkling wine and sumac for a kick.

Or, since Asheville is a mecca of craft brewing, simply slip into the Wicked Weed Brewing Pub on your walk home for an on-tap specialty like the Black Angel Cherry Sour or the Lieutenant Dank American Ale.

2.  Day 2: Asheville

The next morning, it’s up and at ‘em early for a hearty breakfast at Biscuit Head. Take your time deciding between downhome delicacies like the brisket biscuit with pickled onion, smoked chèvre, poached egg, and buffalo hollandaise; or the one with mimosa-fried chicken with sweet-potato butter, Sriracha slaw, and a poached egg.

That’ll be just the fuel you need for a walking tour of America’s largest private residence, the famous Biltmore Estate, as well as its well-tended gardens, hiking and biking paths, and even a quick visit to the on-property farm and winery.

You’ll make it back to town in time to take a quick look at some of the galleries in the River Arts District. This former industrial district on the edge of town is now home to local galleries showcasing everything from painting, ceramics, and sculpture to glassblowing and basket weaving.

Depending on how you’re doing for time, you might even want to stay down by the river and rent an inner tube from French Broad Outfitters for a lazy float down the stream. Better yet, stop by the New Belgium Brewery and tasting room on your way and pick up some seasonal brews so you can enjoy this riverine pastime like the locals do… with a cold beer in hand!

Keep it simple with a casual dinner at White Duck Taco Shop’s outdoor patio. The Korean beef bulgogi taco alone is worth the visit, though the Thai peanut chicken is a close second. If you just can’t kick a hankering for Carolina barbecue, though, you can also stop just around the corner at 12 Bones Smokehouse, which the Obamas always visit when they come to town.

Day 3: Charleston, South Carolina

The drive today cuts through the center of the state from the upcountry down to the coastal tidewater, and your destination is one of America’s colonial cultural gems, Charleston

There’s no shortage of charming hotels in the colorful city center, but for a taste of luxury par excellence, the must-visit property is the newly refurbished Belmond Charleston Place. Stepping into the ornate lobby, with its sweeping Georgian staircase set under an enormous crystal chandelier is like stepping back to a more genteel time.

The rooms here feature postcard-worthy city and harbor views, not to mention all-marble baths. The refreshed aesthetic includes a soothing new palate of silver and blue tones with burnished dark-wood furnishings that blend Continental sophistication with contemporary comfort.

Be sure to schedule some time for a pre-dinner drink and nibble at the Charleston Grill. The crab cakes with lime and tomato-dill vinaigrette are juicy, crispy perfection, and thanks to the restaurant’s Coravin system, you can sample some “bucket list” wines by the glass, including a 1999 Domaine de la Romanée-Conti Vosne-Romanée red Burgundy and the 2001 Gaja Langhe Sori Tilden. If you have time, you can indulge in one of the four individually themed tasting menus (though you can also mix and match).

Of course, Charleston is a foodie’s paradise, so you’re spoiled for choice. Arrive in time for lunch, so you can meander over to Leon’s Oyster Shop, in a quieter neighborhood just outside the main tourist area of town. Go light with the shrimp roll with horseradish may, celery, and herbs with crushed potato chips on top, or dive right in with the fried oyster sandwich with lettuce, tomato, avocado, and chili-laced comeback sauce.

Spend the afternoon on the water but getting the lay of the land with Charleston Harbor Tours. You’ll motor past the city’s historic Battery waterfront, see Fort Sumter from the water, and pass by the USS Yorktown and the soaring Arthur Ravenel Jr. Bridge.

You’ll disembark just in time to hightail it back up fashionable King Street for a rooftop aperitif at Stars, one of the most popular venues in town, for a drink before dinner down the block at the new The Darling Oyster Bar. Seafood is the draw here, and once you taste the king crab parfait with layers of sweet meat, avocado, grapefruit, and herb pistou served with sourdough crostini, you’ll understand why. Other highlights on the menu might include cheddar grits with plump local shrimp, crispy Brussels sprouts, flecks of smoky country ham, and fennel; and oyster spaghetti with bacon, breadcrumbs for texture, earthy celery root, and tangy lemon-caper butter.

Day 4: Charleston, South Carolina

Spend the day soaking in a bit of history by booking a brief walking tour with Bulldog Tours. You’ll learn about Charleston’s 400-year past and the fascinating characters that made appearances on the scene here, not to mention gett a peek at some of the city’s most gorgeous churches, houses, and gardens.

Afterwards, you’ll need to hop back in the car to trek out to one of the stately plantations that ring the city. Boone Hall is an exceptional option in Mt. Pleasant. Though the current house dates only to the early 20th century, the plantation itself was first established in 1743. There are a variety of tours, from a quick house tour to a property drive in one of the large ATVs, not to mention cultural exhibits and lectures. The plantation is a revealing look into the South’s past and the bleak history of slavery. 

Maintain social conscience as the theme of the day by dropping into a new King Street boutique called Ibu, with which Southern Charm’s Landon Clements is involved. The store works with communities in Africa and Asia to source sustainable, fair-trade apparel and crafts. 

This evening, stick to East Bay Street near the waterfront and start with a cocktail or glass of chilled white wine at one of the town’s prettiest rooftop bars at the Market Pavilion Hotel, which overlooks the historical Customs House. From there, it’s just a quick walk north a few blocks to one of the city’s best raw bars at 167 Raw. Depending on the season, you’ll find selections of oysters sourced from up and down the Eastern Seaboard and well as more local specialties like succulent Jonah crab claws. For a main, you need to order the signature tuna burger. Sushi-quality yellowfin is ground and shaped into a patty, then flash-seared on the outside for some texture and served on a fluffy house-made bun with guacamole and arugula, as well as a helping of chips and a pickle spear.

Day 5-6: Palmetto Bluff, South Carolina

After a busy few days in Charleston, it’s time for some R&R before the trip home, and the place to get it is off-the-beaten-path Palmetto Bluff. Lower key than nearby Hilton Head, but still within easy distance of Savannah, Palmetto Bluff is a gated enclave with a resort run by luxury brand Montage right on its waterfront. The hotel is actually preparing to open an entire new section in September that will almost double its room count, though you wouldn’t know it to walk around the place thanks to a thoughtful layout. 

Rooms here include palatial bath suites and living rooms with fireplaces just perfect for curling up in the evenings. Then again, sitting on your own private patio or porch as a gas lamp flickers overhead and a sultry breeze picks up, you fully get the sense that you’re in a special part of the South.

This piece of land is truly a treasure. Historically, there were about a dozen plantations on the property. But today, the resort’s land and water conservation efforts include rigorous, hands-on management to ensure this delicate tidal ecosystem and its many indigenous species remain intact.

Your days here can be spent cycling the idyllic paths, renting boats to ply the placid waters, or just lazing around the pool or in the spa. Be sure to book a kayak around dusk so you can paddle out to a nearby sandbar at low tide and watch as pods of dolphins swim by on their way out to sea. You can also spend an afternoon being boated to the Bluffton farmer’s market and stocking up on local produce and some mouthwatering baked goods while a band plays on the little town square.

Get “off-campus” for a laidback lunch at folksy Cahill’s Market.

The specialty here is fried chicken, and plates come with a choice of classic Southern sides like cheesy broccoli casserole, sweet-potato soufflé, okra, and tomatoes, fresh South Carolina peach slices, and homemade pickled beets. Afterwards, peruse the shelves for local artisanal goods like pickled vegetables and wild honey. 

Back at the hotel in the evening, simply wander over to the screened-in porch at the River House for casual fare like peach salad with burrata, red mustard greens, basil, and aged balsamic; sweet corn agnolotti with fennel, roasted red peppers, and fine herbs; and creamy shrimp and grits served with strips of crispy bacon, fresh tomato, and microgreens. A specialty River House honey-ginger-lemon Manhattan prepared with house-made bitters wouldn’t go amiss either.

For something a little more refined, be sure to book a dinner at the resort’s signature Canoe Club. Start with the (mildly dangerous) Artillery Punch. It’s kind of like the South’s answer to Long Island iced tea, but if you can get the barman to divulge his recipe, you deserve a CIA commission.

The menu here is a mélange of regional and international ingredients prepared with a deft touch. Starters include jumbo lump crab with steelhead roe, grilled pineapple, and pickled shallots; and yellowfin tartare with caviar, quail egg, lime crème fraiche, and fingerling potato chips. Among the mains, the standouts include grilled cobia fish with white shrimp, Sapelo Island clams, Andouille, and sweet corn in an Old Bay broth; and Maine lobster wrapped in crispy katifi pastry with asparagus, citrus, and yellow tomato vinaigrette. For dessert, there’s grilled local cheese with fresh sliced peaches and cherries. A little sweet, a little savory, fully satisfying… it’s the perfect last taste of the South before the end of your trip.

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