Eat, Sleep, Shop & Stroll- The Charleston Guide

The Holy City is known for many things- rich history dating back to the Revolutionary War, colorful architecture, carriage rides, and courtyards, to name just a few- but “many come to Charleston with one thing in mind, the food.” Anyone can comb the cobblestone streets for sacred signature dishes like She-crab soup, Frogmore stew, hushpuppies, and boiled peanuts, but if you want to experience genuine Southern hospitality, head to some of the city’s most charming, even humble establishments. There are endless possibilities that celebrate local talent and ingredients. Still, it’s essential to prioritize unless you plan on becoming a local yourself, as it could take years to hit all the good spots.

The food and wine scene in Charleston is one that never sleeps. Even in the steamiest months of the year, reservations are still a must (especially if you want to sit inside in the air conditioning), and even then, they can still be a challenge. Here are a few helpful hints-

-Persistence is paramount in this town because tables book up months in advance. Remember to keep calling and check back the day of for cancellations as Open Table is often not updated.

-By all means, befriend your hotel concierge. Certain hotels often have a small handful of tables at preferred restaurants for just the right customer if you develop a relationship early in your stay. And a “donation” never seemed to hurt either.

-Most notably, always seek out suggestions from your trusted local bartenders. Charleston is, after all, a small town, and the hospitality industry is a tight-knit community. Suppose you play your cards right (and again, tip generously) that quintessential Southern Charm might just lead to “my girlfriend is the host at XX, let me see if they have any cancellations tonight…” or “I used to work at XX, let me call Jerry the chef and see what’s going on over there tomorrow…” Sometimes it’s not what you know but who, and that someone might be mixing your martini right in front of you. Do not underestimate the seriousness of service, standards, and social connections in this town.

Just a few places to choose from–



High Cotton

Halls Chop House

Chez Nous

Peninsula Grill


The Rooftop

Chubby Fish

Obstinate Daughter

After exploring the waterfront, the numerous historic cemeteries that dot the city, and perhaps a carriage ride with a humorous driver filled with lore galore, head to King Street for a bit of shopping. This street is a treasure trove for antique fanatics and there is no shortage of beautiful spots for furniture, silver, art, and curiosities. Check out this guide to narrow down what you’re looking for or enjoy the thrill of the hunt by exploring all your options as you wander up and down King Street.

For clothing, Charleston is known for its independently owned women’s boutiques like Hampden (which also has two exciting concept stores on King Street, James and Small) and The Finicky Filly. Still, in my opinion, the real standout of clothing boutiques on King Street is M. Dumas & Sons. Classic men’s shops seem to be a dying breed in any city across the country, so it was a pleasure to discover this classic gem where the customer service was like no other. Their tagline says it all, “a century of style, a heritage of service.” We spent hours here and enjoyed every minute of the knowledgeable and friendly staff who was ready to coordinate outfits for every occasion. They graciously shipped it all, so we didn’t have to worry about stuffing a suitcase.

Now that you’ve dined, shopped, and strolled, it’s time to enjoy the city’s finest places to rest. We stayed at The Restoration, which has a gorgeous clubby bar, butler service, and a lobby draped in deGournay wallpaper. The hotel was small, quiet, and despite the description in the last sentence, not pretentious at all. The location was ideal, just off Market Street, and the concierge was beyond helpful to assist with dinner and lunch reservations, carriage rides, and insider tips and tricks. Within walking distance, other great choices are Charleston Place (a Belmond property), Hotel Bennett Charleston, The Dewberry, Planters Inn, and The Spectator.

If you’re looking for a city steeped in history, shopping, and culinary delights, Charleston should most certainly be your chosen Southern belle for a long, enjoyable weekend getaway.

The Mom Mystique

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