The ultimate weekend in Charleston

Charleston enchants visitors with its vibrant architecture, cobblestone streets, and a rich history that weaves through the Civil War and the Civil Rights movement. In just one block, you can stroll along a historic path, explore a trendy boutique, marvel at centuries-old homes, and savor a wealth of culinary delights—try the dressed-up biscuits at Callie’s and the luscious she-crab soup at 82 Queen, both of which are personal favorites.

As a Virginia native and a resident of South Florida, I’ve cherished the charming, steeple-filled “Holy City” for decades. I've spent weekends enjoying the leaping dog competitions at SEWE (the Southeastern Wildlife Exposition, for those new to Charleston), but most often, I simply love to wander and be amazed by the friendly locals and beautifully preserved estates that always prompt a search for their historical significance.

• When to arrive: For the perfect long weekend, aim for a Friday arrival. If possible, extending your stay from Thursday to Sunday is even better. Charleston’s peak seasons are from March to May and September to November, when the weather is delightful and festivals abound.
• How to get from the airport: Charleston International Airport is just a 20-minute ride via Uber or Lyft to downtown. Budget options include CARTA (Charleston’s bus service) and hotel shuttles, although their schedules can be unpredictable. Taking a taxi is the most straightforward choice.
• Getting around town: The best way to experience Charleston is by taking your time. CARTA offers a free bus service, DASH, with three routes covering popular tourist spots like the College of Charleston, King Street, and City Market. For those wanting to explore further, there are numerous routes to the outskirts. If a beach day at Folly Beach sounds appealing, renting a car is advisable for easier packing and because rideshares can be hard to find on the beach.
• What to pack: Bright colors and fun patterns are always in style in Charleston. Comfortable walking shoes are essential for tackling the occasionally uneven streets. Lightweight attire is a must during the summer to handle the heat and humidity.

Friday

Morning

Drop off your bags at the hotel and make your way to Second State Coffee on Beaufain Street for your morning boost. Housed in a historic building, this coffee roaster is a local favorite with a minimalist atmosphere—sunlight streams through large windows, and black-and-white family photos adorn the walls. Treat yourself to a pour-over made from high-quality beans. Once you're energized, head over to the French Quarter and wander through the 19th-century City Market, where locals and visitors alike browse local art, taste jellies, and shop for candles, jewelry, and a variety of charming trinkets.

How to spend the day

Spend your Friday afternoon in the southern part of town, mainly around the French Quarter and Lower King Street. Visit the Gibbes Museum of Art, which features rotating exhibitions alongside a permanent collection showcasing life in the American South from the colonial period to today. Just half a block east, tour the Thomas Elfe House, Charleston's oldest restored historical home, dating back to 1760. When hunger strikes, Poogan’s Porch is a beloved spot for Southern cuisine and is conveniently located less than a block from the house.

Dinner

At Oak Steakhouse, you'll find succulent steak cuts complemented by tempting seafood dishes, including Oysters Rockefeller drizzled with bacon fat and topped with hollandaise sauce. Reservations are a must, as it’s a popular weekend destination. Alternatively, check out Brasserie La Banque, also on Broad Street, set in a beautifully renovated historic bank offering exquisite French-inspired dishes.

After dark

Catch a performance at Dock Street Theatre, the first theater ever built in the US. They frequently feature classics like “Fiddler on the Roof” and “Legally Blonde.” Wrap up your evening with a nightcap at The Gin Joint, where you can try the “Bartender’s Choice” – just give them two adjectives, and they’ll craft a drink tailored to your descriptions.

Saturday

Morning

You’ve earned a biscuit by now! For the finest in town, visit Callie’s Hot Little Biscuit on King Street, a beloved breakfast spot. The line may be long, but once you taste a pimento-infused biscuit, you’ll understand why. Pro tip: it opens at 8 am daily, so try to arrive early to beat the College of Charleston crowd for a shorter wait. Afterward, stroll a few blocks south to Marion Square, where the town’s farmer’s market operates every Saturday from 8 am to 2 pm, featuring fresh South Carolina peaches, pecans, baked goods, and bohemian jewelry.

How to spend the day

The boutiques on King Street can keep you occupied for hours. Sewing Down South, inspired by Bravo’s Southern Charm star Craig Conover, offers a unique selection of colorful furniture, clothing, kitchen items, and more. Las Olas, located nearby on Upper King Street, is an urban swimwear shop showcasing trendy prints from brands like Duvin and Bond-Eye. For upscale shopping, Charleston Place is an indoor paradise featuring stores like Gucci, Louis Vuitton, and Tommy Bahama. When you need a break from shopping, head to Brown Dog Deli, just four blocks west of King Street, known for its 80s decor and the Super Smash Bros Burger, a gourmet take on the Big Mac.

Dinner

The Ordinary is known as an oyster hall, serving a wide array of oysters along with shrimp sourced from South Carolina, stone crab claws, and various other fresh seafood delights. Be sure to make a reservation, or if you're in a hurry, the patio and bar areas offer first-come, first-served seating. If seafood isn't your thing, head two blocks southeast to Sorghum & Salt, which features four- and six-course tasting menus crafted from locally sourced ingredients.

After dark

For a thrilling finish to your Saturday, consider a ghost tour. Bulldog Tours presents several site-specific tours that explore Magnolia Cemetery, Charleston Harbor, and the USS Yorktown, which is permanently docked along the city’s waterfront. If you’re a true crime aficionado, their Haunted Jail Tour takes you through the Old City Jail, notorious for housing some of Charleston's most infamous criminals and reputedly one of the city's most haunted sites. Alternatively, Ghost City Tours offers a haunted pub crawl that pairs ghost stories with visits to local bars, adding an entertaining twist to your evening.

Sunday

Morning

Let’s not dwell on the fact that it’s your last day! Instead, make your way to Mercantile and Mash on East Bay Street and order their enormous avocado toast topped with marinated cherry tomatoes and everything seasoning. You’ve probably spotted the triangular-arched Arthur Ravenel Jr. Bridge in the distance – if you’re feeling adventurous, it’s a 2.5-mile trek each way with a pedestrian path. You’ll be treated to stunning views of the Charleston skyline, and once across the bridge, you can explore the USS Yorktown, home to vintage jets.

How to spend the day

After your bridge adventure, reward yourself with a meal from a Charleston barbecue legend. Rodney Scott’s BBQ – back on the east side – boasts a slew of awards and is known for its sides like tangy collard greens and crispy hush puppies, just as much as its expertly smoked meats. Once you’ve refueled, dive into Charleston's vibrant brewery scene on the north side. Start your brewery tour at Palmetto Brewing, where you can catch live music in the courtyard. Next, head to Revelry Brewing, a half-mile north, which features a rooftop with open-air vibes. Finally, make a quick 5-minute Uber trip to Edmund’s Oast, complete with a large courtyard, yard games, and a diverse tap list inspired by everything from cereal to apple cider donuts.

Dinner

By now, you’ve discovered that Charleston is a culinary paradise, so hopefully you’ve saved room for dinner. Head over to The Grocery, a beloved establishment by Kevin and Susan Johnson that’s been delighting locals since 2011. Here, you’ll find a menu of New Southern cuisine featuring tapas-style dishes, perfect for sharing. Don’t miss the roasted peaches, adorned with pecan granola and goat cheese. As Sunday evenings tend to be more relaxed in the Holy City, enjoy a leisurely stroll back to your hotel, perhaps starting to dream about your next getaway to Charleston.