An October Weekend in Charleston

If you’re in need of a relaxing Autumn weekend away, rich in culinary delight,
steeped in history, and suffused with Southern charm, look no further than a few
days spent in Charleston, South Carolina.

Founded in 1670, the “holy city” – named so for its openness to diverse faiths and home to more than 400 church steeples – boasts notes of Low-country Gullah culture amid Spanish, English, French, and German architectural and culinary influences. This beautiful city, with its small town warmth, is an abundant melting pot, just waiting to delight your senses.

Navigating Charleston is a breeze. Driving in – or flying in to an awaiting car rental – is the way to go. With so many areas to explore, having a set of car keys at your disposal is a must. But you’ll want to pack a good pair of walking shoes as well. Using your downtown Historic District hotel or B&B room as your base, you’ll find so much within a 10-minute stroll, everything from historical – and occasional haunted – walking and carriage tours, museums, fine dining, and surprises around every corner.

A casual walk down King Street offers unique shopping opportunities, architecture to dazzle the eyes, centuries-old red brick walls, and masterfully constructed church buildings, each showcasing breathtaking stained glass windows, open doors, and knowledgable docents eager to offer tours to visitors.

Turn a corner toward Meeting Street, and you’ll be delighted to find an inviting archway, encrusted with ivy and paved by a cobbled foot path – accepting the invitation to step further will reveal a mysterious and near-magical place of reverence: a crumbling cemetery, dripping with Spanish moss and sunlight, each headstone a masterpiece of artistry and craftsmanship.

The surprises don’t stop there. Charleston is the Mecca of Soul Food. Any number of eateries can be found down each thoroughfare. Craving fried chicken? Indulge at Bertha’s Kitchen, replete with collard greens and classic Southern sweet tea. Carbs more to your liking? Find the best – and we do mean the absolute BEST – stoneground grits, slow-cooked and swimming in heavy cream, at Poogan’s Porch. Fine dining more your flavor? The folks at 82 Queen will serve you a meal to end all meals, with impeccable table side service, free- flowing wines uniquely paired with each course, and rich flavors the likes of which appear only in Scarlett O’Hara’s dreams. And don’t forget brunch! Charleston’s very own Millers All Day takes this humble meal and elevates it to the art of mastery with butter-drenched biscuits, tomato jam, fried okra – yes, really! – and perfect Eggs Benny alongside your icing-soaked cinnamon roll.

This is the face of a well-fed girl, high on cheesy-grits goodness.
Sweetgrass Baskets, handmade by local Gullah women

And when you feel you’ve exhausted all the historic district has to offer (when in reality, you’ve barely scratched its charming surface), it’s time to partake in a morning perusal of the local shops of Historic Charleston City Market, before spending an afternoon at the base of Angel Tree, the South’s oldest Lady: a 600-year-old Southern Oak, her arms twisted and gnarled, her roots deep in the loamy South Carolina soil.

Angel Oak Tree

Lastly, enjoy a charter out to Fort Sumter National Monument before enjoying a sunset sail, catching Charleston’s stunning skyline against a flaming sky.

Charleston skyline at sunset

Your weekend in Charleston will be the time you find a new home away from home. You’ll feel you’ve made a new, lifelong friend, vowing to return again (and again), to savor her flavors and luxuriate in her past.

Ready to explore Charleston, SC for yourself? I’d love to be your booking agent. Please reach out, and we’ll get started planning the perfect weekend getaway:

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