On a Whim

The peninsula is a preservationist’s muse with Charleston’s chronology and curious customs at every turn.

Doors encircled by rope molding, tabby quoins, earthquake bolts, and ornate ironwork festoon the handsome dwellings that populate the South of Broad neighborhoods. Carolopolis Award plaques, copper lanterns, and hitching posts hint at a bygone era. Manicured public parks and glimmers of private gardens make for a botanical wonderland, where the delicate aromas of tea olives and Carolina Jessamine dance amid the seabreezes. The harmony of church bells resonates with the hum of the city, which is rooted in the solemnity of ancient graveyards.

These are the details that reveal themselves when the peninsula is explored on foot.

Innately walkable, the city’s gridlike east-west streets stretch from shore to shore. Bookended by two rivers, which—it is said—converge to form the Atlantic Ocean, the peninsula is hemmed in by water and sky. Stroll along sidewalks and seawalls. Let the human scale of the peninsula enfold you in a state of Old World enchantment.

With smart phone in tow, set out for a day of visual discovery through downtown Charleston. Scroll down to discover some suggested stops along the way. And tag your photos #Charlestonly when sharing via Instagram!

On a Whim Instagram


1. We love the almond milk lattes and courtyard vibe at Kudu, where the friendly baristas always remember our names and favorite beverages. Perfect place to start a day of exploration.

Head down King Street toward the start of The Gateway Walk, a lovely three-block stroll that starts on Archdale Street amid the steeples of St. John’s and the Unitarian Church and wends its way to St. Philip’s Church on Church Street. Look for plaques along the way:

Through hand wrought gates
alluring paths lead on to pleasant places,
where ghosts of long forgotten things
have left elusive traces.

Travel south on Church Street to the White Point Gardens Pavilion, a small, gazebo-like bandstand that sits nestled beneath a canopy of live oak trees. Get a close up view of the cypress slat and cast iron Charleston Battery Benches to discover native flora and fauna molded into the armrests.

Along the way, keep a look out for the city’s beguiling historic alleys. Larger than a footpath but too narrow to accommodate today’s oversized vehicles, the following places are some of our favorite intimate places: Stoll’s Alley, Bedon’s Alley, ZigZag Alley, Longitude Lane, Philadelphia Alley, Ropemaker’s Lane, and Price’s Alley.

While wandering, look up! Notice the earthquake bolts, a fashionable invention that appeared in the aftermath of Charleston’s earthquake of 1886. Intended to gird dwellings with iron rods, the bolts are perhaps little more than ornamentation and appear in a variety of shapes, including lion heads, stars, circular plates, and rectangular bars. 

Stop for lunch at Fleet Landing, a 1940s naval building-turned-seafood restaurant with sweeping views of the Charleston harbor. After lunch, walk one block over to see the grand façade of the United States Custom House.

Wind down your day with a visit to the Charleston City Market, one of the oldest public markets in America. Take special note of the several dozen people weaving baskets. Made to winnow rice on plantations, Gullah sweetgrass baskets are one of the oldest handcrafts of African origin in the United States. See the baskets come to life, and kindly ask permission before taking photographs of the basketmakers.

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