How to Spend a Perfect 48 Hours in Charleston, South Carolina

cobblestoned street and historic buildings,usa
How to Spend a Perfect 48 Hours in CharlestonPeter Unger - Getty Images

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

Welcome to VERANDA's Weekend Guides, where we show you how to make the most of 48 hours in our favorite destinations. When it comes to design, architecture and shopping with a side of southern hospitality and delicious food, there's nowhere quite like Charleston, South Carolina.

We tapped Jaimie Dewberry, Charleston tastemaker and owner of The Dewberry Hotel, to help us curate the perfect weekend in her city. Whether you’re an architecture buff, foodie or nature lover, there’s something for everyone on this fun and action-packed Charleston itinerary. Here’s where to stay, eat and play in this historical southern city.

Friday Afternoon

john derian suite dewberry hotel charleston
The John Derian suite at the Dewberry HotelDewberry Hotel

Jaimie Dewberry says, “The only place to stay is The Dewberry, of course!” While we think she may be a little bit biased, several of our editors have stayed at the hotel and can confirm: It’s absolutely fabulous. Make sure to book the John Derian suite if it’s available; its curiosities and creature comforts will appeal to any design lover.

After checking in to your room, take a quick 10-minute walk over to Babas on Cannon, located right off bustling King Street. Dewberry says her go-to lunch dishes are, “the pickled shrimp salad or pistachio and Parmesan salad.” The peanut mocha (made with peanut milk and chocolate) is a sweet way to end the meal and get a little caffeine boost after a day of travel.

south carolina, charleston, historic downtown, king street, shopping and business district
Jeff Greenberg - Getty Images

Once you’ve had your fill, walk to King Street to get a taste of downtown and shop at some fabulous boutiques. For clothing, Dewberry recommends Hampden, Veronica Beard, or Beau + Ro. Dewberry says Hampden is especially ideal for visitors since “you can set up a personal shopping experience while in town and they will send you ‘approval boxes’ to try on in the comfort of your home for free!”

While you’re on King Street, make sure to pop into the Juliska’s new flagship store for all your home and entertaining needs (this location also houses their jewelry sister brand, Capucine De Wulf, in case you need an excuse to browse for a sparkly souvenir).

Don’t miss one of our—and Dewberry’s—favorite independent jewelry stores, Croghan’s Jewel Box, which has been a mainstay in Charleston for over a century. There you can find a beautiful assortment of estate jewelry, antique silver and unique stones. To wrap up your day of shopping, walk over to George Gallery for a beautifully curated selection of contemporary and modern art ranging from prints and mixed media to paintings and stoneware.

Friday Evening

charleston, south carolina in the evening
traveler1116 - Getty Images

Head back to the hotel’s “Living Room” after your day of fun and fuel up with some signature house-made popcorn and a delicious cocktail or mocktail. Dewberry says, “We are known for our cocktail called The Panic Button and non-alcoholic Dewberry Spritzer—both are knockouts!”

When you’re ready for dinner, have one of the hotel’s Volvo house cars take you to Vern’s (a buzzy neighborhood restaurant that serves up seasonal American fare). Dewberry says, “The king trumpet mushroom dish is amazing, and you can’t go wrong with the roast spring chicken!

Another great dinner option? Chez Nous, which dishes out delicious French food in a cozy wine bar setting. Dewberry says, “They change their menu each day, and I have never had a meal I didn’t love!”

Saturday Morning

the picnic area of the saturday farmers market on the marion
The Charleston Farmers Market in Marion SquareWolfgang Kaehler - Getty Images

Once you’ve rested, Dewberry recommends heading downstairs to grab a cup of coffee from the lobby. The hotel’s proprietary blend from Second State Coffee, “Morning Dew,” pairs beautifully with a housemade pastry (fair warning: The hardest part of your day might be choosing between a sticky bun, Nutella babka, or sour cream crumb cake).

Just a two-minute walk from the hotel is the Charleston Farmers Market, which runs every Saturday from April to November. Dewberry says, “It's such a fun activity to see and try delicious bites from our local farmers and restaurants. There is sure to be something for everyone!”

There’s more than just fresh produce to be found at the market; you’ll also find artisans and makers selling handmade jewelry, woodwork, woven sweetgrass products, soaps, sculptures, pottery, furniture and more.

Saturday Afternoon

the iconic rainbow row in charleston
Daniela Duncan - Getty Images

Spend the afternoon hunting for antiques at some of Dewberry’s favorite places. She recommends Fritz Porter, Wynsum, and Antiques of South Windermere: “They’re all locally owned with the best treasure hunting and one-of-a-kind finds!”

Fuel up afterwards with a fresh and healthy lunch at Basic Kitchen. Known for their veggie-forward options, even meat lovers will love their nourishing grain bowls, salads and pastas. Dewberry adds, “The cauliflower wings will not disappoint!”

After lunch, walk around and take in all the architectural beauty Charleston has to offer. Some gorgeous spots to add to your must-see list: College of Charleston, Rainbow Row, the Aiken Rhett House, Huguenot Church, and the Riviera Theatre. If you want a bit more structure, you can schedule an architectural walking tour through Viator.

Saturday Evening

the citrus club at the dewberry hotel in charleston
The rooftop of the Citrus Club at The Dewberry HotelThe Dewberry

After a long day of walking, stay close to your hotel room and head upstairs to the Citrus Club. Located on the 8th floor of The Dewberry, it’s considered the tallest rooftop in Charleston.

Dewberry says, “You must get there for the sunset. The views are truly unmatched!” She recommends ordering the crispy piña colada shrimp and the Caribbean rice bowl, followed by the luau pie (made with coffee ice cream, devil's food cake, chocolate sorbet, macadamia nuts, oreos and toasted meringue).

Sunday Morning

south carolina, charleston, south of broad neighborhood, historic residences
A home located in the South of Broad neighborhoodJeff Greenberg - Getty Images

For a luxe and low-key end to your trip, Dewberry says you can arrange experiences such as private sunrise yoga, spa treatments, or a luxury Barton & Gray yacht charter with the hotel’s concierge. You can also book a house car and drive out to the beach for the day (Folly Beach, Sullivan’s Island, and Isle of Palms are all popular spots).

If you’d rather stay local or have a flight to catch, rent a complimentary bicycle from the hotel to get coffee and breakfast at Harken Cafe on Queen Street. From there, ride through South of Broad, the neighborhood where Broad Street intersects the peninsula. The fabulous residential homes and private gardens are not to be missed. Dewberry says, “Our favorite street is Legare.”

If you have time, wander over to The Gibbes Museum of Art. “The building itself is a stunner,” Dewberry says. “And the curation team does such a fantastic job of bringing thought-provoking exhibits.”

After experiencing an itinerary as fun as this one, we promise this won’t be your last weekend in Charleston.

You Might Also Like