They say New York is an assault on your senses. If that’s true, than Charleston is a love letter to them. The first time we passed through Charleston for a night about 5 years ago, we instantly knew we wanted to return and spend more time there. With 4 days to explore this time we really dove in and covered a lot of ground. Here – the best of what we discovered.
WHERE TO STAY:
The first time we visited we stayed all the way downtown near the Battery. While it was pretty, it left much of the rest of the city feeling a bit far away. This time, we made the Andrew Pinckney Inn our home base and I can’t say enough good things. Located just a couple of minutes walk from the City Market, it allowed for easy walking to both the historic Battery area and also further up King Street to some of our top pick eateries (more on this below). Plus, it was closer to the bridge over to Mount Pleasant for when we picked up rides to Sullivan’s Island.
And the Inn itself was exactly what you’d want in a charming Charleston accommodation. We stayed in a 2-floor suite which felt so luxurious (I wanted to take that mustard yellow couch home with me), but every room would have the same cloud of a bed we slept in and window views to watch horse drawn carriages click by every morning and palm trees sway. Plus, they have a rooftop dining deck where complimentary breakfast is served in the mornings and complimentary happy hour in the late afternoon. We ended up taking advantage of the breakfast almost every morning as a nice light option (build your own granola parfaits for the win) before indulging in some of the city’s heavier fare throughout the day.
If you have any other questions about our stay at the Andrew Pinckney Inn – I’m happy to answer!
PLACES TO SEE:
Nicknamed the Holy City, there are countless steeples that dot the city’s skyline, but it’s the beautiful historic homes that really drew us to Charleston. If you’re looking for Instagram-gold, start at Rainbow Row (a stretch of pastel hued homes) and walk south and west through the back streets and hidden alleys like Longitude Lane and Stolls Alley (where we shot these photos). You’re going to want to make some space on your camera roll.
Next continue up King Street for the city’s main stretch of shopping. While you’ve got big name designer and typical mall stores, they’re housed in pretty old buildings that make window shopping all the more fun. Plus, once you’re further up King Street you’ll see smaller, local businesses too. I loved Blue Bicycle Bookstore in particular.
And if you’re looking to see Charleston from a whole new angle – head to the Vendue Inn Rooftop. With two levels and nearly 360 degree views of the city, you’re going to want to get there about an hour before sunset to grab a good seat.. and then enjoy the show. It’s called low country for a reason – meaning there’s no mountains or hills to interrupt a seemingly endless view over the city, water and sky. The staff told me they do firework viewing at the Fourth of July and are planning a Solar Eclipse viewing this summer too. If you’re in town – those would be amazing! We ended up staying long after sunset due to the delicious drinks and great service. Adam tried local craft beers while I had the spicy tequila and fruit-infused ‘Takes 2 to Mango’.
DAY TRIPS BEYOND DOWNTOWN:
Since we had more time this visit we knew we wanted to get out of the main downtown area and explore greater Charleston. First on our list was a visit to one of the several historic plantations nearby. We chose Middleton Place but also heard good things about Boone Hall too – where the Notebook was filmed and Blake Lively & Ryan Reynolds got married! Locals assured us all of them are beautiful and rich with history. This would be a great stop if you’re traveling with a family as well since there’s lots to learn and plenty of room to run. While we could have spent all day wandering Middleton Place, at the minimum you’re going to want to allot 2-3 hours plus 30 minutes for driving each way. This particular plantation sits right along the Ashley River (we saw more than one alligator lurking in the water) and has all of the Spanish moss, old grand buildings and manicured gardens you’d want in a southern estate.
Our second day trip out of downtown was to Sullivans Island – located across the famous Arthur Ravenel Jr. Bridge on the Mount Pleasant side of town. There are a few beaches just outside of Charleston (Folly’s Beach, Kiawah Island), but we chose Sullivans for its proximity to downtown (about a 25 minute drive) and because it felt uncrowded while still offering a few close-by food options that we could walk to. We liked it there so much that we ended up going back a 2nd time for a few more hours.
And now… the good part. The food. Charleston has some of the best food options in the country in my opinion and they aren’t all the heavy Southern-style you may expect. For starters, one of our very best meals was at The Obstinate Daughter on Sullivans Island. Adam had gnocchi (the best in his life!) and I had a lemon, shrimp & pesto pizza that was a total knock-out. Both of us tried local craft beers that were great too. And the decor here is just spot on – nautical meets modern. It’s exactly how I want to decorate the lake house.
Two of our other favorite lunch/dinner spots were the tiny 167 Raw near our Inn (be prepared to wait in line, but it’s worth it) where I got a lobster roll and rosé and Adam went with an Oyster Po’Boy – both stand-outs. And you can’t miss Darling Oyster Bar further uptown on King Street (we naturally got oysters – plus an entree.. and side of hush puppies.. because Charleston). Whether you sit along the front oyster bar or in the main dining room the place is beautiful and just a fun scene.
If you’re looking to indulge your sweet tooth – you’ve got to head up past Darling Oyster Bar to Sugar Bakeshop. Tucked away on a little residential side street we came here the first day for birthday cupcakes and weren’t disappointed. And along King Street, you’ll want to cool down with a trip to Jeni’s Splendid Ice Creams. I loved that you could get a trio of mini scoops with a waffle cone wedge stuck into the bowl to avoid the inevitable cone drips in Charleston’s heat (salted peanut butter and lemon blueberry were our favorite flavors).
If you’re looking for a quick breakfast – try Callie’s Hot Little Biscuit. In this couldn’t be cuter, miniature spot you’re going to find some of the best Southern biscuits of your life. Adam got a full breakfast sandwich but I just got the trio of mini biscuits – with homemade brambleberry jam and cinnamon butter on the side. If it hadn’t been our last day there we would have gone back.
And lastly – if you’re on your way further uptown (we stopped here on our way back from Middleton Place), Leon’s Oyster Shop wins for not only awesome food but a really fun atmosphere. We ate outside of this renovated garage meets restaurant on their colorful patio furniture where I sipped frosé (frozen rosé.. enough said) and had lunch. The menu was simple but made with unexpected flavors and fresh ingredients – case in point: Adam’s fish sandwich came with a seemingly nondescript cucumber salad. It ended up being so insanely good that I asked our server for the recipe. My only regret is not having time to hang out there longer.
Charleston has tons to offer, but what we love most is the beautiful historic homes, the great food, the slower pace and the sweet people. Rent bikes to see the town easily and try to spend at least 2 nights so that you can really get a feel for the place. We’ll definitely be back. Have more questions? Shoot me an email or find me on Instagram.
And a special thank you to the Andrew Pinckney Inn for hosting us and the Vendue Rooftop for having us. As always, all opinions are my own.