My extended family has gone to Kiawah Island for decades. While my first trip there was just a few years ago, I grew to love it pretty quickly. This is that "annual vacation" kind of place where people return year after year. The beach has ten miles of hard-packed sand, so you can ride bikes. Really, there is a sense of relief like most beach destinations. It's also big for golfers (not my thing). Here's an article I wrote for National Geographic: Into the Wild on Kiawah Island.
I LOVE staying at The Sanctuary on Kiawah Island, a grande dame southern resort with an amazing spa. Every single night, we go to The Ocean Course clubhouse for drinks at sunset (and save one night for dinner at The Atlantic Room). You can also rent a condo or a house - if you're traveling with a large family, a house is the way to go. Just make sure to rent a bike before you get there, especially if it's summer high season - the bike trails are flat, shaded, and so lovely!
Before you enter Kiawah Resort (it's a private island so you have to go through security - but if you want to day trip from Charleston, just book a restaurant reservation somewhere on the island and you can explore), you'll pass Freshfields Village, which has cute clothes shops and what used to be a fantastic grocery store called Newton Farms. Now it is called The Village Market and it is terrible - a complete chaotic mess, run by Harris Teeter. I’m holding out hope it will return to the way it used to be.
As much as I enjoy Charleston, I am always eager to get back to Kiawah. Favorite restaurants: The Fat Hen (stop on your way to or from Charleston) is the best restaurant in the area - love it for brunch or dinner; Hege's in Freshfields Village for French-inspired food; The Ocean Course clubhouse for crispy shrimp, French fries, and wine. The best food you can find in Kiawah is by cooking in your rental house!
Husk: Still the most talked about restaurant in Charleston, chef Sean Brock gets tons of press and it’s definitely worth a visit to see what all the fuss is about. It's Southern food gone completely bold and sometimes unconventional (like buffalo pig ear lettuce wraps - not my thing!). Innovative cocktail list and a menu that changes daily.
McCrady’s: I love McCrady's, also helmed by chef Sean Brock. Housed in a Georgian home where George Washington once had dinner, McCrady’s is old-school and delicious.
Bull Street Gourmet: On King Street in downtown Charleston. BEST sandwiches, like tomato and mozzarella and chicken salad. Their granola bar is also great, filled with oats, brown sugar, cranberries, gold raisins, almonds, walnuts, cinnamon and honey. Ideally, I stop here to pick up food for the plane on the way home - or if you need a break from eating and want something super casual.
Schooner Pride: If you feel like a sunset sail, this company is great.
Palmetto Carriage Tour: One of those touristy things to do in Charleston - but it's fun to see all the gorgeous homes by carriage.
Middleton Place Plantation: No relation to Kate, but this Middleton family is equally storied (they can count 1,600 descendants) The gardens here rival the best in England and were laid out in 1741. The number of original objects on display is staggering. You can stay on-site at The Inn at Middleton Place, which is modern and minimalist. This is such a beautiful place.
Gibbes Museum of Art: Your (art) culture stop in Charleston. Check out which rotating special exhibits are on display and don’t miss the permanent “Charleston Story,” detailing the city’s rich history.
Charleston Place: I have now stayed here a few times and I don't LOVE it. It’s deceptively large, with 441 rooms, which means convention and meetings often take over. The location is perfect and I do love the classic Thoroughbred Club for afternoon tea and cocktails, and the fact that you can score a mini Charleston Chew when you go talk to the concierge.
The Peninsula Grill: Please do not leave Charleston without sampling a slice of their famous twelve-layer coconut cake. I marched into the bar, ordered one to go, and ate it in my room. Well, some of it. It’s really rich!! This is also one of Charleston’s nicest places to have dinner.
SKIP! Boone Hall Plantation: Boone Hall gets a lot of attention because of the famous “Avenue of the Oaks.” But after Middleton Place, Boone Hall feels contrived. Almost all of it is a reproduction and there was not a single ounce of Southern friendliness to be found when I visited.