St Augustine: From Incarceration to Eternal Youth

St Augustine: From Incarceration to Eternal Youth
By ATD’s Florida Experts, Susan and Simon Veness
Whether you’re in need of a grim incarceration experience or you could really do with taking several years off your tired, creaking bones, the oldest city in the United States has just the thing. Pirates, Spanish explorers, Florida’s multi-millionaires and the undead all called it home, and it’s only a two hour drive from Orlando.

We’re talking, of course, about St Augustine. Located along the Tolomato and Matanzas Rivers along Florida’s Atlantic coast, the city is absolutely steeped in history, the likes of which few places in the U.S. can match. While the year 1565 may not seem old in the U.K., it’s positively ancient history in the States.

Explorer Juan Ponce de León claimed it as Spanish territory in 1513, the French and British got their hands on it, the Greeks dabbled a bit, and native cultures were there long before anyone else. Remarkably, all of those influences are still evident in the city’s historical district to this day. Plus, there were pirates. Which is always cool.


Flight to Freedom St Augustine


Once you’ve reached St Augustine from Orlando it’s easy to get around without a car using the narrated Old Town Trolley’s hop-on hop-off tour (or the similar Red Train Tours), which is the best way to get an overview of the historic district’s shopping, dining, architecture and attractions.  There are 23 stops along the route, and while it would be difficult to fit them all into one day—but easy in 2 or 3 days, allowing for shopping time and the chance to try some of the area’s excellent restaurants, such as The Floridian (start with the Gin Gimlet. You’re welcome) and the superb Café Alcazar, formerly the swimming pool located inside the old Hotel Alcazar, now re-imagined as the wonderful Lightner Museum—we’ll give you the whistle-stop tour of the highlights.


St Augustine


Your Old Town Trolley Tour ticket allows you to ride all day, and includes free admission to the St Augustine History Museum, a free shuttle to the beach, lighthouse, and quirky Alligator Farm, plus exclusive access to the Old Jail, Potter’s Wax Museum and The Old Drug Store. But let’s start at the Trolley’s ticketing compound, and one of the creepiest places hereabouts: the Old Saint John’s County Jail.

In 1891, resident railroad tycoon, Henry Flagler, insisted the country jail be built in Romanesque Revival style so as not to offend the good people of St Augustine’s sensibilities, and on the outside it was beautiful. But on the inside, all manner of “depraved criminals” lived out their sentences under the watchful eye (and brutal cruelty) of the guards, and the villainous warden Sheriff Joe Perry.


Old Saint John's Prison St Augustine


As your group joins one of the “inmates” for a tour inside, you’re waved off with a cheery “Enjoy your incarceration!” Once past the gallows, where prisoners were forced to watch hangings for even minor offences, you enter the women’s jail, where a required minimum of four of St Augustine’s fairest spent their sentence cooking, cleaning and suffering while the men-folk endured hard labour along with their misery. Daily rations included nothing but boiled pinto beans and coffee, and no-one knew when their release date would be…if they survived at all.

Equally, there is nothing made-up about the exhibits in the Pirate Treasure Museum, another stop along the route. This isn’t just the Hollywood version of swashbucklers and their wily ways, though there is an element of movie-making here, too. Instead, much of it is the real deal, with actual artefacts, interactive displays, a recreated pirate ship and a “treasure hunt” the whole family will enjoy.


Pirates Treasure Museum - St Augustine


Further along, hop off the trolley at the St Augustine Distillery, where award-winning craft gin and bourbon are made. Tours are free, as is a rather boozy tasting featuring three cocktail samples, plus samples of the distillery’s gin, rum, vodka, and three kinds of bourbon.


St Augustine Distillery


You might need a nap after that, or, if you’re hearty, move on to the next stop, which is the San Sebastian Winery, again with free tours and tastings. More into all things chocolate? Hold out for Whetstone Chocolate Factory for (say it with us) a free tour and tasting.

Now, we know the idea of visiting a college ranks right up there with dental procedures and non-elective surgery for most people, but trust us when we say the stop at Flagler College is worth doing. First of all, it’s led by student at the college, which means there will be humour and a fair bit of Mickey-taking when it comes to describing what would otherwise be dry, boring history.

Second, visitors get to hear about the founder of this institution, which began its life as a leisure and health resort for some of the wealthiest people in the budding nation, who could afford the $4000 fee per season (January until Easter), which roughly equals $100,000 (£71k ) today. Henry Flagler had some serious issues with wives and with business rivals, so his story is really quite captivating. Not only that, but the building is absolutely exquisite, with literally no expense spared. From the look of all the gold adorning the walls and the ceilings, that luxury is obvious. From the look of the psychotic cherubs carved into the dining room chairs, it’s maybe not as obvious.


St Augustine Distillery


Another must-do stop along the route is Castillo de San Marcos, the protector of the city from 1695 until 1900, and variously occupied, fired upon, and reoccupied by the Spanish, the British, and finally, by newly-proclaimed Americans.

Today, visitors can stroll around the grounds and into the castillo’s various rooms, take a free (with admission) organised tour led by a National Park ranger, chat with costumed ‘soldiers’ and watch cannon firings and weaponry demonstrations.


St Augustine Pirates


The final stop on the tour may just revive your weary spirit, so hang in there for the Fountain of Youth Archeological Park, Florida’s oldest attraction, with its many fascinating experiences beyond the most famous. Our good friend Ponce “discovered” the park’s rejuvenating (if not age-reducing) spring in 1513, or so the story goes. Back in reality-land, history tells a much different story, but the mineral-rich waters of this ‘magical’ spring surely can’t hurt, and it’s even okay to take a drink from the spring and see if it revives you, especially when Florida’s heat and humidity crank up to about a billion. Just don’t expect the sweet taste of victory—or a sweet taste at all (remember all those minerals we mentioned?).


St Augustine


Six Ghost Tours around the city are also available once the sun sets, and with such an old community it’s possible the undead will make themselves felt as you wander the streets by lantern light, or tour from the safety of a ghost train or trolley. Not that brave? See the city on a Segway, by bicycle or scooter, or from the luxury of a horse-drawn carriage ride.

Boating tours, foodie tours, helicopter tours  and biplane rides are also available, but the historic district is delightfully walkable, so put on those broken-in trainers, slather on some sun cream, and enjoy all this rare “ancient” city has to offer!

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