We lived in Charleston from 2003 to mid-2006 and I loved it. I’ve only been back to visit once since we left, but I spend a large portion of my time reminiscing over things I used to eat there. If you’re going to Charleston, I suggest packing some very stretchy pants for your return journey as you will likely gain an extra ten pounds. Here are a few things to do:
Places to Eat
My favorite restaurant in Charleston is FIG; if you only go out for dinner once, I’d make it here. The food is fresh, simple, and extraordinarily delicious, and they try as often as possible only to use ingredients from local growers. It's great just for drinks too -- they have a really nice bar and good drinks (jazz on Tuesdays too, I think.)
For a slightly upmarket lunch, SNOB (Slightly North of Broad) is a good bet -- full of ladies who lunch with their collars turned up and be-suited men doing business deals; they serve dinner as well, and both are equally enjoyable. It's downtown and very charming.
If you’re looking for brunch, suck up the wait and eat at The Hominy Grill – it used to be an old barber shop and it has a great atmosphere. If you want a drink out on the water, Fleet Landing is a great spot and has really pretty views at sunset. You'll find a lot going on food-wise on King Street; start with Chai's, a loungey-type of tapas joint. The food is a mixture of Asian and Spanish, which is far more delicious than it sounds.
Away from downtown, my favorite lunch spot is The Square Onion in Mount Pleasant -- the neighborhood looks like Disneyland, but they have the most AMAZING sandwiches: I still have dreams about the Sassafrass (and the Goose is really good too.) If you’re at the beach, Poe’s on Sullivan’s Island has great burgers and you can work it all off by strolling along the sand dunes afterwards. My second favorite restaurant is out in the Avondale district of West Ashley; it’s a little Italian trattoria called Al Di La and the food is incredible.
Places to Shop
If you like cooking stores check out Charleston Cooks on East Bay Street (right next door to SNOB, actually); it’s cheaper than Williams-Sonoma but with the same aesthetic. You could spend a few hours walking up and down King Street, the main drag; you didn’t come to Charleston to shop at the Gap, certainly, but you’ll find a lot of fun little local boutiques too; I like Worthwhile, Luna, and Stella Nova (kind of a mini Sephora).
Avondale is a haven of cute and quirky little boutiques, and halfway between Mount Pleasant and Sullivan’s Island you’ll find Linda Page’s Thieves Market, the world’s best vintage furniture store; you probably won’t be able to drag anything home with you but it’s fun to browse.
Other things to do
Stroll along the Battery and look at all the beautiful houses, then walk down to Rainbow Row, through all the cobblestone streets (Church Street is especially pretty), and down to Waterfront Park where kids splash in the huge pineapple fountain in the summer and you can sit on a porch swing looking out over the water.
You can take a lot of great walking tours; I recommend the Dark Side of Charleston, and also the nighttime of the Old City Jail. Charleston is at its most charming when you just walk around, discovering its hidden nooks and crannies. If you like little churches, the French Huguenot Church is super charming, and you’ll feel like a local if you walk around Colonial Lake at sunset. Most guidebooks will also tell you to go to The Market; you should do it—mostly to say you’ve done it and because it’s so Charleston—but know that it’s the Times Square of Charleston, so you’re more likely to run into tourists than natives.
Every Saturday, there’s a great little Farmers’ Market in Marion Square Park (fun fact: we used to live right opposite here on Charlotte Street!) You can go for breakfast and eat your crepes in the park in the sunshine, or stock up on supplies and then head out to the beach (Sullivan’s, Folly, or Isle of Palms) for a picnic. Four times a year, the city hosts the French Quarter Art Walk downtown, which is super fun (and free!); you walk from art gallery to art gallery and there’s wine and snacks in each. I took my mother on this in 2005 and she still talks about how much fun it was.
For still more culture, I’d also recommend a visit to the Gibbes Museum of Art, which is manageable enough that you don’t get exhausted halfway through. You might also want to check out a performance by the Have-Nots, Charleston’s local comedy troupe, who are hilarious. You’ll often find cultural events going on at the College of Charleston too; it’s a pretty campus to stroll through, if nothing else.
For out of town excursions, visit one of the plantations about a half hour outside of town; I like Drayton Hall best, though Middleton Place and Magnolia Plantation & Gardens are also both very interesting. Also take a ride out to the amazing Angel Oak and bring your camera (you’ll see why when you get there.)
Things to remember
From about March to September, Charleston is hot, hot, hot—and super humid and muggy too. My favorite months there are October and November, when the skies are blue but the temperature has fallen enough to be comfortable.
One of my favorite things about living in Charleston was that everyone always dresses up: it gives you a good excuse to put on a pretty dress and a pair of heels when you go out for dinner. If you are a man and you have been dying to wear seersucker, now is the time and the place to do it.
Beware of palmetto bugs! These are basically flying cockroaches---though calling them palmetto bugs makes them so much less horrifying—and the first time you see one, you will probably crap your pants.