At the end of September, we finally made it to Charleston, meeting up with our friends, Shawn and Laura, who live in Greenville. We’ve been waiting to explore Charleston for years, so I took the itinerary pretty seriously. To my surprise, we followed it pretty closely and it ended up being an incredible trip.
The following itinerary is three days full of activities, food, (lots of) drinking and exploring all the areas surrounding Charleston. Disclaimer: We had a vehicle with us, so we did a lot of driving around to visit Folly Beach, Sullivan’s Island and Mt Pleasant. While you can explore Charleston in a few days, the other areas are just as beautiful and shouldn’t be missed, so rent a car if you can.
I’ve marked all of my absolute favorite, can’t-miss spots with an asterisk.
day one
Arrive in Charleston as early as you can manage. Fortunately, Chicago had flights heading to Charlotte as early as 5 am, so we were able to make the connection pretty quickly.
We chose an Airbnb near Spring and Coming, but if you’re looking to splurge on a hotel, I’d recommend 86 Cannon, which is a boutique hotel in a restored house and full of Charleston charm.
Drop off your bags, and head to Leon’s Oyster Shop* for lunch. Given that Charleston is extremely hot in the summer, even in late September, be sure to take advantage of their frozen drinks, like frosé and frozen gin & tonics (so good).
You’ll of course want to grab a few oysters (fresh and fried), but don’t forget the fried chicken; the chicken sandwich was the perfect welcoming meal.
After you’ve finished one (or two) frozen G&T’s, head down the street to High Wire Distilling Co. for a tasting or a cocktail at their industrial bar. They also do tours of the facilities if you’re interested and their curated section of goods and mixers almost tempted me to check a bag home.
Since we had woken up at 3 am, we were in desperate need of a pick me up, so the giant sign promoting the Iced Irish Coffee caught our attention immediately. I wish I had written down what was in it, because it was incredible.
Once you’re highly caffeinated or a little tipsy, head south, walking on King Street to check out all of the shops. For the candle-lover (or gift-giver) check out Candlefish*; for the fashion-lover, Hampden Clothing; but walk slowly as there are tons of boutiques and small businesses along the main road to step into.
If you’re traveling with a male (or two), they’ll most likely break off from the group to go grab a beer at a rooftop hotel. Join them! Head over to the Restoration Hotel, taking the elevator to their rooftop bar, which has amazing views of the city. The drinks aren’t half bad either; I recommend the Pastel Antebellum, a grapefruit, pomegranate and tequila cocktail to help with the unrelenting heat.
After a lot of walking and drinking, you’ll be ready for another meal. We opted for Minero on Bay Street, but passed tons of restaurants on the way that I had read rave reviews about. (Ed Note: Charleston can get pretty pricey really quick, so we opted for one nice dinner on night two and kept the others fairly reasonable.)
If you’re down for another drink, you have to check out The Gin Joint*, a small house-bar, with inventive cocktails and a “bartender’s choice” option with a list of adjectives; the prompt that you choose two and leave it to the bartender. I, of course, went with tart and smoky, and while I have no idea what was in my drink, it was perfect. Had we not been drinking all day, I could have stayed for hours, trying different combinations. The best part? Almost all of the cocktails were only $12. (Cheap compared to a lot of unique bars similar in Chicago.)
Head back to get a good night’s sleep, because you’re in for a busy day tomorrow.
day two
Walk to Callie’s Hot Little Biscuit and pick up breakfast provisions for the group (or yourself.) I recommend downloading the app and ordering ahead to skip the insane line you’ll most likely arrive to see. Don’t sleep on the spicy pimento cheese or the cinnamon spread, so order sweet and savory options to try it all. 
Make your way to Boone Hall Plantation & Gardens, a beautiful plantation known for its appearances in movies like the Notebook. When you arrive, be sure to sign up for a tour time (and ask if Ed is giving the tour, because he was incredibly engaging and makes the tour so fun.)
If you’re waiting for your tour, you can walk around the grounds, checking out the cotton gin, the slave quarters (which include a small tour as well) and the dock.
Don’t stay too long, as you’ll need to head back to Charleston for lunch at Xiao Bao Biscuit*, which is only open until 2 pm. I am not joking when I say this was my absolute favorite part of the trip. You CANNOT miss the Okonomiyaki, a crispy cabbage pancake. And don’t forget to add the farm egg, bacon AND pork candy (katsuobushi) on top as well. There were multiple times on the trip where I just wanted to go back and get this again, but held back.
On your way back from lunch, swing by Mac & Murphy, a popular stationary shop, and stock up on cards for all upcoming holidays, birthdays, celebrations, before gearing up for an afternoon bike ride.
There are lots of bike shops in Charleston, and while we settled for Affordabike (close to where we were staying), the Bicycle Shoppe was also recommended, just further downtown. Once you’ve picked up a bike (and helmet,) head to the Aiken Rhett House. You can do a tour, or just check it out from the outside as you make your way to Waterfront Park, where you’ll find the famous pineapple water fountain.
After heading south, you’ll start getting distracted by the insane, massive houses in the South of Broad neighborhood, known for the Rainbow Row. After looping around the south of Charleston, check out the White Point Gardens and Colonial Lake before heading to Millers All Day for an afternoon pick-me-up.
Return your bikes and head back to your hotel to freshen up for dinner.
Hopefully you’ve made your dinner reservation at Husk* (well in advance,) but if you haven’t, put your name in for a table and head next door to their cocktail lounge for small plates and drinks while you wait.
The menu changes almost every night, but we had the General Tso’s Octopus with Fried Rice, Cider Glazed Chicken with Pan Fried Chèvre Dumplins and the Confit Duck Leg with a Sweet Potato Pancake. Every menu item is excellently curated, with local ingredients and well worth the wait and price. We finished up with a Smores Empanada and quickly ordered an Uber to carry us home after indulging.
If you opted for a lighter meal (and didn’t also order three appetizers with your cocktails while waiting), grab a drink at The Ordinary on your way back to the hotel.
day three
After two activity-packed days, you’ll be happy to pack up the car with your beach chairs, towels and a good book and head to Sullivan’s Island for an afternoon. If you’re up early, grab a coffee at Vintage Coffee Café or Brown Fox Coffee Co. in Mt. Pleasant and weave through Old Village checking out the beautiful homes.
We lucked out with a semi-cloudy morning, so Sullivan’s Island wasn’t packed with beach-goers early in the morning. If you’ve got time, head to The Obstinate Daughter (or Poe’s Tavern) for brunch before grabbing your gear and heading to the beach. I highly recommend downing an entire breakfast pizza before sliding into your swimsuit, but that’s just a personal preference.
While you’re not supposed to have beverages on the beach in Sullivan’s Island, you could pick up some supplies at Middle Street Market, along the main stretch, and keep them hidden from the beach patrol; it’s a hefty fine if they catch you. Otherwise, settle in for a relaxing afternoon at the beach.
Once you’ve had enough, head back to the hotel to rest up before grabbing a pre-dinner beer at Revelry Brewing. If it’s nice out, head to the rooftop.
Next, you’ll head to a local establishment, known as The Wreck, to consume as much fried food as you can handle. You can also try everything grilled or boiled, but I love fried shrimp and oysters. The boiled peanuts are a local classic, that I had never heard of before, but they are so addicting. You’ll probably want to order an extra side of them.
Once you’re sufficiently stuffed, don’t forget to order the key lime pie and the banana pudding for dessert to push the limit; they’re both so worth it.
By this point, you’re probably dying for an early night, so head back to the hotel for your last night in Charleston.
day four
If you’re not tired of eating and drinking yourself into oblivion, you can head to Butcher & Bee for brunch before leaving town. If you want something lighter, grab a coffee and a scone at The Daily*.
On our way to the airport, we had a couple hours to spare, so we drove around looking at houses on Daniel Island—a beautiful area between Charleston and Mt Pleasant and started picking out houses to live in one day.