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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!

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. But many don’t realize that Waynesville also adds so much to this NC region’s food roster! Hit both of these towns (and more) on a fabulous food road trip that could last a weekend or a week.

Stop 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 Chai Pani or the newly opened S&W Market that boasts a hall-full of local food vendors to choose from. Book dinner at Cúrate or Zambra (both Spanish and both incredible!). Top off the night with a meticulously crafted seasonal cocktail at Sovereign Remedies or a rooftop espresso martini and dessert at The Montford.

The Swag Waynesville

Even if you’re not staying at this Waynesville resort, The Swag offers dinner reservations for parties of six or fewer. Email [email protected] to inquire about availability. Image: The Swag | Facebook

Stop 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 and food-driven bed and breakfasts like The Swag, Andon-Reid, or Brookside Mountain Mist. The spot for fine dining in Waynesville is the 42-seat Chef’s Table, a lauded wine-centric restaurant with seasonal dishes and 250+ wines for pairing. For a more casual dinner option, farm-to-fork Frog’s Leap Public House serves up 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.

There are many ways to continue your food journey back to Asheville. Check out Oak Steakhouse at the new Skyline Lodge in Highlands, NC; explore the funky food town of Brevard, NC; or check off the bucket-list-worthy restaurant Postero in Hendersonville, NC.

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.

Pippin Hill Farm

Check the Monticello Wine Trail event calendar for special dinners, fall festivals, and live music happening while you’re there! Image: Pippin Hill Farm & Vineyards

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: The stretch of U.S. 250 between Charlottesville and Crozet is a beloved drive among locals, and you’ll see why as you head toward Veritas for an early lunch and tasting in a stunning setting. Then, book the full tour at King Family Vineyard — it’s one the best in Virginia — and enjoy a bottle on the grounds that 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 for you to create an itinerary based on the stops you choose. Check it out here to plan your road trip!

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 Cafe 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 that holds more than 14,000 graves of American vets.

Chalmetter Battlefiend

Note: As of September 21, 2021, many of the mentioned historical facilities have not reopened after Hurricane Ida, so be sure to check online before you plan your trip. Image: NPS

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 American’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 that 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 2: 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.

RELATED: Welcome to Natchez, MS, a Creative Utopia

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 lots of other activities like ziplining, archery, and dining.

Amicalola Falls

Amicalola State Park has dozens of hikes and outdoor outlets for everyone. Image: Fannin County Chamber of Commerce

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 towards beautiful Lake Burton. This one-mile hike leads through a verdant, boulder-filled valley the 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.

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, get a drink at Lagniappe‘s back patio, and share some mouthwatering small plates at Kyu.

Wynwood Walls Miami

Wynwood is an art lover’s dream! Image: Zoe Yarborough

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 tiny 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. Since 1978, this place has represented the Florida Keys lifestyle and 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: Once you make it to Key West, check into the whimsical Artist House bed and breakfast, a well-situated inn 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 Hemmingway Home & Museum to tour the famous author’s storied swimming pool, gardens, and grounds. Free to visit and with the best rooftop views of Key West is The Studios of Key West, a contemporary art center off Duval Street. They have a stacked program of art, theater, concerts, classes, and more.

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


Find more travel tips, weekend getaways, destination ideas and so much more in our “Travel” section. Click HERE.

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