A couple of years ago, we drove from NYC to Delray Beach, FL, and back. We’d been invited to spend New Year’s Eve with friends, and I thought it was the perfect opportunity to take a road trip on this route I’d never done. Matt was less enthused, but I convinced him that driving our own car meant we could actually stop at flea markets and antiques shops. On the way down we rode with our daughter Clara, her friend Grace and her mom, Christy, which meant we had to be pretty plotted out because we needed two rooms during peak holiday season. Since Matt was doing all of the driving, and because the point of driving and not flying was to actually stop and see things along the way, we tried to break it into four hours max of driving per day.
Our overnights were in Richmond, Charleston and St. Augustine. Highlights were the hunt for the best peanuts, the most amazing breakfast sandwich in Richmond, our stay at the Dewberry in Charleston (we kind of all didn’t want to go any further!), and the stop at South of the Border. Lowlights were St. Augustine (our hotel was terrible and expensive! No offense to all the great things/people there—it was just a challenge to discover it while on the road), the Kennedy Space Center (why does it have to be so expensive?—there should be a drive-by price if you only have 1 hour!).
On the way back, it was just Matt and me (the others flew home), and we drove a totally different route, which I’ll cover in another post. I’ve had a lot of requests to put this list together, as many of you make this drive over the holidays—and I hope you’ll add your favorites in the comments! Note: If I just list a place without details it’s because I didn’t stop there, but wish I had, because it came highly recommended. There are only so many meals you can eat and stops you can make in a day! Also, I’m adding in some other spots in South Carolina that we didn’t make on this trip, but just did last weekend (in the Hilton Head and Beaufort areas).
This list follows our route from north to south.
BALTIMORE
We left New York around 9am, planning to find the best crab cake here for lunch. Because there was no indoor dining at the time, several of the places that we wanted to stop at were shut, but we ended up doing a crab cake tailgate at Jimmy’s Famous Seafood and were very happy.
RICHMOND
I’ve only skimmed the surface here because each time I’ve been to Virginia’s capital it’s for an overnight (it’s about five hours from NYC), and each time I also say we’ll come back on a dedicated trip. Yes, it has a strong food scene and some good hotels, but this trip we also wanted to visit the Marcus-David Peters Circle.
STAY
The Quirk: We loved it—cute decor, warm staff, super dog friendly, with a good bar in the lobby, where we unwound at the end of the long drive.
The Jefferson: I stayed here on a previous road trip and liked the old-school vibe, but it was so much more than we wanted to spend this time—plus teenagers and the Quirk are much more sympatico.
FOOD + DRINK
Saison is where we had dinner. It was an easy walk from the hotel, and it was delicious.
Salt & Forge: We stopped here for breakfast and all got the chicken biscuit sandwich to-go—which was insanely good. Next time we’ll try an actual breakfast sandwich (just looking at their menu right now is making me want to hit the road!).
AND…
Marcus-David Peters Circle is a must. The area around the statue of Robert E. Lee, which protestors informally renamed for a local Black high-school teacher shot by a policeman in 2018, has become a community gathering spot.
Virginia Museum of Fine Arts if you’re not leaving first thing in the morning.
There happen to be two cool men’s shops in town—Ledbury and Shockoe Atelier—and both create their own lines. I like to go into these kinds of stores to get the download on what’s happening, and I always end up meeting interesting people.
ALONG THE WAY
We were headed to Charleston, but meandered a bit. At the first local peanut billboard sign, Matt decided we needed to do a taste test. The first stop was just off I-95 at R.M. Wilkinson’s gas station (still in Virginia), which didn’t have peanuts worth stopping for, but did have the most amazing homemade lunch options, like navy bean soup, bbq sandwiches, and bacon-wrapped hot dogs. In the pursuit of a better peanut, we followed another billboard for Aunt Ruby’s in Enfield, NC, which didn’t disappoint: a lovely town caught in time, and the peanuts were delicious. (You can order them online!) I wish I could tell you that we ate somewhere amazing for lunch, but all of our detours ended up nowhere interesting when we were hungry. Had I known about Rocky Mount Mills (a restored cotton mill that’s home to breweries and restaurants), we would have stopped there!
River & Twine: An IG follower sent me this suggestion—it’s a group of well-appointed tiny cottages just a walk from the restaurants at Rocky Mount Mills. They loved their stay there—and it seems like a great overnight option off of I-95.
Scott’s BBQ, Hemingway SC
Kudzu Bakery, Pawley’s Island
South of the Border: This kitschy pitstop on the North Carolina-South Carolina border was definitely a trip highlight (especially for the girls). Stop for the photo ops, buy a bumper sticker and maybe some fireworks if that’s your jam (it’s definitely Matt’s).
Palmetto Peddlers Antiques Mall, Florence: 38,000 square feet, one of the largest in the state, and right off the highway. I can’t tell you how disappointed I was that we were too late
CHARLESTON
It seems a shame to only stop for a night, but ending a day here means eating really well, and it’s worth it just to wake up to walk or run to the river, past all of the lovely historic homes. Favorites are below, but check out our extensive Black Book here in this link.
STAY
The Dewberry: Pulling in here after all day on the road was just heaven. Super chic lobby, well appointed and comfortable rooms, and a rooftop bar where we met up with friends.
Post House: A great place to stay with an amazing restaurant, owned by the sweetest couple, Kate and Ben.
FOOD + DRINK
Leon’s: Fried chicken and oysters—exactly what we wanted at the end of the long day
Melfi’s: We ate here on a different trip—a little fancier, with great pizzas, steak and cocktails.
Lewis Barbecue: Epic barbecue with lots of tables both outside and inside
SHOP
King Street is filled with the usual suspect high-end stores, but there are a few independent ones that we really like: Grady Ervin & Co (a classic menswear store owned by Chip, the nicest guy, who makes a point of finding small designers, many of them local) and Worthwhile: The staff is a little preoccupied/chilly, but it’s refreshing to see brands like Astier de Villatte and Maison Louis Marie.
Indigo & Cotton is another men’s store (not sure why there are so many strong men’s stores on this road trip!) that has a great edit, including progressive Japanese workwear-style clothing.
Sightsee Shop is a travel-inspired retail store that also makes great coffee.
The Hidden Countship, owned by an Italian couple who grew up in Central Italy, came to Charleston on their travels, and never left, has beautiful Italian jewelry and linens.
AND…
Continue down King Street to the water and look at all the beautiful homes, then return on Meeting Street.
The International African American Museum is set to open in early 2022. Check this site for updates on the opening.
ALONG THE WAY
Definitely take 17 south out of Charleston and skip the I-95. It’s so much prettier, and if you can, detour to Beaufort.
Farm House Antiques is on 17 and we found some great vintage books there.
Carolina Cider Company & Clockwise Coffee wins for being the cutest roadside stand I’ve ever seen. Local products, delicious treats and a great coffee.
BEAUFORT
About an hour and a half below Charleston and an hour above Savannah, this coastal town is, for me, worth the slight detour. It’s all about the historic district (a national historic landmark), with Spanish moss draping the oak-lined streets and beautifully preserved homes, and the main street, which has no recognizable brand names on the storefronts!
FOOD + DRINK
Lowcountry Produce Market & Cafe: Great cafe with the most epic selection of pickled everything
The Fillin’ Station: Down and dirty bar that has good food. You’d really just come here if you were spending the night in town.
STAY
AND…
Bachelor Hill Antiques: Clever edit—we picked up a 19th-century bar there.
McIntosh Book Shoppe has a great selection of used books, all very well priced.
The Big Chill House (that was featured in the movie) at 1 Laurens St.
HILTON HEAD ISLAND
I wouldn’t go out of my way to come here—you know I’m a fan of the small, family-owned, historic…etc. But since I was just there (there’s an epic car show here once a year, which Matt loves), and many of you may have reasons to visit, I’m adding in my favorites. Also, a beautiful beach!
STAY
The Westin Hilton Head: I’m not so much recommending this as I am listing it—we did stay here, and it is on the best beach.
Sea Pines: We didn’t stay here because the car show was next to the Westin, but it looks more up my street.
EAT + DRINK
Nectar Farm Kitchen: We had the best breakfast sandwich here—fried bologna with an egg on it! Big emphasis on locally sourced product here.
Hudson’s Seafood House: We ate lunch here two days in a row! The freshest fish! Don’t miss the crab cake, the peel-n-eat shrimp, and the she-crab soup.
Chez Georges: Weird location in a sort of apartment complex that has several restaurants on the ground floor, but it’s a really good French restaurant! We had mussels/fries and a frisée lardon salad, and all the food on our neighboring tables looked fantastic.
Al’s Aloha Kitchen for green juices and acai bowls
Hinoki for great sushi
The Black Marlin Bayside Grill
Sea Pines Beach Club for a drink with a beautiful view
BEACH
Walk straight out of the hotel to the beach but go left—there’s a beautiful path and our friend who grew up there, the jewelry designer Selina King, says it’s one of her favorite beach walks.
Native Son Adventures for a boat tour to find artifacts and megalodon shark teeth
BLUFFTON AREA
Bluffton is roughly a half hour from Hilton Head, and we spent a night here before the car show. Nearby is Palmetto Bluff, a planned community that has residences, a hotel, shopping areas, golf course…the Lowcountry landscape there is beautiful.
STAY
Montage Palmetto Bluff: I’d only recommend this if you have more than one night, as the charm of it is getting to ride bikes around and take a boat out. The rooms are comfortable, and the restaurant is good, but it’s definitely on the splurgy side. Their wine list is impressive—small vintners from California and France, and some very recognizable—but I couldn’t get over how marked up the prices were.
Old Town Bluffton Inn: Right in the middle of the charming town of Bluffton, we didn’t stay here, but it looks promising.
EAT + DRINK
Farm Bluffton is the spot that every person recommended to us.
Cahill’s Market and Chicken Kitchen: A family-owned local favorite—come here for breakfast or lunch, and get the fried chicken.
SAVANNAH
We literally blew through this historic city and just stopped for coffee at the Paris Market. A proper list is coming soon, courtesy of the brilliant Rebecca Gardner.
JACKSONVILLE/ST. AUGUSTINE AREA
Right about here is where the race was on—we had to get to our destination. It was also the one place I didn’t have our hotel sorted before we left (big mistake—yes, I make them!). We had to find a place to stay that was between Charleston and Delray, and we wanted to have a nice town to explore, and I was stumped between Ponte Vedra and St. Augustine. So many places were booked up, so I ended up on the phone with Amex Travel to help secure a booking, and she highly recommended St. Augustine. What a disaster! The hotel, Casa Monica, looked great on the website, but was just awful—maybe because we overpaid ($500 per room!!) and it seemed like it should have been a fraction of that. Also, it just seemed a little bit dirty. The town was packed, and of course we didn’t make a dinner reservation (yes, another big mistake!), so I was sweating it. We ended up eating at the Floridian, which was excellent, and somehow had several open tables, so we were able to walk right in.
If I had planned ahead…these are the places I would have looked at booking instead:
STAY
Elizabeth Pointe Amelia Island
EAT + DRINK
Ice Plant Bar, St. Augustine
Singleton’s Seafood Shack, Atlantic Beach
The Bearded Pig, Jacksonville
Palm Valley Fish Camp, Ponte Vedra: not a down and dirty spot, but carefully sourced seafood.
Odd Birds Cocktail Lounge & Kitchen, St. Augustine
Smokin’ D’s BBQ, St. Augustine
The Burger Place, Melbourne, was highly recommended as a great burger spot owned by a French couple.
Our return route home to NYC via Thomasville, GA, Highlands, NC, Asheville, NC, and Charlottesville, VA, will be posted in early January!