There aren’t many places in the United States that suggest romance more palpably than the jewel of southeastern lowcountry, Charleston. This beautifully preserved bastion of pre-Colonial commerce lies at the confluence of the Ashley and Cooper rivers and is flanked by barrier islands famed for gated golf resorts and swanky condo complexes. Inland, you’ll find some of the most over-the-top plantation homes, many of them now open for tours. But it’s the city’s historic heart, with its palm-shaded lanes and pastel-hued 18th- and 19th-century residences, churches and converted shipping warehouses that provide visitors with the uncanny sensation that they’re strolling through a fairy tale.

What may surprise, either if you’re a first-time visitor or you haven’t been in the past decade or so, is that this rather button-down, traditional city of about 120,000 – the cultural heart of one of the country’s most politically and socially conservative states – has a pronounced gay scene. Since same-sex marriage was legalized statewide in November 2014, the wedding-centric city has also hosted more than its share of gay nuptials and honeymoons.

Perhaps even more surprising is the recent ascent of Charleston (charlestoncvb.com) among the ranks of farm-to-table foodies, craft-beverage aficionados, edgy artists and hipsters. The northern end of downtown, particularly along Upper King Street, contains one of the coolest concentrations of chef-driven, locavore-minded bars and restaurants of any small city in the country. If you’re in town for the weekend, do make a point of visiting the traditional attractions: the opulently decorated house-museums, antebellum churches and prominent military historic sites. But also set aside time to check out the new, independent-spirited side of this dynamic metropolis.

Friday Night

Stick around downtown your first night, supping at one of the dozens of superb restaurants in the central core, many of them set in historic homes. One favorite for both the stunningly prepared modern Southern fare and the gorgeous location inside a glorious 19th-century mansion is Husk (huskrestaurant.com), the domain of James Beard–winning chef Sean Brock. The farm-to-table menu changes often but has included buffalo-style pig’s ear lettuce wraps with spiced peanuts, and slow-cooked heritage pork with red peas, farro and smoky tomatoes.

If it’s late in the evening, and you’re more in the mood for an expertly poured craft cocktail and some lighter snacks, venture into the cozy and hip Gin Joint (theginjoint.com), which serves delish cheese plates and tasty snacks like duck empanadas and hoisin-glazed pork buns. The Card Shark cocktail, with Mata Hari Absinthe, Fernet and smoked honey will warm your soul on a cool evening.

Saturday

Spend the better part of your first full day in town touring the downtown historic district. You might begin with a visit to the Historic Charleston Foundation, which sponsors several renowned events, including late spring’s famed Spoleto Festival, and operates such noteworthy museums as Aiken-Rhett House and the Nathaniel Russell House. From the latter you can stroll to nearby Waterfront Park, with gardens and a promenade overlooking the Ashley and Cooper rivers.

Walk north along Meeting Street, known as Charleston's "Museum Mile," and you'll find one iconic attraction after another. The Charleston Museum, which opened in 1773, is a must, as are the gallery-hopping and shopping along Meeting, King and Bay streets. For a high-octane caffeine pick-me-up, drop by Collective Coffee (collective-coffee.com), a sleek, contemporary café serving single-origin pour-over coffees, along with a good variety of sandwiches, wraps and salads.

As sun falls over Charleston, plan an evening of exploring the city’s emerging restaurant row along Upper King Street. You’ll find some cool touring and tasting opportunities in this part of the city, too, including High Wire Distilling, where you can sample acclaimed spirits, like Silver Rum, Hat Trick Extraordinarily Fine Botanical Gin and Quarter-Acre Sorghum Whiskey. And at the upper end of the neighborhood, two craft breweries are worth a visit, Palmetto Brewing Co. (palmettobrewery.com) and Revelry Brewing Co. (revelrybrewingco.com).

A fun way of approaching the novel food scene on Upper King is by making a progressive meal out of the evening, stopping at a few hot spots, and enjoying an appetizer or two – along with drinks – at each one. Start at Kudu Coffee and Craft Beer (kuducoffeeandcraftbeer.com), which specializes in two of Charleston’s favorite artisan beverages. Then move up King Street to O-Ku Sushi (o-kusushi.com), which serves both inventive sushi rolls as well as sashimi, crudo, green tea soba noodles and other izakaya-inspired treats; and the amusingly named Closed For Business (closed4business.com) “draught emporium,” another top spot for interesting brews as well as decadent snacks, like poutine, beer-battered fish-and-chips and fried pork-cutlet sandwiches.

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At see-and-be-seen Macintosh (themacintoshcharleston.com), sample the exceptional farm-to-table cooking of talented chef Jeremiah Bacon. The artful plates include a salad of fried duck skin with Asian pears and candied-ginger vinaigrette, and sautéed scallops with sunchokes and Brussels sprouts. Located in a landmark bank building, The Ordinary (eattheordinary.com) is a gorgeous space serving beautifully arranged portions of fresh seafood. Consider the Jonah crab toast with lemon and basil, and shad roe with bacon, potato and oyster mushrooms. Right next to High Wire, the Butcher & Bee (butcherandbee.com) is fun both for lunch or late-night (open on Friday and Saturdays only) snacking and drinking. This high-ceilinged space turns out addictively tasty fare from pulled-squash barbecue sandwiches to fried chicken with roasted tomatoes, garlic mayo and dill-verde sauce.

The neighborhood is also home to a pair of popular gay nightspots, the intimate and friendly Dudley's Pub (dudleysonann.com), where you can watch videos, shoot pool and mingle at a conversation-friendly decibel level, and nearby Pantheon (clubpantheon.net), a pulsing dance club open on weekends only. Although not specifically gay establishments, urbane and trendy bars like the retro-cool Belmont (thebelmontcharleston.com) and the endearingly dive-y Recovery Room Tavern (recoveryroomtavern.com) are fun hangouts for kicking off or winding down the evening, and they both draw diverse crowds.

Sunday

Start the day by crossing the modern Arthur Ravenel Jr. Bridge to Mount Pleasant, a suburb just east of the city with a lovely historic district. Enjoy brunch at Charleston’s Cafe (charlestonscafe.com), which is set in a prosaic shopping center but serves anything-but-ordinary morning edibles, including lowcountry shrimp and grits with eggs, and a Southern Benedict with fried-green tomatoes and smoked bacon.

Mount Pleasant is a good jumping off point for exploring Boone Hall, one of the prettiest of the region’s grand plantation museums and gardens, as well as the beaches of Sullivan’s Island and historic Fort Moultrie, which is part of Fort Sumter National Monument. If plantation touring is high on your list of priorities, you might consider an alternate Sunday plan of driving northwest of the city along Hwy. 61 (Ashley River Road), where you can tour such legendary antebellum estates as Ashley Hall, Drayton Hall, Magnolia Plantation, and Middleton Place, which boasts the oldest formal gardens in the nation.

If you’ve spent the afternoon at Boone Hall or Sullivan’s Island, backtrack to downtown Mount Pleasant for a stroll through the relatively new Shem Creek Park, a stunning wetland sanctuary traversed by more than 2,000 feet of boardwalk. Adjacent to the park, Vickery’s (vickerys.com) is an enjoyable place to wrap up your walk. This gay-friendly bar and grill has stunning water views, making it a favorite spot for watching the sunset and sipping a cocktail accompanied by, perhaps, a bowl of Vickery’s signature oyster bisque.

The historic village of Mount Pleasant is also home to one of the most romantic restaurants in the region, the Old Village Post House (mavericksouthernkitchens.com/oldvillageposthouse), which is part of the same illustrious group behind stellar eateries like High Cotton and Slight North of Broad. This handsome old inn also contains six charming, reasonably priced guest rooms. Weekend brunch and nightly dinner are both outstanding here, with dishes like Memphis dry-rubbed, bacon-wrapped pork tenderloin, and salt-and-pepper fried shrimp with smoky-blue sauce.

Where to Stay

One of Charleston’s most playful and interesting accommodations, the Vendue Inn (thevendue.com) occupies a few connected 18th-century warehouse buildings near Waterfront Park and bills itself “Charleston’s Art Hotel” – there’s even an artist-in-residence program. The distinctive rooms feature original, often abstract contemporary works; many have large walk-in showers and gas fireplaces. Be sure to pop up to the sunny Rooftop for a cocktail, and to soak up some of the best views in the city.

The stately mid-19th-century Mills House–A Wyndham Grand Hotel (millshouse.com) is a pink beauty that rises seven stories above the central intersection of Meeting and Queen streets. The classic but contemporary rooms sparkle with Charleston-inspired reproduction antiques and modern perks like 36-inch LCD TVs and ergonomic work desks and chairs; some rooms have balconies, and others have French doors that open to the stunning hotel pool and sundeck. Enjoy breakfast in the sunny Fountain Courtyard of the Barbadoes Room restaurant, which is also a romantic venue for dinner and drinks.

The city has a few gay-owned B&B, including 4 Unity Alley (unitybb.com), a gem hidden down a tiny alley off historic Bay Street. This 18th-century former colonial warehouse contains airy, light-filled rooms with fine antiques. Keep in mind that the four guest rooms here often book up quickly, so it's wise to book well in advance.

Another of the swankiest addresses in town is the romantic Market Pavilion Hotel (marketpavilion.com), which is close to the riverfront and abounds with cushy furnishings and fine artwork. Grill 225 turns out delicious lowcountry steak and seafood. Around the corner, the five-story Harbourview Inn (harbourviewcharleston.com) is a handsome property with soaring ceilings, exposed-brick walls and four-poster beds (many accommodations overlook the Cooper River). The complimentary perks are many: Continental breakfast delivered to your room, afternoon wine and cheese, evening milk and cookies, local walking tours and Wi-Fi.