3 Days in Charleston, SC

May 22, 2019

My college roommates and I planned a 40th birthday celebration in Charleston, South Carolina. We met for wine fall of 2018 and decided to pick a city to meet up for a weekend away. Charleston was at the top of the list, the latest tourism buzz got a hold of us regarding the charm and character of this city. Without a doubt, it was a perfect getaway. Our only regret was not staying additional day or two to do all the things this city has to offer.

I was able to find so many verified recommendations from my followers on IG, some of whom live or have lived in the city. I spent some time prior to leaving sorting these out and making needed reservations so we could get in, the advice on the street is you NEED to plan ahead to fully enjoy Charleston, especially during the summer months. I will recap our itinerary below.

image: south of broad walking tour

First things first, stay in an Airbnb, the residents of this city do such a nice job of restoration and making you feel at home. This wasn’t our first pick, but now that we’ve stayed and are familiar with the location, this ended up being a perfect host location for us. The host’s were nearby, friendly, attentive and the amenities were spotless with attention to all the details. (aside from the men’s underwear we found in our bedroom closet, but hey .. one of many laughs we had all weekend).

airbnb host: Morgan, 70 Cannon Street, Unit A

Our first stop was at one of many rooftop bars this city boasts with view of the bay just off the Atlantic Ocean. We opted for Pavilion Bar, one of the busiest corners on E Bay Street (get to know E Bay Street!).

Afterward we had dinner at 5Church, this restaurant pops up in other cities in the South, but it came highly recommended and the architecture alone is worth the stop. It wasn’t our best meal of the weekend, the menu was a bit all over the place, we opted to share a few things. We didn’t stay long, while the venue was stunning we were seated in a back room near the kitchen, so there wasn’t much to see from our perspective.

5Church Charleston

We did make it out to the nightclub end of King Street, while we didn’t last long we saw the evidence of what would soon be a late night for the younger crowd. We did however pop into one bar with live music. The nightclubs are on the north end of King with the boutique shops in the middle, working your way to the larger, big box shopping as you work your way south on the peninsula.

Day 2, and this I highly recommend, we did a historical walking tour. We also booked this ahead of time through Airbnb. We had Alexandra as our guide and were lucky enough to have a private tour with just the three of us. It was so fascinating to learn about the rich history of this city, some of which was a refresh, and other information was entirely new. It certainly helped create buy in with the culture and scene of our visit. Leaving us craving more and conversation for hours to come.

we spent our tour time in south of broad, neighborhood on the southern point of the peninsula.

many homes are adorned with elaborate iron details and manicured floral window boxes.

the infamous rainbow row, which was covered with instagramers curating the perfect shot.

more iron details, window boxes and gas lamps, which most still run and operate by underground gas systems.

one of my favorite color palates, natural brick, black accent door and white trim.

many of the homes on the peninsula are this well manicured and restored.

evidence of years of restoration (or lack of). many of these homes built in the 1800’s are still family owned and occupied.

the harbor view, where homes can be sold for 10 million or more, stunning!

quaint neighborhood home, the black circular dots are beams running through the structure to secure in the event of an earth quake. although modern day evidence shows lack of reinforcements is the way to go so these buildings can ebb and flow with the ground movement. we were told they are due for a big one ..

not on the walking tour, but later we visited the veranda at Zero George Street,

may be the cutest boutique hotel in all of the city.

After our tour we had lunch reservations at the cities hottest restaurant, Husk. Off the busier streets, but walk-able to everything else. This was by far the best meal of our visit, we had traditional Southern shrimp and grits, beef brisket, corn bread to name a few. The service was also outstanding, be aware you need to make reservations well in advance.

image provided by Husk, Charleston

On our walking tour, we learned of McGrady’s Tavern, one of the most historical stops for eats. McGrady’s was built in the late 1700’s and most notable for a grand celebration dinner for George Washington. Our food was good, but I couldn’t help think it would be a fabulous elevated bar food scene .. fish and chips, gourmet burgers, fried chicken. I wasn’t expecting fine dining cuisine. Still worth a visit for the history lesson alone, but like most of Charleston the menu prices are much higher than what we’re used to in the Midwest.

Day 3 we ventured to Sullivan’s Island, not a popular tourist destination but told by the locals it’s worth a day trip. We couldn’t agree more, Foley’s is the more popular beach, so we opted to stick with the quieter route. It was only a 20 minute ride share away, by the way, my party all agreed doing ride share was the way to go, skip renting a car. It’ll take a lot of work to navigate parking, and you can’t beat door to door service. We never waited more than 5 minutes for a car as well. Once on the island, we had brunch at The Obstinate Daughter .. OMG. Run, don’t walk .. the design is spot on and the food is even better. Word to the wise, this kitchen knows their stuff, they only serve real food (no skim milk for my friend that still drinks it in her coffee 🙂 and no substitutions on the menu items. I appreciate a kitchen that has no shame in their game, and sticks to a required presentation to execute a specific menu that has been thoughtfully predetermined for all guests.

images provided by, Obstinate Daughter

vegetable frittata with a tomato base and sourdough toast, i died.

heirloom tomato bloody mary’s, i’ll take 2!

Last, but not least we had dinner at Magnolia’s. This wasn’t on our agenda, but everyone in Charleston was talking about it. We indulged with the halibut, fried chicken, and more shrimp and grits. The best was indeed the large piece of homemade pecan pie topped with vanilla ice cream. We considered having more than one ..

We also spent many hours in local boutiques shopping, coffee shops, the open air market was a fun visit, ice cream shops, and taverns to break up the day. Charleston exceeded expectations and I am longing for more. We will definitely be back, adding Plantation Tours and a sailboat ride in the harbor to the list!