The belle of The Palmetto State is more than just a pretty face, thanks to its rich restaurant scene, stellar assortment of museums and art galleries, and host of beautiful beaches. Charleston is a year-round destination with a humid subtropical climate. The best months for a weekend visit are March to May and September to November, when the weather is pleasant, the flowers are blooming and several major festivals are happening.
Carriage tours through historic Charleston
DAY ONE
Most of the historic tours start and finish at Charleston City Market. This beloved spot showcases gifts and souvenirs alongside clothes, hats and footwear from the Charleston Shoe Company, billed as “perfect for cobblestones or cocktails.” The City Market is also home to Hank’s Seafood, locally voted the best seafood restaurant in Charleston for 16 consecutive years. It specializes in comfort food such as rich she-crab soup and buttery shrimp and grits.
Suitably stuffed, wander up King Street, Charleston’s pedestrian-friendly main shopping artery, with its agglomeration of art galleries and antique stores. Highlights include Croghan’s Jewel Box, where you’ll find incredible one-off accessories; Candlefish for its 100-strong candle library; and George C. Birlant & Company, one of the largest antique stores in the South. For art, you’ll find an embarrassment of riches on King Street — led by Robert Lange Studios, Hagan Fine Art and Ben Ham Images. Or keep your wallet in your pocket at the stellar Gibbes Museum of Art. There’s a permanent exhibition focused on the Charleston Renaissance — a period of intense creative cultural revival between 1915 and 1945.
Morning
Charleston is nicknamed “The Holy City” for the scores of spires piercing the heavens from its cobblestoned center. Any visit should begin right here, on the thumb-shaped peninsula at the city’s historic heart, just seven miles long and three miles wide. One of the most popular ways to get your bearings — amid the peninsula’s treasure trove of restaurants, rooftop bars, boutiques and art galleries — is via horse-drawn carriage. There are more than 40,000 such tours a year, with Palmetto Carriage Works and Old South Carriage Company the two main operators, pairing visitors with experienced guides who deftly steer both horses and history-telling (and taking great care of both).
All carriage tours patrol the lower third of Charleston’s peninsula, known as its Historic District — a protected area beginning below Calhoun Street and containing some of the most beautiful Georgian and Greek Revival buildings in North America. Down here amid the winding lanes and convoluted alleyways that have changed little since the 18th century, it’s easy to picture Charleston as an old British port town, which is exactly what it was for the first 110 years of its existence.
Evening
As dusk falls, Charleston’s gas lamps surge into heartwarming life and the taverns and restaurants of the old peninsula start to fill. “Charleston is a drinking city with a history problem,” is the old refrain, and there are plenty of creaky pubs with cozy nooks to choose from. Among the best is McCrady’s Tavern on East Bay Street, where George Washington once ordered a cannon to be fired each time he took a shot, so the city could drink with him. The gunner was busy for most of the night, or so the story goes.
If you don’t fancy a drinking session of presidential proportions, Charleston has an incredible selection of restaurants to choose from, encompassing everything from traditional Southern comfort food and Carolina barbecue to exquisite seafood and impeccable fine dining. One of the hottest epicurean spots in town remains The Ordinary — which is anything but. Housed in a former 1920s bank on King Street, it serves oysters in dozens of delicious ways, with caviar service and a flurry of exquisite fish dishes to follow — not to mention a long and fiendishly inventive list of craft cocktails to wash down the maritime medley.
International African American Museum
DAY TWO
Morning
Start the morning on foot, heading to the bottom of the peninsula to enjoy the glorious views from Charleston’s windswept seafront Battery. Aside from the spellbinding vistas of Charleston Harbor (and Fort Sumter beyond, where the first shots of the American Civil War were fired in 1861), there’s plenty to explore — like Rainbow Row with its famous pastel-hued Georgian townhouses.
Charleston’s history isn’t without controversy. In recent years, the city’s taken an unflinching approach to the darkest chapter of them all — its ties to the slave trade. In 2023, the long-awaited International African American Museum finally opened its doors on Gadsden’s Wharf, where around 260,000 enslaved peoples first arrived in the Americas. The interactive museum is a must-see, deftly handling hard historical truths while also celebrating the African American experience as a whole — from emancipation to the Civil Rights Movement.
Afternoon
Gullah Geechee culture, inherited from those early enslaved West and Central Africans, is still alive and treasured in Charleston today. One of the best ways to experience it first-hand is with lunch at Hannibal’s Kitchen on Blake Street. Favorites at the much-loved soul-food hotspot include fried fish, oxtails and Hoppin’ John — a spicy pea and rice dish.
From seafood to watersports, the harbor is still an integral part of Charlestonian life, and an enjoyable way to interact with it is via one of the city’s unique experiences — “Casual Crabbing with Tia.” Part fishing lesson, part history class, this activity sees larger-than-life local Tia Clark take small groups down to the waterfront to cast baited ring nets and catch blue crabs the old-fashioned way. It’s a relaxing, gleeful way to spend an afternoon by the water — made even more engaging by Tia’s rich storytelling.
When it comes to dinner options, you’ll be spoiled for choice. A winning reservation is always Magnolias on East Bay Street, where the crab cakes (served with red pea succotash and tomato butter) are to die for, and the blue crab bisque is velvety perfection.
Evening
Fully sated, explore Charleston’s legendary rooftop bar scene. Start with the Citrus Club above the Dewberry Hotel. Here, the elegant outdoor terrace is peppered with palms and citrus trees, with views across both of Charleston’s rivers, the Ashley and the Cooper. The clue is in the name here, with orange, lemon and lime-based cocktails the order of the day, and the Orangutan — a salted orange and mint pisco, mixed with Italian Aperitivo and lemon — is a must-try.
Finish the night in style at Fiat Lux, Hotel Bennett’s glamorous ninth-floor cocktail terrace. Here, infused vodkas and gins lead the way, as well-heeled patrons sip concoctions named after famous hotels, while enjoying the spectacular views.
A Southern barbecue plate
DAY THREE
Morning
One of Charleston’s great unsung attractions is its proximity to a garland of golden beaches along the South Carolina coast. Now’s your opportunity to dive in and explore one of the best. The Isle of Palms (known simply as IOP to locals) and Folly Beach both have their fans, and rightly so, but Sullivan’s Island is less busy and more beautiful. Just under 20 minutes’ drive east of downtown, it has everything you could want for a day at the beach, and more.
After a leisurely breakfast, hop in an Uber across the Ravenel Bridge and head straight for the island’s pristine public beach. The golden sands are easily accessible from Station 21 Street, with the gentle Atlantic rollers just beyond.
Afternoon
Once you’ve had your fill of relaxation by the ocean, stroll across to Middle Street where you’ll find several beloved local restaurants within easy walking distance, including High Thyme, Home Team BBQ and Poe’s Tavern (Edgar Allen Poe was famously stationed here during a stint of military service in the 1820s). The pick of the bunch, however, is The Obstinate Daughter — a sunny eatery and patio bar with prompt service, bleached wood furniture and a beachy atmosphere. Don’t miss the perfectly grilled swordfish steaks with capers and currants — or the heavenly pecan bourbon creme brulee, which will live rent-free on the edge of your imagination for many years to come.
Despite the fact this is a tiny island, there’s an abundance of options for the afternoon, especially if you rent a bike from Sealand Adventure Sports. On your to-do list should be the fascinating Edgar Allen Poe Library, where the friendly staff will fill you in on the poet’s short but colorful stay here, and a photo opportunity at historic Sullivan’s Island Lighthouse, otherwise known as ‘Charleston Light’. If you have time and daylight left, it’s worth the extra pedal down the coast to check out Fort Moultrie National Historic Park, where you can experience nearly two centuries of frontline seacoast defense, from 1776 to 1947.
Before leaving, it would be rude not to have a pint at Poe’s Tavern, where the superb local ales are complemented by deliciously crispy fish tacos. Don’t spoil your appetite too much though — one of America’s truly great foodie cities beckons just across the bridge, and you need to finish your visit to South Carolina in style.
Evening
For your final dinner reservation in Charleston, look to combine the best elements of its rich culinary scene in one blockbuster venue. Lowland on George Street — perfectly positioned at the top of the Historic District — is a romantic Southern-style tavern with a roaring fire and an upstairs dining room recognized by the Michelin Guide. Serving hearty modern comfort food, the menu places particular emphasis on this stretch of the Atlantic seaboard (nicknamed the Lowcountry), with all its endemic ingredients and traditional recipes. The fried fish fritters and grilled grouper are both fan favorites, but people drive across state lines for Lowland’s legendary crispy quail, too. And that concludes your weekend in this rich, charismatic, delicious city.
Writer: Jonathan Thompson
