Whether or not it wins the crown, it is absolutely packed with history, walkable streets, and camera‑ready scenes at every turn, making it a fantastic 2 or 3 day getaway.

Day 1 – Historic Core, Castillo & Gilded Age Glamor

Start where St. Augustine began: the historic core, laid out by the Spanish in the 1500s. Wander Avilés Street, considered the oldest street in the United States, and let yourself get lost among cobblestones, side alleys, and a surprising variety of architectural eras.

Then drift over to St. George Street, a pedestrian corridor lined with shops, cafés, and historic facades. Give yourself time to duck into the “nooks and crannies” just off the main drag—these side streets are where you’ll find some of the city’s most intriguing doorways, balconies, and quiet courtyards that are perfect for photos.

Tip: Treat this as a walking town and leave the car parked; parking is limited, and you’ll see more on foot than you ever will circling for a spot.

Late Morning: Castillo de San Marcos (The Seashell Fort)

No first‑timer’s visit is complete without the Castillo de San Marcos, the 17th‑century Spanish fort guarding the waterfront. Built from coquina—a natural stone made of compressed seashells—it’s both an engineering curiosity and a striking subject for your camera.

Walk the ramparts, study the rough texture of the walls up close, and look back toward town for classic skyline shots. From the fort, you’re just steps from the bayfront promenade, where boats, bridges, and the fort itself line up beautifully at different times of day.

Photo tip: This is a great spot to shoot the morning sunrise. Because of where St. Augustine is located, you won’t pick up a sunset shot down by the water. But the sunrises are spectacular. Just be sure to arrive at least 45 minutes prior to the rise. The best colors happen before the sun goes up, not afterwards.

Late Afternoon: Lightner Museum & Flagler College

Head back toward the heart of town to step into the Gilded Age. The Lightner Museum, housed in Henry Flagler’s former Alcazar Hotel, showcases decorative arts and curiosities from the late 19th and early 20th centuries.

Just across the way, Flagler College occupies another Flagler masterpiece: the former Ponce de Leon Hotel. The campus is famous for its ornate architecture, hand‑carved woodwork, and Tiffany stained glass in the dining hall. Even a short visit gives you a sense of the over‑the‑top luxury that once defined Florida’s resort boom. This is one of the key stops of your visit.

Evening: Bayfront Stroll & Dinner in the Historic District

As the light softens, return to the bayfront. This is one of the best times to photograph the waterfront, the Bridge of Lions, and the fort from across the water. Then duck back into the historic streets for dinner at one of the many locally owned restaurants and bars—spots like those highlighted by locals (farm‑to‑table kitchens, seafood specialists, and cozy wine bars) give the evening a relaxed, lived‑in feel.

Day 2 – Fountain of Youth, Eco Boat Tour & Lighthouse Climb

Morning: Fountain of Youth Archaeological Park

Lean into one of St. Augustine’s most famous legends at the Fountain of Youth Archaeological Park, said to be the landing site of Juan Ponce de León in 1513. Today it’s a mix of history exhibits, waterfront views, and of course the opportunity to sip from the fabled spring.

The lore says every sip keeps you a day younger; whether you believe it or not, it’s a fun, only‑in‑St‑Augustine experience that connects myth with the real early European presence in Florida.

Late Morning: Eco Boat Tour of the Bayfront

Next, see the city from the water. An eco tour from St. Augustine Eco Tours along the Matanzas River and bayfront offers a fresh perspective on St. Augustine’s skyline, fort, bridges, and surrounding marshes. (Watch the video above to see us on the water!)

Guides often weave natural history—dolphins, birds, coastal ecosystems—together with human history: why the Spanish built here, how the coquina fort worked in practice, and how the shoreline has evolved. It’s a relaxing way to reset between busy walking sessions and a great way to capture wide, contextual shots of the city.

Afternoon: St. Augustine Lighthouse & Maritime History

After lunch, head to Anastasia Island to visit the St. Augustine Lighthouse, considered Florida’s oldest lighthouse and easily one of its most picturesque. The current tower, with its bold black‑and‑white spiral stripes, dates to 1874 and stands 219 steps above the ground.

Climbing is part workout, part history lesson. Landings along the way feature windows looking out toward the sea and back to town, plus exhibits that explain how lighthouses worked and why each tower’s pattern is unique. At the top, you’re rewarded with sweeping views of downtown St. Augustine, the inland waterways, and the Atlantic.

Bonus: Alligator Farm & Nature Encounters

If you’ve still got energy (and curiosity), round out the afternoon at the nearby St. Augustine Alligator farm, where you can safely get close to Florida’s most famous reptiles. Elevated walkways and viewing platforms let you look down into lagoons filled with gators of all sizes.

From downtown, make your way into Lincolnville, a historically Black neighborhood founded by formerly enslaved people after the Civil War. The area offers a quieter, more residential side of St. Augustine, with churches, homes, and small businesses that tell a different story than the tourist core.

If you have time, seek out local museums and markers that interpret Lincolnville’s role in civil rights and the city’s layered history—from Spanish settlement to British rule and later, Loyalist refugees during the American Revolution.

Where to Stay: Historic, Walkable, and Practical

For a balance of cost, quiet, and access, consider staying just outside the tight historic center. In the episode this itinerary is based on, we stayed at the Best Western Historic Inn, about a 30‑minute walk from downtown, courtesy of our sponsor. It offered lower rates and a calmer setting than properties in the city center, plus a full breakfast to fuel long walking days. There is a Best Western right in the center of town, but the rates are higher and you don’t get the breakfast buffet.

So…Is St. Augustine Worth the Hype?

Is it truly the single most photogenic city in America? That’s impossible to call. But after three days of cobblestone streets, seashell forts, legendary springs, and lighthouse views, it’s fair to say St. Augustine is absolutely in the conversation—and a remarkably rich destination for a short trip with a phone in your pocket.

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:

1. Cross the Street: Don’t stand directly in front of the houses. Cross over to the opposite sidewalk to get the full “rainbow” perspective.

2. Go Early: Be there at sunrise. You’ll get soft, even light and—most importantly—no tourists blocking your shot.

3. 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.

4. 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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