Editor’s Note — if you’re looking for additional Charleston recommendations, here are some other posts to check out:
- Charleston Travel Guide
- What to Do on a Girls’ Weekend in Charleston
- What to Do on a Solo Trip to Charleston
- A Long Weekend in Charleston
So let me just preface this post by saying, I was not supposed to be in Charleston for New Year’s Eve. Long story short, those plans fell through because of the pandemic—and since my one of best friends and favorite travel partner, Emma, was supposed to come along for said plans, when they fell through, we immediately started working on our Plan B. Given the holiday, we were priced out of a lot of options, but when we could both find flights for around $300 from our respective cities to Charleston, it was a no brainer. Charleston is one of my all-time favorite places, and no matter how many times I’ve been, I’ll never complain about the opportunity to go back—plus, there’s enough in the Holy City to explore that I never feel like I’m taking the same trip twice. I would absolutely love to live there one day—there is nothing quite like the Lowcountry life.
Getting out of town for this trip was just what the doctor ordered. As I’ve mentioned, at the end of last year, I was at the end of my rope. So many things about this trip just felt like divine intervention. I know this trip was meant to be, and so many things about it just unfolded perfectly—I know God was looking out for me. I truly don’t think I’ve ever been on such a restorative trip. Between the amazing weather—I was able to wear sandals on January 1, the amazing food and drink, and the amazing charm of Charleston, it was just so much FUN.
We flew into town on Wednesday morning and I stayed until Saturday evening—it was the perfect amount of time and let’s just say, quite the reality check to land back in DC to snow two days later. I’m excited to recap this amazing trip below as we did so many new-to-me things that I am excited to share with you today!
WEDNESDAY AFTERNOON —
Emma and I started our days bright and early on Wednesday morning—her flying into Charleston from NYC and me from DC. We timed our flights to land around 10:30am so we could meet up at the airport and share an Uber into town. (The airport is a quick 15-20 minute drive, and getting an Uber there is really easy.)
Despite it being a Charleston institution, we had never been to Leon’s Oyster Shop before—so took our Uber directly from the airport to Leon’s for lunch. They open at 11am and don’t take reservations, so getting there basically when it opened meant we didn’t have to wait at all. (Though if for some reason, you do find yourself facing a wait at Leon’s, I think it’s worth it and they have a section of the bar where you can order drinks while you wait!) We grabbed two seats at the bar and it was such a fun atmosphere—and they still had all their Christmas decorations up, so that was really fun, too. We split the hush puppies to start and then both did fried chicken sandwiches. I splurged and also ordered the scalloped potatoes, which were so good and indulgent. Everything we ate was delicious!
After, we walked a block or so down to The Daily for iced coffee, and from there, took an Uber over to Mount Pleasant. When we began searching for hotels for this trip, there were plenty of options available, but because of the holiday, most hotels in downtown Charleston were going to run us between $400-500 a night. That wasn’t really in the budget, so we decided to book at the Courtyard in Mount Pleasant, about a 15-minute drive from downtown—and even over the holiday weekend, it was only running $128/night. The hotel itself was adorable—it had palm trees lining the front, a gorgeous lobby, and really clean, spacious rooms. It wasn’t really walkable to anything, but we knew that going in, and it was relatively easy to get an Uber—we just had to bake in a 10-15 minute wait. Plus, staying on the opposite side of the bridge gave us the opportunity to explore a new-to-us neighborhood, and I am so glad we did!
Once we dropped our bags off at the hotel—and changed into clothing that was a little more appropriate for the 70+ degree temperatures, we took an Uber over to Pitt Street Bridge. Originally a bridge that connected Mount Pleasant to Sullivan’s Island, it’s now a pedestrian park that is absolutely stunning. The first part of the park is a paved walking path next to luscious green grass, with palm trees lining the whole way. When that ends, you walk onto a wood pier. Along the whole way, there are plenty of spots to fish and in the more shallow waters, you could easily get off the bridge and look for crabs. In the distance, you can see downtown Charleston and the Ravenel Bridge. It is just such a stunning place, and if I lived nearby, I’d find an excuse to walk around in this park often!
Once we were done enjoying Pitt Street Bridge, we walked around the Old Village District in Mount Pleasant. This is truly my dream neighborhood—the streets are filled with beautiful residential homes that don’t feel cookie cutter at all, each one prettier than the last. At one end of the neighborhood is Pitt Street Bridge and at the other end is the Shem Creek waterfront. In the middle of the neighborhood is a small commercial zone, with a few really cute stores—we loved Out of Hand, they had so much cute stuff and all their holiday decor on sale!—and The Post House Inn. When you walk off Pitt Street Bridge, you’re on Pitt Street, which runs the whole way to Shem Creek. We basically stayed on that street the entire time because it was so picturesque, but we did walk down some side streets if a house or the water caught our eye.
After we explored Old Village, we walked down to the Shem Creek waterfront area, which was THE BEST way to spend an afternoon. We got to sit outside by the water and enjoy a drink on a 70-degree December day. There are a ton of bars and restaurants all right next to each other lining Shem Creek, and a pedestrian boardwalk that connects them. There is also Shem Creek Park, which has a beautiful walkway with amazing views of the Harbor, Lowcountry, and all the boats coming in and out of Shem Creek. And, I would love to stay at the Shem Creek Inn one day!
We started our afternoon on Shem Creek off at Saltwater Cowboys, which was definitely my favorite. They had a huge outdoor deck right on the water, with multiple bars and a great playlist. We were able to snag a great seat with views of the shrimp boats and the sunset. If you only have time to go to one bar on Shem Creek, I’d make it this one! We split the fried pickles as a snack, but it looked like they had great bar food, too, if you’re looking for a full meal. We then grabbed a drink at Muddy’s Dock Bar after exploring the pedestrian boardwalk during sunset—they had a gorgeous outdoor space with incredible views of Shem Creek Park and the water. Some other Shem Creek bars + restaurants that were recommended to us that we didn’t make it to—Red’s Ice House, Tavern & Table, The Mill Street Tavern (they have a happy hour every day from 4-6pm!), and Water’s Edge.
WEDNESDAY EVENING —
After our afternoon happy hour on Shem Creek, we went back to the hotel to freshen up before a late dinner reservation at The Post House Inn. If you love to follow influencers like I do, you know there are a ton that live in Charleston and Mount Pleasant, and one restaurant they all frequent is Post House. Emma and I were really excited to check this one out. While they have a beautiful bar, that did seem to turn over quickly, I highly recommend reservations if you want to ensure you can eat here. It’s a popular spot and on the smaller side! We sat in the bar room and loved the ambiance. (They also have matchbooks at the host stand, if you collect like I do!)
This was our big splurge meal of the trip, so we made it a three course event—we started with the Caesar salad and the stone crab Carolina gold rice. For entrees, I did a steak special and Emma did the pork. And then for dessert, we did the buttermilk pie topped with blueberries. They also had an option on the menu to buy the kitchen a beer, so we bought them two—we thought it could be a great way to bring ourselves karma in the new year. I treated myself to some bubbly, and I loved that they served it in champagne coupes. The service was excellent and we shut the place down. I would love to go back for brunch!
THURSDAY AFTERNOON —
Since we both had caught really early morning Wednesday flights and our night ended up being on the later side, we slept in on Thursday morning and made it a pretty lazy one—which is always a nice treat on vacation. We kicked our day off with at 12:30pm lunch at 82 Queen. Located right next to Husk and Poogan’s Porch, I had somehow never been—and I can see now that was a huge misstep on my part. This was one of the best meals I’ve ever had in Charleston, and might have been my favorite meal of the whole trip. We ate outside on their darling pink patio and the food was great. We split a crab cake and tomato pie to start, and then both did grilled chicken salads. The food, the service, the ambiance, it was just all so top notch! I will definitely make sure I get back here next time I am in town.
After our amazing meal, we popped down to 151 Queen—a classic Charlestonian home with the cutest Christmas decor! I found it on Instagram and knew I wanted to walk by, so I appreciated Emma indulging me. After that, we spent the afternoon working our way up King Street from Queen Street, popping into any and all stores that caught our eyes. I was especially excited to pop into Madison Matthews as they have the most beautiful dresses. I tried on one so that when I place an order online, I knew what sizing I should do—and I ended up falling in love with the pattern, so I bought it! (It was one of their Folly Midi Length dresses—the pattern is being discontinued so it’s not online, otherwise, I’d show you what I walked away with.) If you’re looking for a beautiful, high-quality sundress for Easter or a spring trip, definitely check them out.
When we were about halfway up King Street, we noticed there were huge black clouds rolling into town. A quick glance on the weather app showed that it was about to start storming, big time. We didn’t have umbrellas and didn’t want to get wet, so we made a run for the Hotel Bennett and made it just in the nick of time. When we walked into their beautiful lobby, it was 3:50pm, and we realized Camellias, the champagne bar inside the hotel we wanted to check out, opened at 4pm. It was perfect timing for the rain to roll through! We were one of the first patrons inside Camellias when it opened and we decided to split a bottle of brut rosé. I love bubbly right now, so I was in heaven at Camellias—the decor was so cute. I can’t think of a better place to ride out a rainstorm!
THURSDAY EVENING —
Once we finished our bottle at Camellias, it was still raining and we had some time to kill before our dinner reservation. So we ran across a rainy Francis Marion Square to one of our favorite hotel bars in town, The Living Room at The Dewberry. (You can read about the time I stayed at The Dewberry here!) Walking into The Dewberry is like walking onto the set of Mad Men—I love the 60s decor, and they even stuck to the theme with their Christmas tree, as it was decked out in all the tinsel. Sometimes when I go to The Living Room, you can just grab a seat wherever, but since it was a busy night, they were seating people. We had to wait about 15 minutes, but got super lucky as we scored the chairs closest to the Christmas tree. The Dewberry smells amazing—and we both bought one of their signature candles, which they have burning everywhere. (They also have matchbooks, just ask the front desk reception!)
For dinner, we did dinner at The Grocery. The food was amazing, but I felt like the ambiance was a little lackluster—it just felt cold almost? We split a bunch of different things—the broccoli, served on top of whipped ricotta, along with the fresh bread, were my two favorite things. The sweet potato + ricotta gnocchi and bolognese bianco were also great!
FRIDAY MORNING + AFTERNOON —
Friday was NYE and to kick off the last day of the year, we started with the most important meal of the day at Big Bad Breakfast. We first discovered Big Bad Breakfast in Oxford, Mississippi and when we realized there was one in Charleston, it was absolutely a no-brainer. My last breakfast of the year was more like a lunch though, as I went for the BLT with avocado and a mimosa with fresh squeezed orange juice.
After brunch, we walked down King Street. It worked out perfectly, because the day prior we had explored King Street from Queen Street to the Hotel Bennett, so everything south of the Hotel Bennett. On this day, we were coming from north of the Hotel Bennett, so we were able to basically hit every store we wanted to on King Street. I just had to pop into Sewing Down South—fellow Southern Charm fans will understand, and we also loved Amanda Lindroth, Old Whaling Company, and Beckett Boutique. After our King Street rendezvous, we went to the Historic Charleston City Market. It is very touristy and usually quite crowded, but I’ve found great, affordable art there over the years and on this trip, I wanted ‘CHS’ hat—shown in a photo below—and knew they sold them at the market. (They’re at the Charleston Hat Man booth, if you’re also looking for one.)
From there, we just took a long walk around Charleston—walking by Rainbow Row, going down to the Battery, and walking around the French Quarter. I’ll never complain about a long walk around Charleston. I love looking at all the beautiful, colorful homes, and nothing beats a walk near the water.
We then went over to The Spa at Charleston Place to treat ourselves as we closed out 2021. We both got massages, and they were heavenly! We went over a little early so we could enjoy the facilities—we did the sauna and sat out on the pool deck because it was so warm. (The pool at the spa is also the hotel pool, so there were lots of kids splashing around and we didn’t want to get our hair wet, hah!) I almost never treat myself to a massage, so it felt really indulgent and was just what I needed.
Following our massages, since we had a late dinner on the books, we decided to get a snack at 167 Sushi. It’s housed in the original location of 167 Raw, right on East Bay Street across from the Harris Teeter. We split the fried chicken bao buns and the shrimp fried rice—it was a great way to cap off our fun afternoon.
FRIDAY EVENING —
We then went back to the hotel to catch some of the CFP Semifinal Games and get ready for dinner. We had a late reservation at Little Jack’s Tavern, which is our favorite spot for burgers in town! It has the best Americana decor, and their salads are also really good if burgers aren’t your thing. After we finished our meal, we walked down King Street and found a Christmas-themed bar we popped into for another drink. At around 11:30pm, we both looked at each other and were both relevied when the other said we wanted to go home and be able to watch the ball drop on TV. (You might be in your 30s when…) It turned out to be a great move, too, because it meant we missed all the super expensive Ubers and were in bed, with our nighttime skincare routines done just a few minutes into 2022.
Saturday morning, Emma caught the first flight out of town back to NYC—but I was on the opposite travel schedule and had a 6pm flight back to DC. I don’t mind exploring places on my own, and while I certainly missed having Emma around, I still wanted to make the most of my final day in CHS! I did sleep in until around 10am as I cannot hang like I used to—and I wanted to start the new year off as rested as possible.
I loved our walk at Pitt Street Bridge and through Old Village Mount Pleasant so much that I went back and spent about two more hours enjoying this picturesque neighborhood. January 1 was such a nice day, and being outside with the smell of saltwater in the air was just perfect. After my walk through Mount Pleasant, I grabbed an Uber over to downtown Charleston and—this is kind of embarrassing to admit—but I ate at Chipotle on King Street for lunch. I was starving and wanted something quick! (I did throw myself a Chipotle birthday party after all…) After getting my burrito bowl fix, I spent the rest of the afternoon walking around Charleston—I think I ended the day with 20K+ steps! Like I said, seeing all those gorgeous Charleston homes never gets old, especially when they’re all still decked out for Christmas. It was then time to grab my bags and head back to the airport—and despite all the holiday travel delays, I was lucky enough my flight left on time!
This trip was the perfect way to start off 2022, and it made me feel so optimistic about the year ahead! I first went to Charleston in summer 2011, and am so glad I have been able to get back many times since. If you have any questions about our trip, where we stayed, where we ate + drank, or what we did, don’t hesitate to drop a comment below or email me, firstname.lastname@example.org.