36 Hours in Charleston, SC

36 Hours in Charleston, SC
📍 Charleston, SC

The following content may contain affiliate links. 
When you click and shop the links, I may receive a small commission.

Dress || Sneakers || Handbag || Earrings

On our drive home from Florida to Connecticut, we decided to break up the journey with a two-night stop in Charleston. It wasn’t originally part of the plan, but it quickly became something we were genuinely excited about, especially since it was our first time visiting the city. Traveling with Brennan has taught us to slow down and be a bit more selective, which felt like the right approach for a short stay. With just about 36 hours to explore, we let the city reveal itself naturally, without pressure to do it all.

Check-In at the Palmetto Hotel

We opted for the Palmetto Hotel to be our home base during the short stay. This is an example of a boutique hotel at its finest. Centrally located, it really allowed to maximize our time in Charleston. The rooms were beautiful, they offer free breakfast each morning, and they were incredibly hospitable to Brennan. After checking in, we took a moment to settle, refresh, and let Brennan get acclimated before heading back out.

Relax at the Lobby Bar

To decompress before getting ready for the evening, we sat at the lobby bar to ease into Charleston time. Even on a Sunday afternoon, there was a constant stream of people flowing in and out, creating quite a buzz. I ordered their signature drink, the Palmetto Punch, a followed Brennan around as she explored the sitting area in the lobby.

Check-In at the Palmetto Hotel

We opted for the Palmetto Hotel to be our home base during the short stay. This is an example of a boutique hotel at its finest. Centrally located, it really allowed to maximize our time in Charleston. The rooms were beautiful, they offer free breakfast each morning, and they were incredibly hospitable to Brennan. After checking in, we took a moment to settle, refresh, and let Brennan get acclimated before heading back out.

Relax at the Lobby Bar

To decompress before getting ready for the evening, we sat at the lobby bar to ease into Charleston time. Even on a Sunday afternoon, there was a constant stream of people flowing in and out, creating quite a buzz. I ordered their signature drink, the Palmetto Punch, a followed Brennan around as she explored the sitting area in the lobby.

Explore the Gibbes Museum

I didn’t have a lot I wanted to accomplish during our short trip, but the Gibbes Museum was the star of the list. Through art, it offers a really interesting look into the history and culture of Charleston. With a mixture of 18th-century and more contemporary art I was also introduced to several artists that I wasn’t familiar with, but whose art instantly stood out to me.

Shop Along King Street

From there, we spent time browsing and shopping along King Street. The mix of well-known shops and local favorites made wandering feel effortless, even with a stroller in tow. It was enjoyable without feeling rushed or overwhelming. My favorite store, by far, was Croghan’s Jewel Box. A century-old family legacy, their estate and antique jewelry felt like a little museum on its own.

Lunch from Poogan’s Porch

The yellow exterior and two-story covered porch at Poogan’s Porch is the sign that you’re in for a treat. I will always love Southern cuisine, and I need to share a special WOW to their fried chicken with a dash of pimento cheese. Bloody Mary optional, but highly recommended.

Admire the Historic Homes

After lunch, and a quick disco nap back at the hotel to recharge for the evening, we took our time walking through the residential streets, admiring historic homes that give Charleston so much of its character. It’s incredible to learn what houses have been in the same family for over six generations.

Pre-Dinner Drinks at Little Palm

Before dinner, we headed to Little Palm, the rooftop bar located at the Ryder Hotel. With its laid-back energy and creative cocktail list, it felt like the perfect place to ease into the evening. The drinks were playful and well-balanced, and while we loved soaking in the atmosphere as a family, it’s definitely a spot we’re already planning to revisit sans Brennan for a longer, lingering stay.

Dinner at Darling Oyster Bar

As someone who never turns down seafood, dinner at Darling Oyster Bar was high on my Charleston wish list. We started with a full plate of local oysters, followed by the hot crab dip. It was rich, comforting, and surprisingly Brennan-approved. The menu felt classic yet elevated, and it was one of those meals that instantly made me understand why this spot is such a favorite.

For a first visit, Charleston exceeded every expectation. Even in a short window of time, it felt approachable and full of charm, offering plenty to enjoy. Our 36ish hours gave us a wonderful introduction to the city and left us already thinking about what we’d do differently next time, and what we’d happily repeat. It was just the beginning, but a memorable one nonetheless.

Love from Charleston,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.