ITINERARY: Weekend in Charleston, SC

The American South. It’s hot, hospitable and one of my favorite places to be. For our first wedding anniversary a couple of years ago we spent a fun long weekend getting to know this southern charmer. It’s rich, albeit troubled, history is soaked into every building and every person. Check out our itinerary from our romantic three-day getaway in Charleston, SC. 

Friday (Day 1): Let’s Hit The Road

8:20 AM: Dallas Love Field (DAL) to Charleston International (CHS)

12:30 PM: Pick up our rental car; we recommend National or Enterprise. You will need a rental car in this city. If you have the American Express Platinum (or other premium travel cards) you gain Gold Status earning you upgraded rentals – nice!

1:30 PM: Lunch at Lewis BBQ. We loved this place. (Editor’s Note: This was written before we transitioned to a more plant-based diet) It’s a sprawling indoor/outdoor BBQ joint that hits all the high notes on taste, design, and friendliness – everything you should expect from a southern ‘cue restaurant. 

3:00 PM: Check-in at The Belmond Charleston Place. This hotel, y’all. My husband was going big for our first anniversary and this place did not disappoint. The rooms are gorgeous and the service was truly excellent.

Another great option for a luxe stay in the city is The Dewberry. I stayed at The Dewberry on a  trip with my mom and it’s just as nice with a more contemporary style. 

3:45 PM: Explore Waterfront Park. We take our obligatory photo in front of the huge Pineapple Fountain, dip our toes in and breathe in the coastal air. (Fun Fact: In Charleston, the pineapple represents hospitality and was traditionally gifted to house guests. I’m also told it was often placed politely at the foot of the guest’s bed to signal it was time for them to head home. You have to love the “Bless Your Heart” passive-aggressiveness Southerners have.)

4:15 PM: Historic Tour with Palmetto Carriage Works. Put aside your angst about being a “tourist” and just sign up! It’s a peaceful stroll around the gorgeous historic district with knowledgeable and kind Tour Guides. This is the perfect way to get your bearings and discover some places you might want to check out later!

8:00 PM: After a pre-dinner drink at the hotel lobby bar (lovely, great selection!) we dine tonight at The Charleston Grill at the hotel. The Charleston Grill has live jazz playing every single night and they are SO talented! It completely sets the scene and they even brought us some celebratory champagne and dessert for our anniversary. Again, the service here! I also recommend checking out The Peninsula Grill as an alternative. It’s a bit more traditional, but it’s a classic option for fine dining in town. 

10:00 PM: Drinks at the Gin Joint. Jordan and I love, LOVE a well-made cocktail. Tucked back off of East Bay Street you will find the coolest little spot to imbibe. The bartenders know their stuff and pass my “surprise me” challenge with ease. 

Saturday (Day 2): Let’s Go To The Beach

10:00 AM: Breakfast at The Hominey Grill. Okay, expectations are important so I’ll set yours for you. You’re going to have to wait on a weekend. But don’t fret! They have a gorgeous patio and walk-up window serving cocktails and coffee so grab a treat and settle in under the oak trees.  You won’t be disappointed by the food either! 

11:30 AM: Drive to Folly Beach! You can bring your own or rent chairs and umbrellas on the quintessential East Coast beach. Personally, I think it’s a must to hit up any of the numerous beaches around to truly get the full experience of the area. They are easy to get to and come on, it’s the beach!

2:00 PM: Lunch at Rita’s. Alright, the downside to a small beach town is the lack of choice in food. We didn’t love Rita’s. We didn’t even really like it. Next time we’d go for Black Magic Café

3:00 PM: Drive to Angel Oak Tree. This is another stop where you’ll have to embrace your inner tourist. It’s a tree. I know, that seems lame but it’s HUGE. Truly it’s worth a quick (and free!) stop to see the super old, super sprawling piece of nature. (More on The Angel Oak Tree)

7:00 PM: Dinner at Minero. We are Texans through and through and rarely can resist Mexican food. This spot has a great atmosphere, good menu, and solid drinks! What’s not to like? (Editor’s Note: Due to COVID-19, they have since moved to a location in St. John’s Island)

8:30 PM: Walk through the Charleston City Night Market. This is a must-do! It’s a breezy outdoor market full of locally made goods and crafts. I still pine for my own sweetgrass basket but alas, not in the budget yet. 

9:30 PM: Drinks at the Thoroughbred Club. This is the lobby bar of our hotel, the Belmond. Again, a wonderful selection with stellar service. Also, the moody wood-paneled walls just really up the southern charm factor.

Sunday (Day 3): Still Time for More

9:00 AM: Breakfast at The Palmetto Café. Hands down my favorite pancakes I’ve ever had. This spot, again at our hotel (what don’t they have here?!), is a bright airy space with a beautiful center garden you can see from all angles. It was just the thing to cheer me up on our last day in town.

10:30 AM: Drive to Middle Place Plantation. Now, I would be extremely remiss if I didn’t address the elephant in the proverbial room. The history of colonization, slavery, and general evil behavior by those who came before us hangs heavy at a place like this. I was hyper-aware of what went on here, even when admiring the beauty that this land is. 

Personally, I do think it’s worth a trip to see for yourself, not just for the landscape but to really have it sink in what we as a country, or race, are capable of. The folks here did a decent job of honoring and shedding light on the people who were enslaved here and I think their lives are worth knowing and remembering. Don’t you?

We had a quick lunch onsite at the Plantation and then departed for the airport to wrap up this weekend getaway.

Charleston quickly became a favorite of mine so below are just a few other suggestions I have enjoyed in more recent trips:

  • The Tavern at Rainbow Row: America’s oldest liquor store, established in 1686! They have so many unique bottles to peruse, any of which would make perfect souvenirs. They often have free tastings as well!
  • Rainbow Row: The historic lane of brightly painted homes makes for a great Instagram shot as well as pretty scenery to walk off the free booze from the Tavern.

If you enjoyed this post and would like to support us in creating more content like this consider subscribing to our YouTube channel!

Sign-up for our e-newsletter below to be notified as soon as new posts are released!

Sign Up!

* indicates required