How To Make the Most of Your Trip to Charleston
In Charleston, there is something whimsical everywhere you look: in the pastel-hued row houses downtown, in the glittering chandelier of a storied hotel, in the taste of a perfect oyster (washed down with well-aged Champagne, of course). It’s this whimsey — mixed with coastal charm and melt-in-your-mouth gastronomy — that makes this little city a big overachiever. Charleston, I love that for you.
It’s no surprise that Charleston’s siren call has attracted travelers from all over the world, including weekenders & brides-to-be (myself included), plus foodies & families. But despite its popularity, the South Carolina city remains delightfully at ease — which is exactly its appeal.
But with so much fanfare surrounding Charleston, choosing what to do, where to eat and how to experience the city can be a challenge. I got you.
Consider this your how-to guide to making the most of your time visiting Charleston, whether you’re a first-timer or looking to level up your next trip.
Ready to go to Charleston, South Carolina? Connect with me to plan your trip.
Step 1: Stay in style at The Dewberry Charleston
Image courtesy of The Dewberry Charleston
If Charleston is the story, then this hotel is the main character. I'm obsessed with The Dewberry Charleston because, like the very best city hotels, it functions as much more than a place to stay: a veritable city landmark, The Dewberry Charleston is just as much of a local hotspot and community treasure as it is a luxury hotel.
And luxurious it is. The Dewberry Charleston has all the trappings of a five-star grande dame, including a regal terrace bar (The Citrus Club), sumptuous spa and opulent guest rooms. The Dewberry Charleston is also prized for its 10/10 location, located just off Marion Square at 334 Meeting Street in the heart of the historical city of Charleston. Marion Square is the former Citadel Green and the largest Park in the historic district.
Image courtesy of The Dewberry Charleston
And while five-star Southern hospitality is infused into every element of The Dewberry Charleston — including its dining, outfitted with mid-century furnishings, a curated reading library and a showstopping brass bar, the Living Room is a warm and welcoming destination. Honoring the history of the landmark L. Mendel Rivers Federal Building (circa 1964), The Dewberry captures the luxury and quiet restraint that are hallmarks of historic Charleston. Founder John Dewberry’s vision of “Southern Reimagined™.” As much a setting as it is a state of mind, the hotel was brought to life over eight years by a team of architects and designers who shared Dewberry’s mission to present Charleston from a uniquely personal perspective.
Connect with me to book a getaway to The Dewberry Charleston, and unlock perks:
$45 per person daily breakfast credit (max $90 per room)
$100 hotel credit (Available to be Applied Towards Spa, Living Room or In-Room Dining, Citrus Club, Valet, Airport and Local House Car Transfers)
Upgrade, based on availability
Early Check-in/Late Check-out, based on availability
Step 2: Soak in the atmosphere — and hear Charleston’s stories
Your next assignment: lean into the city and learn what it’s all about. If you’re a first-time visitor, take a carriage tour of Charleston’s historic district, with its cobblestone streets, candy-colored houses and 18th-century churches. Known as Rainbow Row, the historic homes and flower-filled window boxes are definitely a highlight.
But while the elegant architecture and leafy streets are charming on the surface, they tell a story that is quite the opposite. Charleston’s history of enslavement, and the city’s prominent role in the institution as a whole, cannot be ignored. Visiting Charleston means engaging with this history, and hearing these important stories. This summer, the International African American Museum opens on downtown Charleston’s waterfront. The 100,000-square-foot museum is a highly anticipated addition to the city's evolving identity.
Step 3: Experience the food scene
Image courtesy of Sorelle
Remember that melt-in-your-mouth gastronomy I was talking about? Let’s break it down. Visiting Charleston means indulging in its internationally lauded food scene, with cuisines ranging from classic Southern Lowcountry (think shrimp & grits) to elevated coastal fare (oysters on repeat).
My top choice for a big night out is Sorelle, the contemporary Italian-meets-Southern eatery that opened in March and is already regarded as a Charleston institution. Between the all-day market, pizza & wine bar and refined dining room, Sorelle is worth it only for a taste of their ricotta tortellini. These are affectionately known as ‘Pillows of Gold’ (and I agree).
Locals and visitors flock to The Charleston Place Hotel for lunch at Palmetto Café, which features a dreamy garden setting and fine dining (get the crab soup). For a sophisticated dinner, the hotel's Charleston Grill offers an exceptional wine list and elevated Southern cuisine. If you're craving something slightly more casual, Leon's Oyster Shop, Home Team BBQ and 167 Raw Oyster Bar are all great choices for standout Lowcountry cuisine. And I love the Thoroughbred Club for cocktails by the fireplace.
Step 4: Do as the locals do
Sullivan's Island
To make like a local in Charleston, there are a few items on your to-do list. Couples & bon-vivants should soak in the city’s distinctly European vibe with a stroll through the French Quarter, featuring historic homes (some of which are historic sites in their own right). Next, a wellness moment at the spa. My luxury hotel pick, The Charleston Place, offers a 10/10 spa experience, between its rooftop pool and signature massages.
While shopping on downtown Charleston’s King Street (where else?), hit what’s known as Lower King Street for antiques, and Middle King Street for fashion. While exploring, check out Charleston City Market, a prized part of the historic district, and Charleston’s harbor and waterfront park. Another local-approved moment: catch a show at the Egyptian Art-Deco (yes, you read that right) at the Riviera Theater. The arts venue is a lovingly conserved piece of King Street’s history.
Your last assignment in visiting Charleston, South Carolina: Sullivan's Island for lunch and a beach walk. This breezy beach town is just across the bridge from downtown Charleston and makes a perfect day trip. For a meal on Sullivan’s Island, I love the Obstinate Daughter (great for lunch or a gelato after the beach). For more natural wonders, take a boat ride through scenic Lowcountry or a jaunt to beloved islands: Folly Beach, Kiawah island and Isle of Palms.
Ready to go? Connect with me to plan your trip to Charleston, South Carolina.
