America's Longest Stretch of History in St. Augustine, Florida
Story and photos by Tim Leffel



After centuries of pirate raids, native skirmishes, a mighty fort, and an ambitious railway stretching to the south, the USA's oldest city now just makes you battle over-indulgence.


St. Augustine fort

I take a few gulps from the Fountain of Youth, which tastes a whole lot like what comes out of my apartment tap a few hours away. I don't feel any younger. Maybe though, I negated the effects with the excellent barbecue from Smoked I wolfed down just outside the gate. Add a few days of life here, subtract a few there, and it's a wash.

I'm not expecting much from the Fountain of Youth Archaeological Park, figuring it will be as Florida cheesy as Weeki Wachee or the Skunk Ape Research Headquarters. It turns out to be a well-designed, attractive place though, with a long walkway out through the wetlands to the inlet, where we can spot herons in the shallows. People in period costume give demonstrations on blacksmithing, cannon firing, and muskets.

Fountain of Youth Park Archaeological

The Battles for Saint Augustine and La Florida

When Ponce de Leon landed on the coast of this new land in 1513, he named it La Florida and went searching for gold and a legendary fountain of youth. He didn't find either, but he did inadvertently discover the Gulf Stream. He noticed that his ships were moving very quickly up the coast of this region and eventually this fast track to home became the main reason the Spanish wanted to claim and protect this coast.

He died of a shot from a poison arrow though and wasn't the real founder of Saint Augustine. Neither was De Soto, who died after wandering around the swamps for three years and finding nothing of worth. A few explorers followed and decided that the combination of snakes, alligators, insects, humidity, and hard-fighting natives made the area too risky for settlers. It wasn't until some French protestants started settling in Florida that the Spanish king changed his mind and in 1565 he sent Don Pedro Menendez de Aviles to show the Huguenots who was boss.

Castillo de San Marcos fort Saint Augustine

Menendez and his nephew that took over later didn't have an easy time here. For decades they dealt with erratic food supplies, mutinies, Native American attacks, French attacks, the British navy, and struggles against the elements. Invaders ransacked and burned the town multiple times, so none of the buildings in town are truly original. Pirates were such a threat that they influenced city planning: Treasury Street is just seven feet wide. This street leading to what used to be the Royal Spanish Treasury was meant to be wide enough for two men to carry a chest of gold to the port, but not wide enough for a horse-drawn carriage to quickly rob the place and make off with the loot.

The Castillo de San Marcos fort changed everything. The oldest masonry fort in the USA took 23 years to finish and has stood strong since 1695. The British, who were setting up their own ports and settlements further north, attacked it just seven years later. They burned the town nearby—again—but couldn't get past the fortress walls. They tried again in 1728 and again in 1740, but were never successful. This part of the new world didn't come under British rule until the Treaty of Paris in 1763, right before the colonists started revolting. It soon became a prison, at one point holding three men who signed the United States Declaration of Independence.

It went back to Spain for decades, then became part of the U.S. territory of Florida in 1821. The independent Americans weren't any more enlightened though, mostly using it as a prison for holding Seminoles and other tribes while they annexed their lands. It became a National Park Monument in 1924 and is now part of the U.S. National Parks Service.

We go inside to see the old barracks, the weapons storerooms, prison areas, and displays that detail the history of the fortress. A cannon firing demonstration up top gives a feel for the days of battle when an enemy ship came sailing into the inlet.

From Rum Runners to Rum Makers

St. Augustine Distillery tasting room

Now St. Augustine is a place of pleasures, though not the kind the early settlers and soldiers experienced in the brothels along the main drag. Now those buildings are filled with boutique hotels, nice restaurants, and bars serving Florida craft beers on tap. It's a family-friendly place now, with as many ice cream shops as taverns.

One of the most popular stops is a chocolate factory, at the Whetstone Chocolates company established in 1967. We join a tour and learn about the health benefits of cocoa and what separates the quality artisan chocolate from a place like this from the mass-market bars sold by the international conglomerates. We go up the scale with cocoa content as we tour the facilities, from white chocolate (0%) through 31% milk chocolate, "De Leon" 47%, "De Soto" 64%, and "Menendez" 72%.

I am more excited about the St. Augustine Distillery, located in an old ice house and showing an admirable flair for preservation and design. It's a progressive company too: they use corn-based resin cups in the tasting room that break down and biodegrade, plus all the spent grains go to farmers for fertilizer and they use a zero-wastewater discharge system for fermentation and cooling.




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