The Most Charming Southern Road Trips
By Kellie Walton
There’s nothing quite like loading up on your favorite snacks, packing the car down with suitcases, and heading out on a road trip. The landscapes of the south lay claim to the perfect backdrop for a trip like this, with winding roads, small towns brimming with adventure waiting to be discovered, and big cities interspersed rich in both history and personality. If a road trip is on the itinerary this year, we’ve put together itineraries for three perfect options, complete with activities, lodging, and dining recommendations.
Leiper’s Fork, Tennessee
Leiper’s Fork is one of Middle Tennessee’s most cherished, and yet worst-kept secrets. It’s a town marked by gravel roads and farmland that’s manicured in an aspirational way. Opt for a road trip to Tennessee’s center, hitting hotspots like Nashville and Franklin on your way in. But, we encourage you to set up camp in Leiper’s Fork for the duration, you won’t regret it.
Activities
Even though this town may be small, there’s plenty to keep you busy during your visit. On day one, stroll the village for shopping and sightseeing at spots like the David Arms Gallery, the Pick-If Fence, and Studio Bee Design. Once you’ve maxed out your credit cards, head out for a bike ride down the scenic Natchez Trace Parkway (a road trip destination in and of itself). Head north toward Nashville, where you’ll cross the iconic Natchez Trace Bridge towering 145 feet in the air. Round out your evening at Fox & Locke, a locally-loved live music joint, for a meat and three and renowned artists taking the stage.
On day two, spend some time exploring nearby parks like Garrison Creek Park and Timberland Park for hiking and picnics. After a day of energy exertion, take a load off at Leiper’s Fork Distillery for a tour and whiskey tasting. The stunning property has been in operation since 2016 and has become a beloved staple in the area.
We know you won’t want to leave, but on your last day, spend time horseback riding at the Natchez Trace Stables and picking out fresh produce from the Leiper’s Fork Farmers Market.
Lodging
If you’re looking for a hotel that exudes as much charm as Leiper’s Fork does, book a room at the Leiper’s Fork Inn, bookable on Airbnb. These two 100-year-old historic homes have been beautifully restored and are ready to welcome guests starting around $500 per night. If you’re looking for luxury, the brand new Southall Farm & Inn is as good as it gets. The luxury resort hosts a variety of onsite activities, stellar dining options, and a fabulous spa for plenty of R&R. If you’re balling on a budget, consider looking in the cities of Brentwood or Franklin located nearby.
Dining
Indulging in Southern food is one of the best parts of a road trip, and Leiper’s Fork will not disappoint. Visit locally-loved Country Boy for a breakfast spread ranging from cheese-filled omelets to a traditional collection of eggs, bacon, biscuits, and gravy. For lunch or dinner, Fox & Locke’s meat and three menu is a must. Elevate your experience with a wine tasting at Wines in the Fork, where you can (occasionally) taste wines on the banks of the Harpeth River.
visitfranklin.com
Cedar Key, Florida
If you’re a fan of oysters, this road trip destination is for you. Cedar Key is a small fishing village that deviates from Florida’s typical touristy beach towns, but there is no shortage of activities packed in the little city.
Activities
Spend time exploring the Cedar Keys National Wildlife Refuge, which provides a safe haven for wildlife all across the region. The refuge comprises 13 islands. For a deeper dive into history, visit the Cedar Key Museum State Park, complete with salt marsh breezes and towering trees. At sunset, head to the Dock Street Overlook for an impressive view.
Book a boat with Cedar Key Paddling and spend the morning kayaking on day two before drying off and heading to the Cedar Key Historical Society Museum to tour historic buildings packed with artifacts.
On your last day, soak in the beauty of the area by relaxing on Cedar Key Beach, booking a bird watching experience through Tidewater Tours, or admiring local art at the Island Arts Gallery.
Lodging
Opt for a B&B on your visit to Cedar Key, we recommend Cedar Key Bed & Breakfast as an incredibly charming option. If you’re looking for a touch more luxury, rent a stunning beachfront condominium or a room from The Island Place at Cedar Key. For a more budget-friendly option, the Harbor Master Suites sits right on the water.
Dining
Get your seafood fix for breakfast, lunch, and dinner, with plenty of options around the island. Kick off your days at the Annie’s Cafe, which may be unassuming from the outside, but is sure to make an impression. For lunch, grab an outdoor table at Tony’s Seafood Restaurant (the clam chowder can’t be beat). At nightfall, head to The Island Room Restaurant at Cedar Cove for plenty of elegant seafood offerings.
visitflorida.com
Savannah, Georgia
Time moves a little slower in Savannah, Georgia, making it the perfect destination for a low and slow road trip. Head into this historic city for a charming (and sometimes spooky) adventure.
Activities
On your first day, embark on a historic trolley tour that teaches you everything you need to know about the city’s impressive history. Jot down your favorite locations, then return to spend more time there when you wrap. We know Forsyth Park will be on that list, so make plans to wander beneath the massive oak trees and marvel at the stunning fountain in the middle. At night, get a little spooky with a ghost tour through the massively haunted town.
Head to the river for day two, where you can spend plenty of time wandering River Street to the tune of live street music. Make a pit stop at the JW Marriott to explore the free museum and gallery housed in its lobby, then round out your day by boarding the Georgia Queen, a riverboat that draws a collective gasp as it makes its way down the river running through the city.
On your third day, keep the road trip vibes going with a journey to neighboring Tybee Island, an adorable beach town. You can spend your time lounging on the beach, but be sure to visit the Tybee Island lighthouse for photo ops and a sprawling view of the town below it. As the sun begins to set, head out on a dolphin tour with a local tour operator like Tybee Dolphin Adventure.
Lodging
There are no shortage of places to stay in historic Savannah, but one of the most charming options is The Desoto, an opulent option in the heart of it all. If you prefer a stay on the water, book the River Street Inn, which is equal parts luxe and historic. For a budget-friendly option, look at the Foley House Inn.
Dining
You can’t go wrong with any restaurant in Savannah, as its food has been a draw for decades. But, we recommend starting your day at the Maple Street Biscuit Company for towering biscuit stacks. Save room for lunch, though, because the Olde Pink House cannot be beat. The line forms early, so it’s best to snag a reservation or get there when doors open for a seat. Pro tip: they have some of the best she-crab soup in the world. For an elevated dinner option, book a table at Vic’s on the River.
visitsavannah.com
