How to Spend Three Days in Charleston, South Carolina

Y’all…I’ve found the place that makes my heart happy.

After years of wanting to visit Charleston, one of my best friends and I decided that since we hadn’t seen each other since her wedding, we were due for a girls weekend, and chose to go to my now-favorite city. It was such a fun place to explore together, and catch up on everything. There’s something so special about a friendship where you can not see each other for a long period of time, but when you reunite, it’s like that time apart never happened.

Charleston (or how they say it in the South, Ch’yallston), has everything I’ve ever wanted in a city: a cute, historic downtown, the beach, proximity to other places I love (Savannah, GA, Hilton Head, SC, Raleigh, NC), and year-round warm weather. Say what you want about the heat and humidity; I’ll take it over a midwest winter any day.


Day One

We arrived in Charleston late afternoon, so our first stop after dropping our bags at the cutest AirBnB, was dinner at Leon’s Oyster Shop. This place is adorable, and had amazing food. I got a mahi sandwich and frose’. What a perfect way to start vacation 😉

Of course, I had a laundry list of places to check out, so next was The Rooftop at the Vendue. Even though it was dark, it was cool to check out the city from above, while sipping spicy margaritas, of course. The one thing to keep in mind when coming here, is that the only way to the top is by an elevator which holds 8 people, so there can be a bit of a wait at times. Regardless, totally worth it!


Day Two

A little background: I lived in North Carolina for about a year and a half, right after graduating college, which is when I fell in love with all of the best parts of the South; namely the food.

That being said, when I’m back, I have to visit my favorites. We had breakfast at Bojangles, aka the home of the best fast-food biscuits you’ll ever eat, and ironically the only restaurant within walking distance of our AirBnB. Some things are just meant to be 😉

Next, we ventured to Sullivan’s Island. There are several beaches in Charleston, but we ended up going here both days since it was closest to where we were staying (Mount Pleasant area), and wasn’t at all crowded. Each part of the beach is a certain “station”, and we were dropped off at Station 22. We saw a LOT of jellyfish and a few crabs washed up on the shore, which is normal for the area. The area is really cute, with decent shopping and several restaurants.

We ate lunch at The Obstinate Daughter, just a quick walk from the beach. I cannot recommend this place enough. We both ordered the shrimp roll, pictured below, and I almost cried when I saw they had my favorite beer on the menu! Life was good today.

Later, we went downtown to explore. Some must-sees when in Charleston include the Pineapple Fountain at Waterfront Park, and Rainbow Row. These are within close proximity to each other, and in between you’ll get to check out some of historic downtown Charleston. See why I’m falling in love with this place, yet?



Tonight, we had dinner at Paw Paws, (low key probably gained 10lbs on this trip), and it was unreal. We sat at the bar and shared buttermilk biscuits, blue crab dip, and fried brussels. *Drools over memories*

Afterwards, we took a stroll around the city market, where vendors set up booths with all kinds of handmade goods from art to leather bags to jewelry and food. I bought a small painting of the pineapple fountain, since it’s an iconic spot in Charleston, and plan to hang it up in my home office, along with the rest of the art from my travels!

We capped off the night at the Market Pavilion Hotel Rooftop Bar, and wow, this place is like the hidden Vegas inside Charleston, with gorgeous views, an awesome DJ, and people watching.

Day Three

After taking several expensive Ubers and waiting way too long for each one (I’m not sure if Charleston just doesn’t have a lot of Uber drivers or what, but no matter where we were – Mount Pleasant, Downtown, or the beach – it took at least 20 minutes for an Uber to get to us, every time, and they were $$$), we decided to rent a car for our last day, since there was so much we still wanted to do.

This also allowed us to drive through Cookout, another Southern fast food favorite of mine, and then head back to Sullivan’s Island. Parking was free and fairly easy, which was surprising to me in such a popular area.

Later, we met another friend of mine for dinner at Tavern and Table in Mount Pleasant, which was ah-mazing. We shared apps (my favorite way to do dinner), including the crab dip (duh), cornbread, and deep fried deviled eggs. The Mount Pleasant area is definitely up-and-coming, and is adorable. It’s right on the water, and several restaurants, breweries, and shops call it home. This would be a great area to stay in if you want to avoid the higher prices of downtown.

Day Four

We spent the morning at our AirBnB’s neighborhood pool, and then headed off to Boone Hall Plantation. Also in Mount Pleasant, this is one of the oldest plantations in the country, and was absolutely stunning. It was so interesting to learn about the history, and that the current owners still live in the plantation home today! Fun fact: the house was Allie’s parents summer home in The Notebook, AND Blake Lively and Ryan Reynolds’ wedding venue!


The home tour guide was hilarious, and we loved exploring the gardens and grounds. If you’re a bird, I’m a bird, amiright?

Before we got to Charleston, I made reservations at Husk, one of the most talked about restaurants in the area. (They also have locations in Nashville, Savannah, and Greenville, as well). I’m pretty go with the flow when it comes to choosing where to eat, but Husk is known for their cheeseburger, and I wasn’t about to miss out on that! The restaurant is in an old house, and is a very classy setting. 10/10 would recommend, and definitely get the cheeseburger.

Walking off the food was necessary, so we shopped along King Street for awhile, and then, sadly, went to the airport.

I know I already said this was my new favorite city, but seriously, if you haven’t been yet, GO! My boyfriend and I are going back at the end of June, and I seriously can’t wait. There are still a ton of things I want to do and see there, and it’s just such a magical place. Until next time!


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