The Road to 50: A Charleston, South Carolina Travel Diary

A few years ago I decided to formally declare the mission of visiting all fifty states. Thankfully, I had a pretty good head start and I’m twenty-six states in. As things stand, I’ve finished the west coast (yes, I know there aren’t that many states that make up the west coast, don’t burst my bubble). And I’m three states shy of finishing the east coast—I still need Maine, New Hampshire, and Connecticut. Let me know of any must-see stops in those states.

Oh, before I forget, let me take this opportunity to give a shout out to all those supporting me on this self-imposed adventure. Thank you!

This travel installment goes out to the bestie who spent my fifty-third birthday with me in Charleston, so I could knock South Carolina off my list.

Where we wandered

We had the good fortune to meet up with a friend’s daughter who is in college there, so we had a personal tour guide for part of one day. She took us to Waterfront Park, which was pretty and adorable all at the same time. Why do they have a pineapple fountain, I don’t know—but it was so fun to see.

Okay, I did a little research, apparently pineapples represent hospitality and are common in Charleston. 

One of my most favorite stops was The Paper Canopy (come on, you had to see that coming). Not just because it’s a super cute stationery store with an awesome selection but because we also had the chance to meet the owner, who was absolutely lovely. 

Her story was inspiring. I believe she had worked at a stationery store that she thought she would eventually assume ownership of one day. But that didn’t pan out. She moved away from South Carolina for a while and years later, returned and opened The Paper Canopy. If you make your way to Charleston, make this a stop.

And my friend and I wouldn’t be us if we didn’t visit an independent book store (or several), so we did. And the one that stood out most was Itinerant Literate Bookstop. A bit unassuming in appearance but with a very friendly staff and packed with more than you’d expect—including stickers! They started as a mobile and pop-up bookstore before opening their brick-and-mortar shop. I’m rooting for them.

Like most of my favorite trips, this one ended up being less about landmarks and more about the people and places I encounter.

The food and the history 

With all of this book and stationery shopping one must eat. There are restaurants aplenty and I can confidently say that my friend and I tried a lot of lowcountry cuisine. It’s very rich, flavorful and honestly—heavy. So while I don’t have a favorite restaurant, I can recommend a breakfast stop—Callie’s Hot Little Biscuit. Another friend had suggested we put this on our itinerary and it did not disappoint. We visited the counter service location in Charleston City Market but there is a sit-down flagship location on King Street.

When talking about Charleston, I feel like I have to mention Ft. Sumter, the site of the start of the Civil War. I’ve mentioned my strong interest in history, so we ferried over. As a Black woman, that particular era of history conjures a lot of feelings—anger, hurt, gratitude for how far we’ve come,  and frustration at how far we still have to go—a mixture of emotions I think are showing on my face. 

But history aside, and at the risk of sounding cliché, Charleston is a very charming city. A different vibe than the big cities I usually visit. Much smaller, a bit hotter, and dare I say, a tad friendlier. So, if you’re thinking of visiting—and I recommend you do—this may help you with more travel ideas. 

Stay tuned for more stately adventures. In the meantime, if you’ve already visited Charleston, what did you think? And if you make your way to this southern waterfront gem, come back and share your thoughts.