Repeatedly named “City of the Year” by Southern Living, I definitely had high expectations for our first trip to Charleston. And it ended up being even better than I imagined! Alex and I were in awe of the beauty and history of every stop along our path. Truthfully, I have no idea where to even begin with posting about our trip to Charleston. After thinking it through, I think the best thing to do is to start with an overarching travel itinerary. I hope this is helpful if you’re planning a trip! (And if not–you must!)
Our goal was to see as much as we could, and we definitely accomplished that! My biggest tip for a 4-night trip is to schedule an early flight into town and a late flight out–that essentially gives you an extra day to explore! While I always wish that we had extra time on trips, I do think that our Saturday-Wednesday itinerary gave us plenty of time to explore Charleston.
WHERE WE STAYED
There are so many beautiful hotels and inns in Charleston–it was honestly a bit overwhelming when I first began booking our trip! After comparing a few options, we finally landed on Hotel Emeline and it was a fantastic choice! We ended up choosing Emeline based on the proximity to the beautiful South of Broad neighborhood and King Street–both places that we knew we’d likely want to spend a lot of time in! They also have complimentary bicycle and Mini Cooper access, which made our trip even more fun! If you’re like us and looking to book a hotel in CHS on a budget, definitely look at their promotions. We were able to get our 4th night free, which made Hotel Emeline just as affordable as some of the smaller bed-n’-breakfasts we had considered!
Day One // Travel & Our First Taste of Charleston
Truthfully, I put a lot of time into researching the best places to sightsee, eat, and shop on our trip, and I’m so glad I did! Had I not done research beforehand, I think I would have become overwhelmed by the options. After dropping our bags off at the hotel, we went out for a light lunch. We landed at Caviar & Bananas, which ended up being exactly what we were looking for! Just off of King Street, they had one of the best sandwiches Alex had ever had.
After lunch, we did a bit of shopping on King Street and I was so excited to see Amanda Lindroth‘s beautiful shop in person! I ended up finding the most adorable Rattan basket bag (on sale!) and I know that it will be a keepsake from this trip for years to come.
We headed back to the hotel to check in and change for dinner and were welcomed with a sweet anniversary gift from the hotel staff. It was so thoughtful and made our stay even sweeter! For dinner that night, we ate at Frannie & the Fox, the restaurant in the courtyard of our hotel! Because we knew we’d be eating a lot on this trip, it was nice to split a wood-fired pizza together. They also had fun cocktails!
After dinner, we walked around South of Broad and quickly fell in love with the history and character that each home possessed. From cobblestone streets to ivy-arched pathways, this area is a can’t-be-missed area! Waterfront Park is also nearby, which holds the iconic Pineapple Fountain and plenty of benches to rest and take in the beauty of the surroundings. To end the evening, we made our way back up King Street for dessert at Off Track Ice Cream before heading off to rest for the day ahead.
DAY TWO // FORT SUMTER & OUR ANNIVERSARY!
We were very ambitious about getting a lot out of our trip. I think the key is to schedule a few key items and leave a lot of room for exploring. That’s exactly what we did, and it kept us from getting overwhelmed while it also gave us free time. To start the day, we went right across the street to Callie’s Hot Little Biscuit inside the French Market. It was so good, and it ended up being where we went each morning! If you are there early enough, get a fried chicken biscuit. I loved getting the mini trio (and selected sharp cheddar, black pepper bacon, and birthday cake biscuits!).
After breakfast, we made our way up to Liberty Square for the Fort Sumter tour. This was high on Alex’s priority list, and I found it to be more interesting than I anticipated! The only downside to this part of our day was that we got caught in a storm while at the fort and were completely soaked! But thankfully the warmer climate helped us dry off in no time. And now we have a memory we’ll never forget!
Rather than locking us into reservations for every meal, we opted to play it by ear for breakfast and lunch each day, which gave us the flexibility to see where the day took us. We had no problems getting a table at the restaurants we chose each day, and it was nice to have a little less structure built into our days. For lunch, we went to Miller’s All Day and it was delicious. It was right on King Street, which made it convenient for shopping, and was near our hotel!
I know it probably sounds like all we did was eat (and we did a lot of that!) but walking 90% of the time gave us healthy appetites. After a full day, we freshened up and headed to dinner at Chez Nous–a pint-sized neighborhood restaurant. This spot came highly recommend for its ever-changing, handwritten menus and romantic atmosphere. To end the day, we made it to the Rooftop at Vendue for sunset views and drinks. Recently named the best rooftop in Charleston, it was a fun atmosphere and a great way to cap off our first full day.
DAY THREE // A WALKING TOUR
On our third full day, we scheduled a morning walking tour with Bulldog Tours and it was just what we hoped it would be! After grabbing a few mini-biscuits from Callie’s, we walked over to our meeting spot to begin to tour. We were easily the youngest in the group (by about 20 years–haha!) but it was so fun to walk around the historic South of Broad area with a guide who was so knowledgeable about the history of Charleston. When our tour ended, we headed to SNOB (Slightly North of Broad) for lunch at our tour guide’s recommendation. Our afternoon was open to explore the area, and we did just that!
After resting and regrouping, we headed to Husk for a later dinner and it exceeded all of our expectations. If you go, be sure to try the Charleston Light Dragoon’s Punch (A recipe from 1792 discovered in the Preservation Society of Charleston’s archives!). Following dinner, we walked around the neighborhood and stopped by Kaminsky’s for dessert before calling it a night.
DAY FOUR // A DAY TO EXPLORE
On Tuesday we took advantage of our hotel’s bike service and rode through the beautiful neighborhoods and parks of Charleston. I, truthfully, was not so sure how it would go. Charleston roads can be pretty busy! But thankfully they have ample bike lanes and many of the streets we rode down were not busy! We took a short break at The Battery and it was so nice to just sit and enjoy our surroundings.
After returning the bicycles, we opted for an early lunch at 167 Raw before going back down King Street for Alex to buy a pair of On Cloud sneakers he had spotted the day before. It was so fun seeing how proud he was of his purchase! There were also many local shops & stores to browse around on King Street, and as a long-time fan of LAKE Pajamas, it was fun to visit their storefront, too.
The weather was perfect on this day, so we decided to stop by the Citus Club–a rooftop bar at The Dewberry Hotel–and it gave us the most incredible view of the city! If I could do this trip over again, I’d go there multiple times just for the view–haha! Our dinner reservation was for later in the evening at the Darling Oyster Bar, and just like our other meals, it was incredible. Definitely get the baked oysters (I especially loved the Alabama White Sauce & Bacon topped oysters!).
As this was our last full day in Charleston, we were definitely feeling especially sentimental (haha–does anyone else feel this way on trips?) so we went back to The Battery to watch sailboats out on the water. It was so quiet and peaceful–a great place to reminisce on the fun we had had!
DAY FIVE // SULLIVAN’S ISLAND & THE TRIP HOME
While this was a shorter day, it may have ended up being one of our favorites! Alex reserved our Hotel’s Mini Cooper, which gave us the chance to explore beyond downtown Charleston. I had done some research on the area prior to our trip and knew that if given the opportunity, we should head over to Sullivan’s Island. I am so glad that we did! It was so fun to see the Lowcountry and to walk out on the beach at Station 18 1/2. Growing up near the Gulf of Mexico, it was fun to see the similarities and differences between the beaches. Alex and I both loved how the shore was wide and flat–perfect for walking! We also loved seeing the locals bring their dogs out to play (although it made us a little bit more ready to head home to see Archie!).
After making our way back to Charleston to return the Mini Cooper, we went to the highly recommended Poogan’s Porch. The atmosphere was super southern and the food was just as good as we hoped it would be! Tip: check out the old menus signed by celebrities in the main hallway–it was so fun to see names like Barbara Streisand on the wall alongside things like $0.35 coffee!
We made our last shopping stop for a store I had been meaning to visit the whole time: Cabbage Row by Needlepoint.com! Needlepoint seems to have made a resurgence over the past few years, and I had been admiring it from afar because I was unsure how to get started. I was so happy I got to stop in and see the handpainted canvases in person! The ladies there were so helpful and set me up with exactly what I needed for my first project. (And now… I’m hooked! But that’s a blog post for another time).
Here’s where our day got interesting… Because we used my tip I mentioned earlier about booking departing flights for later in the day, we had a full day in Charleston before heading home… or so we thought! Our flight to ATL was canceled (and I received the email while we were in Cabbage Row!). I calmly checked out and immediately told Alex about the dilemma when we left the shop. Thankfully, some quick thinking on Alex’s part got us on a flight from CHS to LGA and then back to MEM. It really didn’t cut out that much of our day, but it did leave us feeling a bit frazzled. All in all, we ended up landing at Memphis at the same time as we had originally planned… it was just a bit indirect!
Leave a Reply
You must be logged in to post a comment.