Saint Augustine, FL

Let's Spend a Day in America's Oldest City

Rene Cizio

There’s music playing from seaside cafes and long-haired retirees driving by on trikes and bikes. There are oodles of people wearing swimsuits with subtle coverups, and the scent of suntan oil wafts on the breeze. Local shops sell brightly colored swimwear and kitschy souvenirs that say things like “Life is better at the beach” while children are chased by their parents as they cross the brick-lined streets. It’s loud, busy, colorful, and entirely St. Augustine, Florida.

There’s also a lot of history – it’s the oldest city in the United States.
Photo byRene Cizio

As I was driving to St. Augustine, Florida, I spotted a big black bear seated in the back of a pickup truck. It encompassed most of the bed. When I took a double take, I realized it was stuffed. The truck had a Florida license plate. I laughed and wondered, is Florida as weird as everyone says?

I’ve been to Florida several times, but always for short stints of a week or less and always in different places. I’ve been to Miami a few times and through the entirety of the keys and Fort Lauderdale. Now, remembering those trips, maybe Florida is a bit different. Is there any other place that can claim neon as its state color? I kid, but just a bit.


Today, most people know the city for its Spanish colonial architecture and Atlantic Ocean beaches. Still, in the past, it was known as a fortress surrounded by a protective barrier wall complete with guarded city gates.
Photo byRene Cizio

Spanish admiral Pedro Menéndez de Avilés founded St. Augustine in 1565, making It the second oldest continuously inhabited European city in the United States (San Juan, Puerto Rico, is the oldest). To give context, consider that the American Revolution began in 1775.

The city was under Spanish rule until they ceded Florida to the United States in 1819. Though St. Augustine is the oldest city in the country, you might not know it by looking. Maybe the fountain of youth keeps the place from showing its age, but it is there in the details. Let’s take a look.


When you enter St. Augustine, you’ll find brick-lined streets and Spanish flavor, with centuries-old buildings, horse-drawn carriages, and hidden courtyards.

In the early days, there was a lot of piracy and battles against local American Indian tribes, the English settlers in Jamestown, the British, and others. The “ownership” of the land changed many times until the American colonialist won, displaced the native, Spanish, and British populations and turned it into what it is today: a tourist destination with a great history.


The Castillo de San Marcos is the oldest masonry fort in the continental United States. The Spanish built the Castillo to defend Florida and the Atlantic trade route. Inside is a museum where you’ll find historical artifacts, pottery, currency, furnishings, documents, maps, and architectural drawings.
Photo byRene Cizio

Approaching the Castillo, you’ll see the original parameter wall along the coastline. You’ll also see the line to get in because it’s long.  Tickets cost $15 per adult, good for seven days, but entry is free with a national park pass.

Fun fact: The floors of the Castillo are tabby – tabby is a mixture of burnt oyster shells to create lime, mixed with water, sand, ash and broken oyster shells that form a type of cement – a modern mixture protecting the historic floors below.


The Fort Matanzas National Monument specifically preserves the 1742 coquina watchtower adjacent to the Castillo. It was critical to defend the southern approach to St. Augustine and about 300 acres of coastal barrier islands, salt marsh, dunes, forest, and other plant life along the Matanzas River on Florida’s Atlantic coast.
Photo byRene Cizio

Fun fact: Coquina, unlike tabby, is a natural rock made of compressed fragments of various shells and mollusks.


“Who goes there?” That’s something a guard might have asked if you tried to enter St. Augustine in 1808 when stone masons built the coquina city gates. Back then, it was a forfeited city with a wall and the Castillo to protect it. People could only enter by the guarded city gates and a wooden drawbridge over a moat. Yep. You can see gates like these across Europe, but do you know where else in the United States you’ll see them? Nowhere.
Photo byRene Cizio

The St. Augustine city gates have stood at the north end of St. George Street for over 200 years.


In case it wasn’t clear what would happen if you tried to enter the city without permission, the old Huguenot Cemetery is right across the streets from the gates and the Castillo. Huguenots are a French Protestant sect, and, according to the sign out front, this cemetery was a Protestant burial ground between 1821 and 1884.
Photo byRene Cizio


After you enter the Old City Gate, you’ll be on St. George Street. It’s a pedestrian-only street that leads to the Plaza de la Constitucion.

St. George Street is a historic pedestrian road with galleries, restaurants, bakeries, cafes, candy shops, ice cream parlors, and attractions. You’ll find fudge, pirate punch, saltwater taffy and plenty of pirate-themed t-shirts and sea shells.
Photo byRene Cizio

The street has a few historic buildings, but most of it has been recreated to look like a historic city. Vendors and tour guides parade around in historic-looking clothing, many dressed as pirates and trying to pull tourists into their shops and attractions.

The wooden schoolhouse is near the gates. You’ll spot it easily because it’s 200 years old and made of red cedar and cypress planks. The signage will help you find it among other recreated buildings. Likewise, the whitewashed Pena Peck House has a sign saying it was occupied by Spanish Royal Treasurer Juan Estevan de Pena.
Photo byRene Cizio

There is a gruesome-sounding Medieval Torture Museum that displays torture devices with mannequins representing people. Toward the end of the street, the Colonial Quarter is an outdoor space with various entertainments and tours to learn about blacksmithing, live musket demonstrations, and other pastimes as an early European settler.

I walked around the cobblestones like a Spaniard might have, weaving around tourists and avoiding the old women in bikinis carrying political flags like I was inside a video game.


There were a few historic houses, and like many southern homes, some were pretty spectacular, but there’s also The Lincolnville Historic District. St. Augustine’s historically black neighborhood is associated with many significant events in the city’s African American history. It includes the highest concentration of Victorian-era buildings in St. Augustine.
Photo byRene Cizio
  • St. Mary’s Missionary Baptist Church on Washington Street
  • St. Paul’s AME Church on M.L. King Avenue
  • D.M. Pappy’s House on Oneida street
  • Yallaha Plantation House on Bridge Street. It’s one of the oldest residences in Florida, dating from 1800
Photo byRene Cizio


The Fountain of Youth has been fabled as a mysterious source of sacred, therapeutic waters, but sadly, I found it’s mostly clever marketing. It’s a privately owned 15-acre commercial enterprise and has always been – at least ever since white people arrived.

Now they’re marketing the site as an “archaeological park,” which is more accurate but still a commercial business. I point this out because I thought it was a state or even national park-run site, but it isn’t.
Photo byRene Cizio

However, there has been some important history connected with the land, if not the water. Archeologists have excavated the remains of 90 Native Americans – interred in Christian burial. The math isn’t hard – the site was the first Catholic mission in the U.S. The missions later expanded across the country with Cross and Crown Spanish colonialism. The kings sent Franciscan friars, established churches and large plots of land and recruited American Indians to live there. The missionaries’ pitch was that they would provide stable food, shelter and safety in exchange for conversion to Catholicism, work at the mission, and adherence to the rules. If you didn’t want to convert, a grave would be arranged for you instead!

It has been touted as the 1513 Florida landing site of Ponce de Leon, but the details are murky. What’s clearer is that savvy marketers have managed the land for a long time. It cost $18 to go inside, so I didn’t. But let me know if you do or have.

Pro tip: Watch out for the free-roaming peacocks! They’re pretty but hate tourists.


If you’re looking for a place with a variety of things to do, lovely beaches, modern amenities and great history, St. Augustine is an excellent vacation spot. They offer carriage, trolley, bus, and walking tours, among others. There are plenty of people to teach you about history and others to indulge your whimsy on the beach. It’s up to you, but if you like a Florida vibe, there’s something for everyone.

Read more stories about Florida on my blog.

Comments / 0

Published by

Solo traveler stories about places and things to do

Detroit, MI

More from Rene Cizio

Comments / 0