We love that the great American road trip is making a comeback in the hearts of travelers in the South and beyond. To help inspire your next big adventure, we’ve created five road trips for different travel personalities. Whether you prefer to plan your route around culinary pursuits, sipping regional wine, hiking to waterfalls, brushing up on American history, or feasting on visual arts, we have an itinerary for you!
Use these links to skip straight to your preferred travel focus.
FOR THE FOODIE
Asheville, NC > Waynesville, NC
Lovingly called a “Foodtopia” of the South, Asheville has no shortage of award-drenched restaurants to choose from, from eclectic cafes to cozy breakfast spots. Waynesville also adds so much pizazz to this NC region’s food roster! Hit both of these towns on a fabulous food road trip that could last a weekend or a week.
Day 1
Book a hotel room downtown and start the day with coffee from Trade & Lore and a table-spanning breakfast spread at Early Girl Eatery. Work your appetite back up by exploring all that Asheville has to offer (we have a whole itinerary for you HERE) — from dozens of breweries and downtown’s Grove Arcade shops to the Grove Park Inn and the Biltmore.
Make your way back to town for lunch at the open-air, locally loved All Day Darling. Book dinner at Cúrate for Spanish tapas or Asheville Proper for the best steak of your life. Top off the night with a meticulously crafted mezcal or tequila cocktail at newly opened Anoche.
Day 2
About 40-ish minutes away is Waynesville, an unassuming small town with a prolific food scene. Check into one of the town’s luxurious, food-driven bed and breakfasts like The Swag, Andon-Reid, or Brookside Mountain Mist. The spot for fine dining is the 42-seat Chef’s Table, with its seasonal dishes and 250+ wines for pairing. For a more casual dinner option, farm-to-fork Frog’s Leap Public House serves innovative, rotating Southern dishes highlighting a slew of local farmers. On your way out of town, pop into Kornerstone Kafe for a burger or The Patio for a sandwich.
FOR THE WINE AFICIONADO
Charlottesville, VA > The Monticello Wine Trail
Virginia is home to more than 300 wineries and dozens of wine trails, each with breathtaking scenery and quaint surrounding small towns. Charlottesville is the perfect home base for your exploration of the 35-stop Monticello Wine Trail. Between wine tastings, walk the immaculate grounds of the University of Virginia, and explore Main Street and the downtown pedestrian mall.
Day 1
On the first day, show up thirsty and hungry to Pippin Hill Farm & Vineyards, arguably the most popular stop on the trail. From the delicious food menu to the hydrangea-lined stone patio, it’s nothing short of charming and photo-worthy. From there, head to the funky and design-centric Blenheim Vineyards, owned by Dave Matthews of Dave Matthews Band.
On your way back to C-ville, stop at Jefferson Vineyards to taste the state’s best-known varietal, Viognier, and then tour Thomas Jefferson’s large historical estate, Monticello. After an afternoon siesta, take a sunset stroll through Barboursville Vineyards before eating at their adjoining restaurant Palladio.
Day 2
Head toward Veritas for an early lunch and tasting in a stunning setting. Then, book the full tour at King Family Vineyard — one of the best in Virginia — and enjoy a bottle on the grounds, which often hosts polo matches and musical events. The final stop is the small-scale winery, Stinson Vineyards, intentionally built into a three-car garage with 360-degree mountain views. End your day with dinner back in Charlottesville at Ivy Inn.
The Monticello Wine Trail has the niftiest online tool to create an itinerary based on your chosen stops. Check it out here to plan your road trip!
FOR THE HISTORY BUFF
New Orleans, LA > Vicksburg, MS
There are so many historical landmarks in the Deep South. This route from New Orleans up through Louisiana and Mississippi is filled with historical importance across many eras and wars and will be fascinating whether you’re history-minded or not.
Day 1
Start the day by walking through New Orleans’s French Quarter and Jackson Square. The Louisiana State Museum has a network of five historical museums in New Orleans, including The Cabildo, the site of the Louisiana Purchase transfer ceremonies in 1803, and one of Louisiana’s most significant historical buildings.
After coffee at Café Du Monde, drive to Chalmette Battlefield, the site of the Battle of New Orleans in 1815. This site contains a reconstructed American rampart, an 1830s house, a 100-foot-high monument, and the Chalmette National Cemetery, which holds more than 14,000 graves of American vets.
From here, drive the Great River Road along the Mississippi River toward Baton Rouge through New Orleans Plantation Country. This 54-mile stretch is home to 10 moss-drenched plantations, including Oak Alley, whose exhibits and tours educate about America’s darkest chapters.
If you have time, head to the capital of Cajun Country, Lafayette, home to the 23-acre living history museum and folklife village Vermilionville which celebrates Acadian, Creole, and Native American cultures from 1765 to 1890. End the day in Baton Rouge with a visit to the splendid art deco Louisiana Old State Capitol and book a room at The Stockade Bed & Breakfast, named after the Civil War stockade that occupied the grounds.
Day 3
From Baton Rouge, head north to explore the Port Hudson State Historic Site in Jackson, LA, where the Siege of Port Hudson occurred in 1863. Keep heading north to Natchez, MS, to walk their beloved cemetery and take the famous Pilgrimage Tour of the town’s gorgeous architecture and historic homes and gardens.
On your way to Vicksburg, stop at Emerald Mound, the second-largest ceremonial mound in the country, built and used between 1200 and 1730. This history road trip will fittingly culminate at Vicksburg’s National Military Park, a crucial military site that led to the Union’s control of the Mississippi River.
FOR THE WATERFALL CHASER + TRAILBLAZER
Atlanta, GA > Rabun County, GA
North Georgia is rich in stunning fall foliage, pristine lakes, impressive waterfalls, and scenic hikes. This road trip would make a fabulously fun one- or two-day trip from bustling Atlanta. These trails are relatively short (two are 0.4 miles round-trip and two are two miles round-trip), and the connecting drives are breathtaking.
Stop 1
Head 70 miles north of Atlanta to Amicalola Falls State Park, home to a magnificent 729-foot waterfall. A one-mile hike leads you to the falls, and the park boasts many other activities like zip lining, archery, and dining.
Stop 2
Another 40 miles takes you to Helton Creek Falls in the Chattahoochee National Forest near the quaint town of Helen. An easy 0.2-mile hike leads to two more stunning cascading waterfalls. From here, grab lunch at a charming cafe in Helen.
Stop 3
From Helen, Hemlock Falls is another hour’s drive toward beautiful Lake Burton. This one-mile hike leads through a verdant, boulder-filled valley that meanders alongside the babbling Moccasin Creek to multiple waterfalls and sweeping lake views.
Stop 4
It’s just a 10-minute drive to the last hike of the day, Minnehaha Falls. This one is on Lake Rabun, and the short but sweet 0.2-mile trail has a spectacular payoff! With some of the most beautiful views in Georgia, it’s an excellent way to end the day.
From Minnehaha, it’s about an hour and 45 minutes back to Atlanta, where we suggest booking a night at the posh Kimpton Sylvan Hotel in Buckhead or the Wylie Hotel so you can easily walk/run/bike the ever-expanding Atlanta BeltLine and see all that’s new from Ponce City Market rooftop to Krog Street Market and beyond.
FOR LOVERS OF THE ARTS
Overseas Highway from Miami > Key West
The Overseas Highway from Miami to Key West is a modern wonder and one of the great American road adventures. It spans over 100 miles, crosses 42 bridges, connects 34 islands, and passes mangrove trees, coral reefs, quaint island towns, and historical sites. Fly into Miami, rent a convertible, and get ready for a feast for every art lover’s eyes!
Day 1
Check into a posh hotel in Miami’s Brickell neighborhood. Head to the Pérez Art Museum, a sleek, waterfront modern and contemporary art museum that will blow you away. In the late afternoon, head to the Wynwood Walls & Arts District, famous for its jungle of massive and colorful painted walls, lively nightlife, and a melting pot of cultural influence. Pop into Bakehouse Art Complex, grab a drink at Lagniappe’s back patio, and share some mouthwatering small plates at Kyu.
Day 2
Pack the car and head South to the Vizcaya Museum & Gardens, a historic 1914 mansion-turned-museum with 10 acres of gardens, art, sculptures, grottos, and more. As you start the drive to Key West, stop at Coral Castle Museum in Homestead. Built over 30 years by one man, it’s a mysterious stone sculpture garden with lots to see. Past Key Largo, a 30-foot giant spiny lobster, Betsy, will tell you you have made it to Rain Barrell Village, which represents the art of more than 500 local artists. Once you get to Islamorada, check into Cheeca Lodge and take a load off!
Day 3
Islamorada is home to the Morada Way Arts & Cultural District, a compact neighborhood filled with sculpture galleries and art studios. If you can, visit on the third Thursday of the month when local artists, musicians, and food vendors come together for a lively art crawl.
Day 4
In Key West, check into the whimsical Artist House bed and breakfast built in the late 1800s by a painter and a jazz pianist. Home to the famous Key West Film Festival, the town also has a retro, non-profit movie theater called Tropical Cinema that plays both independent and blockbuster films. Visit the 1930s-built Hemingway Home & Museum to tour the famous author’s storied pool, gardens, and grounds. Free to visit and boasting the best rooftop views of Key West is The Studios of Key West, a contemporary art center off Duval Street.
When it’s time to drive back to Miami, if there’s time, hit some of the US 1 stops you missed on the way down, including the area’s two National Parks.
StyleBlueprint has a treasure trove of road trip ideas in these articles that we urge you to revisit!
The Best Drive in America
The Southern Road Trip All Music Lovers Should Take
5 Southern Weekend Getaway Ideas
5 Bucket List U.S. Road Trips Everyone Should Take
Explore 30 Miles of Handmade Pottery
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Find more travel tips, weekend getaways, destination ideas, and so much more in our “Travel” section. Click HERE.
