On The Road: Charleston

Charleston’s Best in One Weekend


Phase One: Road Trip Planning

Traveling from Vermont to Florida on the ground, rather than in the sky, was a big undertaking. To figure out exactly what my road trip would entail, I knew that I had a lot of planning to do. I had never planned a road trip, used maps to mark multiple stops, or researched entire states to find the best towns. But once I embarked on the planning process, I came to discover two things. First, that there are not many great tips out there for road trips. And second, that each state I’d be passing through had a lot to offer, so it would be hard to decide what to see.

I knew that the first half of my trip would be the majority of the longest straight-through drives. We passed through Massachusetts, Rhode Island, Connecticut, New York, New Jersey, Pennsylvania, and Delaware without stopping. After spending a night in Annapolis, Maryland, we would drive through Virginia to North Carolina, where we’d spend several days on a friend’s farm. But after that, the world was our oyster. Or at least, South Carolina and Georgia were our oyster. And I knew there was one stop that we just had to make. Cue: Charleston.

Southern Charm

Charleston is unlike any other place that I have seen. The city has (clearly) worked tirelessly to ensure that strict building codes are met, historical places are preserved, and that the charm of the city lives on. And boy have they succeeded! The locals have innately good taste–in food, design, and culture–that fill Charleston with stunning architecture, warm colors, and delicious food. From cobblestone streets to corner cafe’s with amazing biscuits made by hand (Callie’s Hot Little Biscuits, for real), Charleston is a living, breathing moment in time that has modernized itself without changing too much. Because we wouldn’t want it to.

A Lay of The Land

Charleston is comprised of a historic downtown that sits on a peninsula, connected to neighboring islands by long bridges that pass over seemingly countless water ways.  The result? The entire area is an ultra-coastal experience that gives us gorgeous views at every turn. Whether it’s your first or fifteenth visit to Charleston, it’s always a good idea to go for a stroll along The Battery–the historic, exclusive, and breathtaking promenade on the outermost street of the peninsula. Originally constructed as a defensive seawall that served its purpose in the Civil War, it’s now lined with breathtaking antebellum mansions. Start your weekend with a walk through this gorgeous area and be sure to bring your camera, because there’s nowhere else in the country quite like it.

After getting a lay of the land and walking The Battery, head into downtown to explore. The perfect place to start is on King Street–the main strip of Charleston that’s lined with shops of literally every kind. From antiques to art galleries, book stores to boutiques, and even Versace, King Street has something for everyone. Take your time walking around, people watching, shopping, and tasting. One of our favorite stops is the historic Charleston City Market, where you can walk both inside and outside to browse local goods.

Many of the side streets that intersect with King also have troves of treasures to discover. Right off of King Street, on Society Street, you will find Christophe Artisan Chocolatier-Patissier, which is home to arguably the best chocolate in Charleston. Stop for a sweet and coffee when you’re nearby. For my fellow nerds out there, be sure to stop at Blue Bicycle Books to peruse used, rare, and local books.

Time to Eat

When meal times roll around, the list of possibilities is almost endless. We love Hominy Grill for their Charleston Nasty Biscuit–a homemade biscuit with fried chicken, cheese, and sausage gravy. Or Swig & Swine for barbecue paired with southern sides. What? I never said you’d lose weight in Charleston.

For dinner, the city has a number of fine dining options that cost a bit more, but promise as much in flavor. Our favorites are renowned restaurant Husk, the brainchild of James Beard Award-winning Chef Sean Brock. And one of the local favorites Slightly North of Broad, or SNOB, as the Charlestonians so lovingly call it. After dinner, split a cupcake with a friend at Kaminsky’s, or grab drinks at the Market Pavilion Hotel rooftop. You’ll love the view.

After spending a day or two downtown, I’d urge you to venture out to Mount Pleasant and the Isle of Palms. The two neighboring islands are home to even more things to discover. With warm waters, gentle waves, and super soft sand, the Isle of Palms beaches just can’t be missed (visitors can park close to Front Beach on Pavilion Drive). Just don’t forget to pick your jaw up off the floor when you see all the amazing homes lining the Isle. It’s also worth noting that Boone Hall Plantation resides in Mount Pleasant, and has been preserved to offer historic tours and learning opportunities to the public.

My final morning was spent on the beach, and then we finished with a stroll down King Street once more. With a coffee in hand, I was sad to leave Charleston, but I was looking onward towards Savannah.

The Quick List

Beach: Isle of Palms

Treats: Kaminsky’s Desserts and Coffee

Carbs: Callie’s Hot Little Biscuit

Drinks: Market Pavilion Hotel rooftop

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