Courthouse — originally the state capitol building (state), city hall (city), and St. Michael's Episcopal Church (religious). If you head west on Broad you'll pass the John Rutledge House Hotel, with its funky black and white checkered sidewalk, before coming across the ornate brownstone Cathedral of St. John the Baptist.
Old Exchange and Provost
122 E Bay St.
Fun fact — this building used to touch the harbor and served a variety of functions, including being the city's customs house and dungeon. Today, the building (including the dungeon) is a museum. The walls surrounding the city ran down East Bay St., Water St., Meeting St., and Cumberland St., making this area the oldest part of peninsular Charleston.
48 Elizabeth St.
Downtown Charleston is dotted with historic antebellum mansions to tour, but the Aiken Rhett House stands out by focusing on preservation, not conservation. Operated by the Historic Charleston Foundation, the house is the same as it was during the 1800s. No renovations have been made. The urban plantation also has still-intact slave quarters.
70 Cunnington Ave.
Charleston is spoiled with historic cemeteries, but Magnolia is one of the grandest. Sitting on the northern edge of downtown along the marsh, the cemetery features ancient gravestones, tombs, and mausoleums surrounded by grand oaks.
Old Slave Mart Museum
6 Chalmers St.
A major part of the uglier side of Charleston's history, the Old Slave Mart is the only known still-standing former slave market in South Carolina. Built in 1859, the building served as a slave market until the Union occupation of Charleston in 1865. The building also served as a tenement and car dealership before becoming a museum in the 1920s.
79 Cumberland St.
Historic Charleston doesn't get much older than this — completed in 1713, the Powder Magazine is the oldest surviving public building in South Carolina. Originally used to store gunpowder and ammunition, the small building has 32-inch thick walls and is now a small museum.
4 Archdale St.
Created by the Garden Club of Charleston, Gateway Walk is a pedestrian-only path linking several downtown graveyards. The shaded route is perfect for an afternoon stroll, starting at the Unitarian Church graveyard on Archdale, winding past the Charleston Library Society and Gibbes Museum of Art, and finally passing through the Circular Congregational and St. Philip's graveyards.
Old Charleston Jail
21 Magazine St.
The Old Charleston Jail will let you live out your medieval childhood fantasies. Built in 1802, the Romanesque Revival jail housed many famous prisoners, including local slave revolt leader Denmark Vesey and reported female serial killer Lavinia Fisher. Recently, the jail served as the home of the American College of the Building Arts.
329 Meeting St.
Marion Square isn't exactly off the beaten path, but it is still rich with history. It originally served as the Citadel's parade ground, and the military college's original building still borders the square's northern edge. The historic Citadel Square Baptist Church and Emanuel AME are nearby.