If you ask me, there’s no better place for a road trip than the South. We have so many great cities, all within a fairly small region, that are worth a visit for the food, culture, and beautiful architecture, not to mention the great weather year-round. If you need some guidance, I’ve got the top seven cities I think you should put on your travel bucket list but there are plenty more in addition to these! So, pack up your car with lots of snacks and a really good playlist because you’ll be on the road for awhile.
Perhaps my very favorite Southern city, Savannah has it all: historic architecture, great food, charming people, beautiful town squares, all that SCAD has to offer in terms of culture, and it’s on the water. When you visit, I recommend sticking to the center of town, away from the touristy shops on the river (unless of course, you’re taking an evening walk and getting gelato from Peaches & Cream). Explore the squares, the shopping on Broughton Street, and eat your weight in Southern food. A must see is The Paris Market and E. Shaver books, which I’ll talk about more in my upcoming Savannah recap.
As of right now, Charleston is definitely the most popular destination in the south and has been for a few years now thanks to its colorful architecture, thriving food scene, and proximity to the beach. If you’re going for the first time, may I recommend Julia’s Charleston Guide to help plan your itinerary? At the very least, I definitely recommend staying in a beautiful inn like Zero George or 86 Cannon, having dessert from Sugar Bakeshop, a biscuit from Callie’s, dinner and drinks at Chez Nous, a stop at the Gibbes Museum of Art, and a bike ride around town.
I’m a bit biased here because I live very close to Winter Park and am there all the time, but for good reason! It’s charming, elegant, and on the water with shopping, lots of good food and has made Southern Living’s best food towns many years in a row. I’ll have a full Winter Park travel guide up for you later this month for the next time you’re in the Orlando area, so I won’t spoil the details now but there are plenty of beautiful gardens, museums, and incredible restaurants for you to try when you’re here.
Atlanta has so much more to offer than just a layover at Hartsfield-Jackson. Spend the day at Ponce City Market enjoying the food hall and playing games on the roof, then go shopping for cute things at Mashburn, Cover Books, and Little Barn Apothecary. Check out the food market at Star Provisions then grab a green juice from Kale Me Crazy before capping the night with drinks at the Garden & Gun club.
Another (justified) bias here, as I lived in St. Augustine for several years while I was in school at Flagler College and absolutely adored it. This is a great place to explore on bicycle from the historic Castillo de San Marcos to all of the beautiful back streets in and around Flagler’s campus. Stop in at The Floridian for the best southern food, The Hyppo for their iconic popsicles, and The Kookaburra, either downtown or on the beach, for really good Australian coffee.
It might seemingly be the bachelorette party capital of the United States, but there’s more to Nashville than bridesmaids and country music. Have a classic southern lunch of collard greens, mac and cheese, and biscuits at the iconic Loveless Cafe then head into Draper James for a sweet tea and some cute new pieces for your wardrobe. Stock your personal library at Parnassus Books, owned by author Ann Patchett, pick up some pastries from Marché Artisan Foods, beautiful pieces for the home from White’s Mercantile, clean skincare from Lemon Laine, then finish off your trip with some live music at Bluebird Cafe.
If you want to be surrounded by endless food options as well as unique culture and gorgeous architecture, New Orleans is the city for you. Check out Horn’s for the vegan BLT, Herbsaint for small plates and a glass of wine, and Galatoire’s for classic New Orleans dishes. Stop by Willa Jean or Boulangerie for pastries and you can’t leave NOLA without having chicory coffee and beignets at Cafe du Monde. After all the meals, book a class at Romney Pilates then top off the trip by seeing the Preservation Hall Jazz Band if they’re in town.