Real talk—I think I have more pictures of Charleston on my computer than I do of my entire college experience.
Okay, maybe not really—but it’s certainly close. And when a city is as colorful, bright, charming, and welcoming, it’s hard to not snap a picture on every street corner.
A couple of weekends ago, I went on a fun girls weekend to the Holy City with two of my college roommates and our good friend. We were in town for 48 hours and covered a lot of ground in that time. It was such a fun trip!
Since Charleston is a great option for a long—or regular!—weekend trip, I thought I’d share our itinerary since it’s a great way to hit all the high points without feeling rushed. If you’re looking for something a little more detailed, be sure to check out my Charleston Travel Guide, which is a repository of all my favorite spots to eat and dine in the city, as well as advice on where to stay! I updated it last weekend, so it includes recommendations from this trip, too.
We flew to Charleston on the first flight out of DC—we made it to CHS before I usually make it to my office. Our first stop was The Dewberry hotel, where we were staying for two nights. We shopped around quite a bit on Expedia before booking this trip, and ultimately, booked The Dewberry because they were running a great deal—round trip airfare and two nights for $535/each. We would have never been able to afford The Dewberry otherwise, so I’m really glad it worked out. The staff was so welcoming, and we dropped our bags off for them to hold while we went off to explore Charleston. The Dewberry is in the Historic District, so it was pretty much walking distance from everything we wanted to do—we only took an Uber to and from the airport.
About 45 minutes later, we met up on King Street for some shopping. While we popped into a few chain stores, we especially enjoyed checking out local boutiques. My friends introduced me to the upstairs patio at The Skinny Dip—as seen in the left photo above—which was the cutest, preppy store that carried KJP, Buckley K, and other all-American brands.
After relaxing for a bit on Skinny Dip’s patio, we walked down the street and stopped by one of my Charleston favorites—Moon & Lola. Of course, they have other stores, but nothing beats a King Street trip to see their cute pink couch and latest selection of jewelry. I picked up a few cute cards for graduations, birthdays, and weddings that I’m excited to give out.
We then popped into Candlefish. It was my first time going, and I am kicking myself for not going sooner! There were so many candles to choose from, and quite the selection of well-curated gifts and stationery. I picked up a candle to bring home—I opted for no. 12, which is a beautiful orange smell—and grabbed one for Monica, too!
Next door to Candlefish was the Savannah Bee Company. They had a wide variety of honey-made beauty products, but let’s be real, we were there for the food samples. They gave out apple slices for taste-testing—my favorites were the orange blossom honey and whipped honey, which is akin to butter, so no surprises there.
Because of all that shopping, we worked up an appetite. Luckily, we had a lunch reservation at Husk. This was the one concrete plan we had the entire trip, and it was so nice to just explore Charleston at our own pace without being beholden to a schedule. However, Husk is so popular that a reservation is pretty much needed no matter when you go. I always opt for lunch because it’s way less expensive than their dinner, and most of the same food.
We decided to be ladies who lunch and indulge in a bottle of wine and some house-made cocktails. We started with the cornbread and pimento cheese, both of which were delicious. For my main, I opted for their burger since they put bacon in the patties—it’s two thin ones on the house-made bread—and serve it up with a special house-made sauce.
We skipped dessert because we were stuffed and headed out for a nice long walk around Charleston.
First we walked over to the Pineapple Fountain in Waterfront Park, which during these warm summer months is a popular place for kids to wade. After a few minutes of soaking it all in and enjoying the breezes coming off the Cooper River, we walked by Rainbow Row on our way down to The Battery.
We took a leisurely stroll down the promenade on the Battery, taking in all the gorgeous mansions and eventually ending up in the park at the end of the peninsula where all the cannons from the former battery used to be. We sat in the middle of a gorgeous gazebo for half an hour or so to escape from the sun and just take it all in.
After we explored The Battery, we walked through the Charleston City Market and then back up to The Dewberry to check into our room. I loved taking pictures of all the antebellum homes and peaking into their gated yards. Though it was about a half an hour walk from The Battery to The Dewberry, we didn’t mind since the scenery was so pretty.
When we arrived back at the hotel, we checked into our gorgeous room and took some power naps—we had been up since 5 am! After our naps, we decided to grab drinks from The Dewberry hotel bar, The Living Room, to enjoy while we were getting ready. The bartenders at The Dewberry were amazing—so friendly and helpful, and we ordered many more grapefruit La Croix and vodka concoctions throughout the duration of our stay.
For dinner, we went to Fleet Landing. Y’all, this might be my new favorite place in Charleston because it’s right on the Cooper River!
The wait for a table was about an hour and a half, but we didn’t mind because the back bar was right on the water, meaning we had a great view of the sunset over the water. The pomegranate mojitos didn’t hurt either. It was seriously such a fun atmosphere and happy hour.
For dinner, I opted for a salad with their low country gumbo and it didn’t disappoint. We finished dinner off with a nightcap at—you guessed it—The Living Room before calling it a day. We had a long one!
We slept in a bit on Saturday before heading to Stars Grill & Restaurant to take advantage of their weekend brunch—$3 mimosas and a $25 all-you-can-eat breakfast buffet. I think we as a table may have consumed an entire quiche solo—it was just that good.
Once we stuffed ourselves silly, we took another stroll down King Street to pop into some favorite stores from the day before and explore new ones. We then popped down to Chalmers Street, which is one of five remaining cobblestone streets in the city, before heading to The Vendue Rooftop for a lazy afternoon drinking wine and talking about life.
After about three hours at The Vendue, we headed back to the hotel for a power nap before heading to dinner. We ate at the rooftop at Henry’s. While the food was decent, the service was terrible—it took us 20 minutes to get even the most basic request, so I’d recommend skipping this place and finding somewhere else.
However, we picked the restaurant since it was close to our ghost tour! I honestly don’t know the company we used—we were simply walking down North Market Street after the Charleston City Market and someone handed us a flyer with a discount. We knew we wanted to take a tour, so we were an easy sell. (If this is something you’re interested in doing, I’d recommend walking around the same area—lots of coupons floating around and you can compare tour times and lengths. We also considered booking online ahead of our trip, but waited to see what the weather was going to do.)
Our tour left from the Charleston City Market at 10 pm and lasted about 90 minutes. What I loved about our tour was that our guide also infused a lot of history into his commentary. My favorite part of the tour was when we discussed The Mills House—which is the pretty pink hotel I’m sure you’ve seen on Instagram before. (It’s the righthand photo below.)Tthe building dates back to before the before Civil War, surviving the Charleston fire of 1861, the war, an earthquake, multiple hurricanes, and eventually, abandonment. in 1970, the City rebuilt it—and added another floor! There’s also a ghost of a woman in an 1860s-era purple dress known to pass through the lobby between 11pm and 1am. Much to our dismay, we did not see her ;].
After our amazing ghost tour, we had one last nightcap at The Living Room at The Dewberry and then packed up to head home after a wonderful trip.
After covering a lot of ground, we flew out early Sunday morning. I seriously considered not getting on the plane! If you’re looking for the perfect girls’ weekend, I can’t recommend Charleston enough. And—we’re looking for our next destination, so if you have any favorite destinations for a long weekend, let me know! x