Vail Daily travel feature: Exploring Florida’s oldest city |

Vail Daily travel feature: Exploring Florida’s oldest city

Katie Coakley
Daily Correspondent
El Galeon, a replica a ship that traveled the coasts of Florida between the 16th and 18th century, currently docked in St. Augustine.
Katie Coakley | Special to the Daily |

as we walked down the cobblestone street, I was momentarily taken aback as a Spanish conquistador passed on my left, jostling my arm.

“Excuse me,” he said, in perfect American English.

“No problem,” I replied, stealing a glace at his doublet and buckled shoes.

It wasn’t a singular occurrence, this running into history on the streets of St. Augustine. During the weekend, I also encountered a colonial woman, a turn-of-the-century sheriff and one disheveled pirate with a more-than-passing resemblance to Captain Jack Sparrow.

Not to mention the ghosts.

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But that’s the charm of Florida’s oldest city; it’s a melding of old and new. St. Augustine will celebrate its 450th birthday next year, but the time to visit is now.

Stroll through the centuries

One of the most striking features of St. Augustine is its architecture. From the coquina walls of the Castillo de San Marcos to the Spanish Renaissance style of what is now Flagler College, it’s possible to cross centuries during just a short stroll through the city’s Old Town.

St. Augustine’s history is flavored with a wide variety of influences. When Spanish explorer Pedro Menendez de Aviles settled the area in 1565, the Timucuan Indians were already living there; you can learn more about these indigenous people at the Fountain of Youth Archaeology Park, which is located on what was once the Timucua village of Selloy.

The Spanish settlement can still be felt today in St. Augustine. Visit the Castillo de San Marco, which rises above the seawall in the Old Town, and see the oldest masonry fort in the United States. Stay for a cannon demonstration and be sure to inspect the coquina from which it was constructed. The Colonial Quarter, a living-history museum in the center of Old Town, has recently been updated and expanded. You can explore three centuries of St. Augustine’s history with the help of authentically costumed historic interpreters, ranging from the founding of the city through the British occupation.

Much of the Spanish Renaissance style of architecture, the iconic buildings that have won St. Augustine the title of one of the prettiest towns in America, are a contribution of Henry Flagler. Flagler, who is best known as the founder of the Florida East Coast Railway, built the impressive Hotel Ponce de Leon in 1888 as well as the Hotel Alcazar; these buildings are now Flagler College and the Lightner Museum, respectively. The Villa Zorayda, a one tenth scale of a section of the Alhambra Palace in Granada, was once a winter residence but is now a museum as well.

Then there are the “oldest” attractions. One of the benefits of being the oldest city in the United States is that it’s also home to many of the oldest attractions as well. Stop by the Oldest House and tour the museum before visiting the Oldest Wooden School House in the USA. As with any museum experience, a visit to the Oldest Store might be in order, too. Feeling overwhelmed? Hopping on one of the many tours, like the Old Town Trolley Tour, is one way to learn more about the many highlights. It’s a 70-minute tour that includes more than 20 scheduled stops.

Perhaps one of the most interesting aspects of St. Augustine is the role the city has played in civil liberties in America. From the beginning, when Pedro Menendez landed in 1565, to the establishment of Fort Mose, the first freed black settlement in the U.S., and through to the Civil Rights Movement in the 1960s, St. Augustine has seen — and influenced — the course of history. To learn more, visit Journey: 450 Years of the African American Experience, an exhibit that elevates awareness of the role that African Americans played in the cultural and historical development of St. Augustine. The St. Augustine Civil Rights Museum and St. Augustine Black Heritage Tours provide other opportunities to learn more.

Eat, drink and be merry

With so many locales to explore, it’s necessary to fortify yourself accordingly. St. Augustine has embraced the farm-to-table ideal, with many restaurants focusing on locally grown produce and, of course, taking advantage of the great variety of seafood.

St. Augustine has some unique snacking options that are definitely worth a visit. Hyppo Gourmet Ice Pops creates unique flavor combinations utilizing fresh, all-natural ingredients. The strawberry datil pop (datil is a type of pepper that’s only found near St. Augustine) was a refreshing blend of sweet strawberry with a pleasant spicy burn at the end. Looking for something more substantial? Cousteau’s Waffle and Milkshake Bar is home to the wonut: a hybrid waffle and donut concoction. Wear a red beanie and you’ll receive a discount.

For liquid libations, the San Sebastian Winery produces several different varietals from hybrid and native Muscadine grapes. Tours are offered daily along with opportunities to sample the goods. The Cellar Upstairs, a rooftop bar, is a great spot to listen to live music. St. Augustine is a hub for wine lovers; it’s impossible to walk around Old Town without seeing at least five different opportunities for a wine tasting. Be sure to sample responsibly.

One of the most exciting additions to the libations scene in St. Augustine is the opening of the St. Augustine Distillery at the historic Ice Plant. The Distillery is producing small batch, premium spirits using locally grown ingredients, like heritage sugar cane. The story is lovingly detailed on the tour and the tasting (the Distillery is currently only sampling vodka as the whiskey is aging at the moment) reinforces the fact that the Distillery is a welcome — and tasty — member of the community.

If sampling and tasting has whetted your appetite, head to one of St. Augustine’s many fine dining establishments for sustenance. The Floridian, whose interior is a cozy blend of kitsch and comfort, specializes in local and sustainable ingredients; the menu is a blend of southern comfort with many vegetarian and lighter options blended in as well. Catch 27 is known for its fresh caught seafood and, though a bit further afield, Cap’s on the Water is the perfect location with a view for lunch or brunch.

It’s impossible to detail everything that’s happening in St. Augustine and a weekend is barely enough time to scratch the surface. However, the town has survived and flourished for 450 years — it’ll be waiting for your visit.

Katie Coakley is a freelance writer and part-time Colorado resident who likes to travel, drink beer, sip whiskey and then writes about it. You can follow her adventures on her blog, or by buying her a pint on a sunny deck

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