South of Broad Walk: Waterfront Park (Pineapple Fountain), Rainbow Row & The Battery

The oldest residential quarter of Charleston lies at the southern tip of the peninsula, known to locals as 'South of Broad' (every street south of Broad Street and the 1771 Old Exchange Building). You can see all three of Charleston's classic postcard sights in one flat, 2-kilometre (90-minute) walk from north to south along the Cooper River harbour.

1. Stop 1: Joe Riley Waterfront Park & The Pineapple Fountain

Start at the northern end on Vendue Range, where Waterfront Park opens onto Charleston Harbor:

• The Covered Pier Swings: walk out onto the 120-metre wooden pier shaded by a timber pergola hung with wide wooden family porch swings, watching pelicans, ships and the Charleston Water Taxi against the backdrop of the Ravenel Bridge and USS Yorktown.
• The Pineapple Fountain: tucked beneath a double row of live oaks splashes the 1990 Pineapple Fountain, where wading in the basin is allowed on hot days. In 18th-century Charleston, returning sea captains placed a fresh pineapple on their front gatepost to signal to neighbours that they were home and welcoming guests, making the fruit Charleston's emblem of hospitality.

2. Stop 2: Rainbow Row (79 to 107 East Bay Street) & Stoll's Alley

Walk two blocks south through ballast-stone Longitude Lane to stand opposite 79 to 107 East Bay Street: Rainbow Row, the longest cluster of intact 13 Georgian merchant townhouses (built around 1740 with ground-floor shops and living quarters above) in the United States:

• Why Are They Painted Pastel Colours? After the Civil War, these buildings fell into decay until 1931, when preservationist Dorothy Porcher Legge bought numbers 99 to 101 East Bay Street and painted her facade colonial Caribbean pastel pink. Neighbouring owners followed suit in mint green, yellow, blue and apricot, which also kept brick interiors cooler in the subtropical sun.
• Secret 'Stoll's Alley' (South of 63 East Bay St): a narrow 1.5-metre brick pedestrian gap between the houses leads through a walled corridor of ivy and gas lamps to Church Street.

3. Stop 3: The High Battery Seawall & White Point Garden

Continue south along the 1830s limestone promenade of The Battery past antebellum mansions (like the 1825 Edmonston-Alston House) into shaded White Point Garden, where Civil War cannons sit beneath twisting live oaks facing Fort Sumter.