How to Do Charleston in a Weekend

“Charleston has something for everyone, rain or shine.” – Thomas Gibson

For our one year anniversary, my husband and I decided to do a weekend in Charleston. He’d never been there and I hadn’t  been there since I was a child. 

We didn’t want to take any vacation time so we were successfully able to do Charleston in a weekend with leaving early on Sunday. Here’s how we did it:


Friday, October 13th

5:30 PM:   Leave for Charleston

Living north of Charlotte, it took us about 4 hours with rush hour  traffic to get to Charleston. It didn’t nearly take as long on the way home. 
9:30 PM:   Check-in at The Elliott House Inn 

The Elliott House Inn was perfect for a short trip to Charleston. It’s within walking distance to all the major places as it’s located at the section of King and Queen.  Plus, it’s right next door to the famous Husk and Poogan’s Porch. 

If you’ve only got a short amount of time in Charleston, I would definitely suggest staying within walking distance. The place was quite pricey (about $900 for 2 nights). However, you got complimentary breakfast, wine & cheese reception and bikes to tour around on. 

10:00 PM:  Drinks at The Gin Joint

This is one of the coolest bars! It’s themed like a 1920’s speakeasy – even the music is phenomenal. My favorite part is giving the bartender 2 words and then they come up with a drink. 

My husband said strong and smokey. I said sweet and savory. Both drinks were phenomenal. 

11:00 PM:  Drinks and a late night snack at Mac’s Place

We loved The Gin Joint, but wanted to get out and explore some more bars. While the service at tables was horrible, our bartender was great! He even gave us a discount for our anniversary. 

The neat thing about this bar is that they have a cool list of shots that are absolutely delicious. My husband had the Irish Car Bombs and I enjoyed the Irish Pancake that you chased with OJ.

Saturday, October 14th

7:30 AM:   Complimentary breakfast in bed at The Elliott House Inn 

The breakfast isn’t the best, but it’s nice that you can eat in your room or in the courtyard. Plus, they’ll give you a call to let you know they’ve placed your food in the courtyard. 

9:00 AM:   Shopping at the City Market

The City Market has some beautiful things for sale. We ended up buying a few little trinkets to take back with us including a leather wallet for only $29, a handcrafted ring for $20 and a pair of sunglasses for $12 since I forgot them and it’s impossible not to have them in Charleston. 

10:30 AM:  Historic carriage tour 

This was by far my favorite thing on the trip! The carriage tour was informative and we got to see a great part of historic Charleston. Plus, it was covered and kept us out of the heat. Our tour guide, Ben, was fantastic and funny! 

You can buy tickets online or from a man at a kiosk next to the City Market. The company is called Charleston Carriage Works.

These tours are regulated by the state and you don’t know which section of Charleston you’ll get to see until the tour has begun. Luckily, we got the best area, Rainbow Row and the Battery. 

11:45 AM:  Walk along the Waterfront Pier

The pier is a great place to relax – definitely try to snag a swing if you can. Unfortunately, they were all taken when we were there.

12:15 PM:  Drinks at Fleet’s Landing

Since we got there early, we decided to have a few drinks at the bar. Our favorites were the The Milagro Mule (mine) and The King and I with bourbon for my husband. 

1:00 PM: Lunch outside at Fleet’s Landing

This restaurant was amazing! We got to sit outside (in the shade) looking at the bay. Since it was our anniversary, our server gave us two free glasses of champagne. 

You’ll definitely need reservations. We made ours about a month in advance. 

2:00 PM: Self-guided walking tour along the Waterfront Park

We enjoyed walking off our lunch through the park and visiting the famous pineapple fountain. Honestly, not sure why everyone’s so obsessed with it, but it was a nice place to get out of the sun. 

2:30 PM: Touring the Old Exchange Building and the Provost Dungeon 

After the carriage tour, we were intrigued to learn more about this particular building. Inside was a nice little museum and guided dungeon tour where they locked up famous pirate prisoners and patriots. 

Tickets are around $10 per person with special discounts for teachers, military and seniors. 

It’s a real treat if you can talk to Sheriff – he’s been at this historic site for 20 years. They even have a portrait dedicated to him. 

3:30 PM: Self-guided tour through Charleston on the way back to the Inn

We enjoyed walking down all of the neat little streets and reading the plaques on the old homes and churches. We even got to stop by one of the oldest liquor stores or so it claims. 

Love the streets of Charleston!

4:30 PM: Naps at the Inn

6:00 PM: Wine and cheese reception in the courtyard 

7:30 PM: Dinner at Husk

Everyone had been raving about this restaurant called Husk. So when we called for reservations on Saturday, they were completely booked up. Luckily, it was right next door so my husband put our name down while I was getting ready. It was a 2.5 hour wait! 

The venue was beautiful! We sat upstairs on a porch and ate by candlelight. Here’s the disappointing part…the food was mediocre and way over priced. The oysters were tiny and the sauce was horrible. 

While everyone else may recommend it, I would suggest going somewhere else. 

9:30 PM:  Visit to the Savanah’s Candy Kitchen of Charleston 

On the way to our night tour, we stopped at the best candy store! They had these Rice Krispies treats dipped in chocolate and for only $5. Can’t forget about the public restrooms they offer – you’ll probably need to stop by there once or twice. 

10:00 PM: The Dark Side of Charleston Walking Tour 

Originally, we had booked our the ghost graveyard tour. However, after hearing from this group at Fleet’s Landing, we decided against it. They said it wasn’t very good. 

Bull Dog Tours allowed us to change ours to the Dark Side of Charleston. We are so glad we did! Our tour guide had actually developed this tour when the company very first started. He was a native of Charleston with a family who had been here for generations. 

It was interesting to learn about JFK, Lavinia Fisher, the British king and brothels. Kids are not allowed on this trip. 

My only complaint is it didn’t last long enough! 

Sunday, October 15th

9:30 AM: Brunch at Poogan’s Porch

We originally had reservations for 10:30 AM, but decided we wanted to get on the road a little early. So, we walked in and they seated us right away. 

This was my husband’s favorite restaurant! The biscuits and gravy were the best thing on the menu. 

10:30 PM: Walk on the Battery and through Battery Park

It was extremely hot so I was glad to get to the park where it was nice and shaded. The walk wasn’t horrible and there was this lovely man whistling “Amazing Grace” for everyone to hear. 

11:30 AM: Shopping at City Market

We want back to City Market for one last go around. That’s when we really bought most of our purchases. 

12:00 PM: On the road again 

While we wanted to do Fort Sumter, we decided to head back to our adorable fur babies waiting for us at home. We had an amazing visit and plan on coming back for a weekend on Sullivan’s Island where we can then do Fort Sumter. 

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