Charleston, South Carolina was once the wealthiest and most populous of all 13 original colonies, for reasons that wouldn’t exactly make you proud.
Known as the "Holy City" for its sea of steeples, the city offers a stunning blend of pastel-colored "photo eye candy" homes and profound historical truths.
Today it is one of America’s most walkable, most photogenic, and most historically layered cities. A single afternoon on its streets will take you from Revolutionary War landmarks to some of the most vibrant architecture on the Eastern Seaboard — and if you’re paying attention, it will also bring you face to face with the history of slavery that built much of what you’re looking at. (That’s why Charleston was the richest and most populous in 1776.)
This itinerary follows the same path we walked for our Photowalks episode — combining the best photo spots, local food, guided history, and practical tips for capturing it all on your phone.
Start with a Guide
If you want a deeper read on the history, consider beginning with a guided tour before your self-guided walk. Local companies like Bulldog Tours have been leading walks through the historic district for over 25 years — guides know not just the facts but the stories. (We walked with Bulldog founder John LaVerne, as you’ll see in the accompanying video. I can’t recommend him more highly.)
Start at the City Market & Church Street
Now that you know your way around, follow this route, walk slowly and take it all in with your phone camera.
City Market/Rainbow Row/Battery/Preservation Society/International; African-American Museum
Begin at the City Market and then head south down Church Street — widely considered one of the best-preserved streets in the country. This is Charleston’s longest cobblestone corridor, and those stones have a story: they were used as ballast in the bottoms of ships sailing from Europe and dumped onto the docks when no longer needed, eventually becoming the street surface you’re walking on today.
The buildings lining these streets date back to the 1700s and 1800s, many still lived in by Charleston families. The city’s preservation movement has kept them intact, and the result is something rare in America — a genuine living museum.
Throughout the historic district, you’ll find artisans selling handwoven sweetgrass baskets — a Gullah Geechee tradition with roots in West Africa, and the best souvenir you can bring home from Charleston. A single basket can take 8+ hours to make by hand. They are not cheap, and they shouldn’t be.
Charleston also has a thriving community of local makers. Look for Brackish (feather jewelry sold internationally) and Smithy Cast Iron (considered among the best cast iron and carbon steel cookware made in America, confirmed by America’s Test Kitchen).
The Four Corners of Law
At the intersection of Meeting and Broad Streets, you’ll find what locals call the Four Corners of Law — reportedly the only intersection in America where every form of law governing mankind is represented at once. The federal courthouse covers federal law, the county courthouse handles county law, City Hall represents city law, and St. Michael’s Episcopal Church — one of Charleston’s most beautiful landmarks — stands in for divine law.
St. Michael’s, built in 1761, is also the final resting place of two signers of the Constitution. George Washington worshipped here during his 1791 Southern Tour — the longest stay any president has ever made in Charleston.
Rainbow Row
Rainbow Row on East Bay Street is Charleston’s most photographed landmark — a stretch of 13 Georgian row houses painted in candy-bright pastels along East Bay Street. Most of these buildings date to the 1700s. The colorful tradition began in the 1950s when a local woman bought one of the then-crumbling tenement houses, renovated it, and began painting the façades in vivid hues to bring life back to the street. The movement caught on, and Rainbow Row was born.
The Battery & Charleston Harbor
Continue from Rainbow Row south to the Battery, the promenade at the tip of the Charleston peninsula where the Ashley and Cooper Rivers meet and flow into the Atlantic. The antebellum mansions along East Battery were built in the early 1800s as springtime retreats for plantation owners. They are among the most photographed homes in the South.
Out in the harbor, you can see Fort Sumter — the island fortification where Confederate forces fired on Union troops on April 12, 1861, marking the start of the Civil War. South Carolina was the first state to secede from the Union, in direct response to shifting federal policies on slavery.
By the way, those aren’t palm trees lining the Battery — they’re palmetto trees, the state tree of South Carolina, and a cousin to the palm. Look for them on everything from signage to the state flag.
The International African American Museum
This is the most important stop on the itinerary — and arguably the most important building in Charleston.
Charleston was the largest port of entry for enslaved Africans in all of North America. Of the 6% of enslaved people brought from Africa to North America (the rest went to the Caribbean and South America), fully half came through Charleston alone. More enslaved people were sold here than in any other American city, with auction houses operating along the wharves and throughout downtown. The largest single slave auction in American history took place just north of the Old Exchange Building, where over 630 people were sold in a single day.
The International African American Museum sits on Gadsden’s Wharf — the very waterfront where tens of thousands of enslaved Africans were forced to arrive. It documents the full arc of that history, from the trans-Atlantic slave trade through the Civil War, into civil rights and the present day. It is an honest, frank, and essential visit.
Also worth visiting nearby: the Old Slave Mart Museum, housed in the actual auction gallery building from the 1850s — the only surviving slave auction structure left in South Carolina.
Food & Drink
What to Eat in Charleston
Lowcountry cuisine is one of America’s great regional food traditions — and its origins are inseparable from the history of enslaved Africans in South Carolina. Enslaved cooks combined ingredients and techniques from West Africa with Native American foods, and the recipes of British, French Huguenot, Scottish, and Irish settlers to create what we now call Lowcountry cooking. The credit, as local historians note, belongs to them.
What to look for on menus:
Shrimp and grits — the quintessential Charleston dish. Chances are the shrimp was in the water that morning.
She-crab soup — a rich, creamy bisque unique to the Lowcountry.
Fresh local seafood — with the Atlantic, Ashley River, and Cooper River all nearby, produce turnover is remarkable.
Contemporary Southern — restaurants like The Peacock blend American cooking with international influences while drawing on Lowcountry traditions for seasonal specials.
Where to Stay
Set up base just across the bridge in Mount Pleasant. It’s quieter, more affordable, and gives you easy access to both downtown and the coast. We stayed at the Best Western Patriots Point (and yes, Best Western sponsors Photowalks.)
From here, you’re minutes from:
Patriots Point (naval museum + harbor views)
The best vantage point of the Arthur Ravenel Jr. Bridge
Quick drive into the historic district
📱 My Pro Photo Tips: Capturing Rainbow Row
Since I shoot my entire show on a phone, here is how to make those famous colored houses pop:
Cross the Street: Don’t stand directly in front of the houses. Cross over to the opposite sidewalk to get the full “rainbow” perspective.
Go Early: Be there at sunrise. You’ll get soft, even light and—most importantly—no tourists blocking your shot.
The “Compression” Trick: Instead of using your standard wide lens (1x), walk further away and use your telephoto lens (3x or 5x). This “compresses” the houses, making the colors look tighter and more vibrant.
Work the Angles: Don’t just shoot head-on. Stand at a 45-degree angle to the row to create depth and leading lines.
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