Charleston has long been a draw for Bostonians—and vice versa—beginning in colonial times, when one port’s well-heeled headed south to escape their frigid winters and the other’s traveled north to flee their humid summers. Today, the two cities are only a two-hour flight apart, and they still share much in common, including a seaside location, manageable size, a bounty of students and young professionals and an appealing mix of historic and modern neighborhoods. Add in nearby beaches, stellar locavore restaurants, vibrant art and bar scenes and stunning antebellum mansions, and you’ve got a terrific place to visit for a weekend or longer, one deemed the top destination in the U.S. in Travel & Leisure’s World’s Best Awards for the past two years.

Kick off your stay with a carriage ride to learn the landmarks and get a quick overview of Charleston’s history, including how eight former English generals founded it in 1670, thanks to King Charles II, who gave the title of Carolina to the men as a gift for their military service. In honor of the king, the men named the settlement Charles Towne, which rapidly became a wealthy city through the deerskin trade and cultivation of cotton, indigo and rice. You can hear all about it from the drivers of the family-run Palmetto Carriage Works, located near eastern Market Street in a bright red barn.

For lunch, consider nearby Hyman’s Seafood, which Southern Living magazine dubbed the best seafood restaurant in South Carolina (thus explaining the dozens of celebrity-signed plates and photos covering the walls). Order some local shrimp or oysters, the creamy she-crab soup and whatever local fish catches your eye from the dozen or so listed on the chalkboard. A fancier option is Husk, whose chef/owner, Sean Brock, has won national accolades for his upscale southern dishes—glazed pig ear lettuce wraps with marinated vegetables, tomato-smothered shrimp with grits—made with heirloom ingredients and a steadfast commitment to Lowcountry authenticity (you won’t find a drop of olive oil in the kitchen). Then there’s Xiao Bao Biscuit, a cult favorite among locals for its creative Asian soul food. In a casual room with dozens of red chopsticks set in glasses on bare wood tables, you can tuck into dishes like braised lamb over Chinese grits with a poached egg and mustard greens.

Although the beloved Gibbes Museum of Art is currently closed for renovations, the city has dozens of intriguing galleries, including Robert Lange Studios, featuring eclectic works by young artists in a beautiful brick building complete with a piano, a working wooden swing suspended from the ceiling and a residence for visiting artists. Check out more galleries around Church and Meeting Streets, as well as along Broad Street near the Battery and White Point Gardens, located at the tip of the peninsula where the Ashley and Cooper rivers converge into the Atlantic Ocean. Look farther east over the water and you’ll see Fort Sumter, where the first shots of the Civil War were fired in 1861. (A visit is just a half-hour ferry’s ride away.) Walk farther east along the waterfront, and you’ll find the famous pastel-colored homes of Rainbow Row and Waterfront Park.

As for where to lay your head, the hippest spot is the Vendue, an “art hotel” set in seven warehouses dating back to the 1780s. Steps from the water in the French Quarter, this stylish abode houses more than 300 works of art and offers several rotating exhibits per year. Be sure to hit the Rooftop, a bar that’s become the place to see and be seen in Charleston. But if it’s historic luxury you’re looking for, book one of the 21 richly decorated rooms in the Wentworth Mansion, the former Empire-style home of a wealthy cotton magnate and shipper. Expect plenty of Southern hospitality, from the full hot breakfast through afternoon tea, evening wine and hors d’oeuvres, and late-night sherry, port and brandy. And for formal meals, there’s the inn’s restaurant, Circa 1886, set in what was once the estate’s carriage house.

Charleston’s best chow, however, comes from the new crop of rustic, laid-back spots such as the Ordinary, a seafood and oyster hall housed in a former bank. Everything on the small plate menu is scrumptious, whether it’s the smoked oysters in a jar with shallot-parsley vinaigrette, banh mi-style fried oyster sliders on Hawaiian coconut rolls or pickled shrimp with vegetables. FIG also wins raves for its earthy, seasonal fare, like slow-baked grouper with butterbean ratatouille and suckling pig confit with broccoli rabe. Then there is Leon’s, a fried chicken and oyster joint in a former auto body shop, and the Macintosh, home of the bacon happy hour and celebrated for South Carolina specialties such as warm tomato pie and puffy, fluffy bone marrow bread pudding.

Before you leave, don’t forget to stock up on some locally made treasures at the Historic City Market, housed in a Greek Revival Market Hall building completed in 1841. Among the 100 or so booths, you’ll find vendors selling bags of sweet sesame-flecked benne wafers, sacks of grits and hand-woven South Carolina sweetgrass baskets. Then, for a sweet memory of your visit, pop into River Sweets on North Market Street to nab some buttery brown-sugar pecan pralines, best eaten the day they’re made—easily done.

Traveler’s Checks

-If you’re in Charleston on a Saturday, head to the farmers market in Marion Square, where you can fill up on spicy Latin egg dishes, roti and sweet crepes from the food stalls and ogle produce, jewelry and crafts such as hand-stitched dog collars.

-Fuel up with your brew of choice at Kudu Coffee & Craft Beer before exploring the boutiques and antique shops lining nearby King Street.

FIG 232 Meeting St., Charleston (843-805-5900) eatatfig.com

Husk 76 Queen St. (843-577-2500) huskrestaurant.com

Hyman’s Seafood 215 Meeting St. (843-723-6000) hymanseafood.com

Kudu Coffee & Craft Beer 4 Vanderhorst St. (843-853-7186) kuducoffeeandcraftbeer.com

Leon’s 698 King St. (843-531-6500) leonsoystershop.com

The Macintosh 479B King St. (843-789-4299) themacintoshcharleston.com

The Ordinary 544 King St. (843-414-7060) eattheordinary.com

Palmetto Carriage 8 Guignard St. (843-723-8145) palmettocarriage.com

River Street Sweets 100 North Market St. (843-722-1397) riverstreetsweets.com

Robert Lange Studios 2 Queen St. (843-805-8052) robertlangestudios.com

The Vendue 19 Vendue Range (800-845-7900) thevendue.com

Wentworth Mansion 149 Wentworth St. (888-466-1886) wentworthmansion.com

Xiao Bao Biscuit 224 Rutledge Ave. xiaobaobiscuit.com