Charleston captivates visitors with its colorful architecture, cobblestone streets and rich tapestry of history spanning the Civil War and the Civil Rights movement. Within a single block, visitors can wander a historic pathway, peruse a modern boutique, gawk at a centuries-old abode and enjoy seemingly endless creative culinary finds – dressed-up biscuits at Callie’s and the creamiest she crab soup at 82 Queen are personal favorites.
As a Virginia native and South Florida resident, the steeple-clad, ever-friendly “Holy City” has been a favorite destination of mine for decades. I’ve made weekends out of watching leaping dog competitions at SEWE (the Southeastern Wildlife Exposition, for Charleston newbies) but, most commonly, I simply like to wander around and be ever dazzled by the most amicable locals and preserved estates that are instantly worth a “what in the world is the significance of this place?” search.
- When to arrive: Come on a Friday for a true long weekend. If you can swing a Thursday through Sunday stay, even better. Charleston’s high seasons are March to May and September to November when the weather is mild and festivals are plenty.
- How to get from the airport: Charleston International Airport is a 20-minute Uber or Lyft to the heart of downtown. Budget-friendly options include CARTA (Charleston’s bus service) and hotel shuttles, but they can have varying and sometimes difficult-to-pin-down schedules. A taxi is the easiest option available.
- Getting around town: Charleston is best experienced via a slow saunter. CARTA has a free bus service, DASH, with three different routes serving popular tourist areas like the College of Charleston, King Street, City Market and more. If you want to go further afield, there are more than a dozen routes serving Charleston’s outskirts. Fancy a day of soaking up the rays on Folly Beach? Renting a car is the best option for ease of packing and also because rideshares on the beach are typically scarce.
- What to pack: Bright colors and patterns are a year-round norm in Charleston. Always pack comfortable and reliable walking shoes for navigating the sometimes uneven urban terrains. Lightweight clothing is a necessity in the summer to combat the heat and humidity.
Friday
Morning
Unload your bags at your hotel and head to Second State Coffee on Beaufain Street to fuel up for the day ahead. Nestled in a heritage building, this is Charleston’s go-to coffee roaster with a simplistic vibe – natural light floods in through the large windows and black-and-white family photos are dotted around the room. Order a pour over made from top-tier beans. Once buzzed, zip over to the French Quarter and stroll through the 19th-century City Market. It’s where locals and tourists peruse local art, sample local jellies and shop for candles, jewelry and seemingly any trinket in between.
How to spend the day
The south side of town is where you should spend your Friday afternoon, generally encompassing the French Quarter and Lower King Street. Peruse the Gibbes Museum of Art, which, in addition to rotating exhibits, has a permanent collection depicting life in the American South spanning the colonial era to the present day. A half block east, take a tour of the Thomas Elfe House, the oldest restored historical house in town, dating back to 1760. When hunger calls, Poogan’s Porch is a city-wide favorite for Southern fare and is less than a block east from the house.
Dinner
Oak Steakhouse has tender cuts of steak with equally delightful seafood offerings, including an Oysters Rockefeller drizzled with bacon fat and topped with hollandaise sauce. Making a reservation is essential as it’s the place to be on weekends. Another option is Brasserie La Banque, also on Broad Street – it’s housed in a beautifully updated historic bank with meticulous French-inspired fare.
After dark
Catch a show at Dock Street Theatre, the first structure in the US built for theater. It regularly showcases classics like “Fiddler on the Roof” and “Legally Blonde.” End the evening with a nightcap at The Gin Joint and go for the “Bartender’s Choice” – you pick two adjectives, and the bartender will whip together a drink based on them.
Saturday
Morning
Okay, you’ve earned a biscuit by now. For the best in town, head to Callie’s Hot Little Biscuit on King Street, a local favorite spot to grab breakfast. Sure, there may be a lengthy line, but take one bite of a pimento-doused morsel and you’ll get it. Pro-tip: it opens at 8am daily and if you can get there early and beat the College of Charleston rush, you’ll have less of a wait. From here, stroll a few blocks south to Marion Square, which hosts the town’s farmer’s market every Saturday from 8am to 2pm. The freshest of South Carolina peaches, pecans, baked goods and bohemian jewelry are standard fare.
How to spend the day
The boutiques along King Street could keep you entertained for days. Sewing Down South is a uniquely Charleston experience – it's the brainchild of Bravo Southern Charm star Craig Conover and features colorful furniture, apparel, kitchen utensils and the in-between. Las Olas, also right there on Upper King Street, is an urban swimwear shop, featuring trendy prints from the likes of Duvin and Bond-Eye. For upscale perusing, Charleston Place is an indoor utopia with outposts from Gucci, Louis Vuitton, Tommy Bahama and a couple of dozen others. For a reprieve from all the shopping, Brown Dog Deli is nestled four blocks west of King Street. It has 80s decor and a Super Smash Bros Burger – a totally elevated version of a Big Mac.
Dinner
The Ordinary is billed as an oyster hall and it has plenty of ‘em as well as South Carolina–sourced shrimp, stone crab claws and many other fresh seafood options. Snag a reservation or, if you’re on the fly, the patio and bar areas have first-come, first-served seating. If seafood isn’t your jam, Sorghum & Salt is two blocks southeast and has four- and six-course tasting menus using locally sourced ingredients.
After dark
If you're up for a spine-tingling experience, end your Saturday with a ghost tour. Bulldog Tours offers several site-specific tours to Magnolia Cemetery, Charleston Harbor and the permanently docked USS Yorktown on the city’s shores. True crime junkies might consider their Haunted Jail Tour, which takes you through the Old City Jail, known for housing some of Charleston's most notorious criminals and rumored to be one of the city's most haunted buildings. Alternatively, Ghost City Tours's offers a haunted pub crawl that combines ghost stories with visits to local bars, adding a spirited twist to your evening.
Sunday
Morning
Let’s not think about how it’s already your last day, okay? Instead, head to Mercantile and Mash on East Bay Street – order the mammoth avocado toast which is layered with marinated cherry tomatoes and everything seasoning. By now you’ve likely seen the triangular-arched Arthur Ravenel Jr. Bridge looming in the distance – if you’re up for stretching your legs, it’s 2.5 miles each way and has an open walking path. You'll enjoy unparalleled vistas of the Charleston skyline and, across the bridge, you can tour the USS Yorktown, which has old jets on board.
How to spend the day
Post-bridge stroll, you’ve earned a treat from a Charleston barbecue icon. Rodney Scott’s BBQ – back on the east side of the bridge – has won every award in town and beyond, and its sides – like tangy collard greens and ultra-crispy hush puppies – are equally as celebrated as its pit-cooked meats. Once re-energized, it's time to hit Charleston's killer brewery scene on the north side of town. Begin a brewery hop at nearby Palmetto Brewing, which has regular live music in its courtyard. Bounce to Revelry Brewing, a half-mile north, with open-air rooftop vibes. Edmund’s Oast – a quick 5-minute Uber north – is your final stop with a massive courtyard with yard games, plus a tap list of beers inspired by everything from cereal to apple cider donuts.
Dinner
By now you’ve learned that Charleston is foodie heaven and hopefully, you’ve saved some room for dinner. Step into The Grocery, the creation of Kevin and Susan Johnson that’s been a local staple since 2011. New Southern cuisine is the fare, with tapas-style offerings, so be ready to share. Order the roasted peaches, topped with pecan granola and goat cheese. As Sunday evenings are comparatively quiet in the Holy City, take a leisurely stroll back to your hotel and perhaps start planning your next weekend in Charleston.
