Road Trip: Charleston, South Carolina – The Old South Charmer

From the end of the American Revolution until South Carolina’s succession from the Union in 1860, the South operated almost autonomously within the greater United States, pioneering the distinctive fashion, culture, etiquette, architecture and lifestyle now referred to as quintessentially “Southern.” Though heavily destroyed during the Civil War, the spirit of the South’s cultural and social capital, Charleston, never surrendered. And while the hoop dresses and bayonets have long disappeared, Charleston honors both the glory and pain of its historic past while adapting to modern times like a gracious Southern belle.

Charleston, South Carolina - road trip to the SOuthern hub

Miles from Naples: 590


Why Go: Charleston is one of America’s most charming and historic cities, flaunting a surprisingly liberal edge. The city center buzzes with college students, foodies, tourists and families traversing the quaint and colorful streets of Rainbow Row, the tranquil waterfront and the residential alleys wrapped in grand live oaks and Spanish moss. Beyond Downtown’s borders, greater Charleston revels in the beautiful beaches, historic monuments and plantation homes that define its Southern beauty.

Carriage Tour of Charleston, South Carolina - Historic stop on the Southern Road Trip


Try This: Meeting Street is downtown Charleston’s principal thoroughfare, where romantic carriage tours and fascinating ghost tours recount the city’s sordid and splendid past while sweetgrass basket weavers construct bespoke souvenirs from the Low Country. Museum Mile teems with cultural heritage and senior docents, eager to disclose the many stories of Charleston’s antebellum homes and historic places of worship.

Road Trip to America's South - Charleston, South Carolina - historic downtown - Antebellum Homes


Where to Sleep: Belmond Charleston Place is the city’s premier hotel, blending eighteenth-century style with modern elegance. The hotel’s iconic chandelier sways between two grand staircases (pictured below), leading to suites and rooms that continue the antebellum fairy tale. The glass-enclosed rooftop pool and award-winning spa reign as the city’s superlative retreats.

Belmond Charleston Place - two grand staircases - iconic hotel in Charleston, South Carolina

   The family-friendly Wild Dunes Resort occupies the entirety of Charleston’s Isle of Palms, with plentiful green space and beachfront peppered by two hotels, vacation rentals and condominiums. Resort-style amenities abound, including six dining outlets and oceanfront pools at the community’s Grand Pavilion, a great place for the kids to socialize. The Tom Fazio-designed Links Golf Course (pictured below) is one of Fazio’s personal favorites among the hundreds he’s designed globally.

Tom Fazio-designed Links Golf Course - Wild Dunes Resort


For Foodies: The Charleston Grill, a AAA Four-Diamond restaurant and the Mobile Four-Star award winner, presents a seasonally inspired menu of “Pure, Lush, Southern” and “Cosmopolitan” dishes complemented by one of the nation’s best wine lists. Or, for a funky night out, head to Sullivan Island for the eclectic Poe’s Tavern. The bustling eatery serves farm-to-table bar food in a kitsch setting that pays homage to Edgar Allan Poe, who served at Fort Moultrie between 1827 and 1828.

Charleston Grill - Foodie Spots in Charleston, South Carolina - Must Stop Eats


Boone Hall Plantation and Gardens - historic must-sees in Charleston, South Carolina

Top Attractions: Boone Hall Plantation and Gardens (above) is one of the nation’s oldest working plantations, open for tours of its original slave cabins, the colonial revival plantation house and antebellum structures. Out on Sullivan Island, the restored armaments at Fort Moultrie reveal a living chronicle of American seacoast defense (armaments pictured below), beginning with the American Revolution and ending with World War II. Moultrie’s cannons peer over desolate beaches, perfect for long, barefoot walks that end in the far reaches of the island.

Fort Moultrie - Historic Must-Sees in Charleston, South Carolina

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