The 50 Best Places to Live in the U.S. The 10 Most Beautiful Cities to Visit in the United States. The Happiest Cities in the Country—Charleston, South Carolina ticks all the boxes and tops all the usual lists.
However, we would also call it one of the most gentlemanly cities in America, a side of the southern standout that doesn't get as much publicity. On a recent visit to town however, we made sure to document it.
Founded in 1670 and named in honor of King Charles II of England, Charleston blends interesting history, elegant architecture, loads of charm, and great food and drink. It's also home to lots of southern gentlemen and plenty of southern belles—such as Maxim's May/June 2021 cover star Maggie Rawlins—which makes things that much more attractive, and appealing for gents from elsewhere as well.
Here's a photo-heavy tour to get you in the right frame of mind for booking your own visit:
We began by checking into The Restoration, a captivating boutique hotel right off of the most iconic thoroughfare for sampling the best offerings in town, King Street.
Though it's a small property, which keeps things feeling more like a private residence, it has all the amenities of a major luxury hotel. It epitomizes the "New South" with luxurious suites and mixes contemporary style with a dose of local history and some very cool architectural elements.
The library at The Restoration was one of our favorite hangouts, with its marble fireplace, leather chesterfield sofas and amazing collection of Assouline coffee table books on everything from the French Riviera to Art Deco cocktails. Whether you're looking to lounge for a bit or catch up on some work, this is the spot.
Exposed brick, soaring ceilings and oversized windows lend the hotel extra warmth and character, with each space being slightly different, alleviating the cookie cutter effect you can get in even the top luxury hotel chains. Among its features is the The Watch Rooftop Kitchen & Spirits, with an amazing view of some of the city's top landmarks.
One of the best amenities by far is the host of in-room spa services by Amethyst Spa, which means you can get a deep-tissue massage in the comfort of your own suite, and order up refreshments afterwards. You can also refuel at The Rise Coffee Bar on the main floor, which brews up seasonal creations using beans from local roasteries.
The Restoration also boasts a picture-perfect rooftop pool, with alluring views over King Street and the surrounding neighborhood, the ideal spot to relax in the sun with a great craft cocktail from The Watch while you plan your next excursion into town.
And we'd recommend starting with a visit to The Darling Oyster Bar, on King Street off of Morris. Don't let the twee-sounding name fool you—this place has got some world-class seafood that's rivaled only by the quality of the rustic-meets-nautical design. What we really wanted to do was move right in.
As the restaurant notes, in order to enjoy the bounty of the sea on this level, you'd normally have to "drive to Beaufort to crack open a few oysters, score some fresh grouper from Charleston’s barrier islands, or overnight dozens of briny-sweet treats from other parts of the country." But The Darling has it all.
Menu standouts include the Lobster & King Crab Roll, baked oysters with a choice of locally-inspired toppings, and the eye-popping Seafood Plateau, which lets you sample all of the very freshest oceanic arrivals. To go along with it there is a great selection of local beer on tap as well as a well-curated wine and cocktail list.
When you're ready to get out on the water yourself, book in with Charleston Harbor Tours. Weather permitting, a sailboat cruise is the most gentlemanly way to explore. CHT has Charleston’s only three-masted tall ship, the 84-ft. schooner Pride, which is available for an afternoon dolphin sail, a two-hour sunset sail—beer and wine is available for purchase—and an adults-only full moon sail.
If being by the water is a priority—and Charleston is known for its waterfront attractions on Charleston Harbor, an inlet of the Atlantic Ocean—as well as comfort and style, then we'd highly recommend a stay at the newly renovated, and aptly named, HarbourView Inn.
The elegant southern vibe offers the feel of a private manor house yet is adjacent to major downtown Charleston destinations like The Battery and Waterfront Park.
The hotel is housed in a former 1930s indigo cotton warehouse, hence the incredible amount of character. HarbourView Inn was the first waterfront hotel in Charleston's Historic District and remains the leader of the pack, especially with the $1 million interior refresh by notable South Carolina-based interior designer, Jenny Keenan.
Some rooms and suites have fireplaces and balconies, and beautiful views are par for the course, as are evocative architecture details in some rooms that connect you with the building's history.
That's in addition to other luxe touches like custom furniture and upholstery, plush carpets from Fine Rugs of Charleston, and original work from local artists, with unique pieces dedicated to each room.
The property refresh also includes a refurbishment of HarbourView Inn’s highly-popular rooftop terrace, which is the only remaining private rooftop in the Historic District. There you'll find new custom outdoor furniture, and guests can take part in a complimentary wine and cheese hour every day. Just the thing to tide you over until your next culinary foray.
Which brings us to Husk. One of Charleston's most famous restaurants, and justly so, Husk (which also now has outposts in Savannah and Nashville as well) recently celebrated its 10th anniversary, and continues to rack up awards, adding to the 2010 Best Chef of the Southeast honors it initially scored from the James Beard Foundation.
These days Lowcountry native Travis Grimes reigns as Executive Chef, and he nightly "reinterprets the bounty of the surrounding area, exploring an ingredient-driven cuisine that begins in the rediscovery of heirloom products and redefines what it means to cook and eat in the South."
For a more casual dining experience, as well as direct access to Husk's incredible whiskey collection, we recommend dining in the historic brick building that houses the bar.
When a new day dawns, it's high time to go for a drive. And check out some of the extremely cool custom Land Rover Defenders built by Arkonik. In 2020, the UK-based brand opened Special Vehicle Operations (SVO), its new U.S. HQ in Charleston catering to those well off—and wise—enough to commission one of its bespoke creations. If you seem like you mean business, you can talk to them about test driving one of their mean machines.
If you don't have a proper southern gentleman's wardrobe of your own, this is the time to visit storied King Street clothier Ben Silver. A tribute to classic style, this British-influenced shop (currently open by appointment) has a beautiful array of sports and dress threads that will have you looking right at home amongst Charleston's landed gentry. Even better, it's right across the street from the city's oldest, and best, wine bar, Bin 152.
Hungry again? We thought as much. So we'll round out with a few eclectic options, starting with the stunning Leon's Poultry & Oyster Shop. Leon's specializes in fried chicken, raw oysters, soft serve, great beer, rosé on tap, frozen G&T’s, grower champagne—the connoisseur's pairing with fried chicken—and more, all in a super-cool old garage that's been refurbished and now has a wood-burning fireplace and a collection of vintage nautical art.
Leon's is in an up-and-coming part of Downtown Charleston that's quickly becoming known for its amazing bars, restaurants, and cool industrial conversions. So you might want to plan to visit a few other spots like Graft Wine Shop & Wine Bar, and Maison, while you're at it.
If it's healthier fare you're after, head to Basic Kitchen, conveniently located right across the street from The Restoration. A standout for lunch or dinner, the focus is on seasonal, local produce and the best available ingredients, and diverse flavors inspired by dishes from around the world. Along with the wild-caught seafood and sustainably-raised meat, there's a kickass cocktail menu that also features organic flourishes.
Speaking of cocktails, the perfect place to wind up our tour is on the roof of The Dewberry hotel, at the Citrus Club. Its seats are some of the most coveted in town, thanks to the excellent menu of drinks and snacks and views that stretch for miles in all directions—it's Charleston's highest, and hippest, rooftop bar.
Citrus Club is also one of the most stylish, photo-worthy venues in Charleston, but it doesn't feel too designer-y. Kick back with a killer cocktail like the Long Time Listener, made with Fortaleza reposado tequila, St. Germain, dry curaçao, lemon syrup, lemon juice, and Peychaud’s Bitters (a nod to the South's cocktail heritage).
And you won't go hungry either, with treats like the Dewberry Burger, with onions bordelaise, Emmenthal cheese, and vegetable slaw on a seeded potato bun; and crispy Piña Colada Shrimp with an addictive sweet and sour sauce that serves as the perfect counterpoint to the bartender's concoctions. Bottoms up.