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Florida is a warm haven that attracts many Canadians, along with geese, in the winter. When most of us think about this southern state it is the sandy beaches, leafy everglades and rolling surf that comes to mind. What doesn’t usually surface is the deep history of Spanish, British, French, and Greek influences.

St. Augustine, less than an hour’s drive from Jacksonville on the Atlantic coast, was founded in 1565 and is America’s oldest city. When I travel, I love to dig into a destination’s past and on a recent trip I became acquainted with the forts, ghosts, pirates, robber barons, shipwrecks, myths, legends and original inhabitants of this special place.

When I arrived in St. Augustine, less than an hour’s drive from Jacksonville on the Atlantic coast, I was instantly enchanted with the old part of town, filled with cobbled streets, captivating architecture, romantic inns, cafes, restaurants and galleries. America’s oldest city was founded in 1565 and is filled with ghosts, pirates, robber barons, shipwrecks, myths, and legends. I came solo, but I could see this was a magical place for couples. Everywhere I looked twosomes were taking horse-drawn carriage rides, sitting on the porches of historic B&Bs, and wandering the winding streets, hand in hand. Mental note to self: bring the husband next time!

After checking into the St. George Inn, by the original gates to the Old Town district, the friendly staff quickly helped me get my bearings. From the balcony of my 2nd floor room I could see the coquina walls of Castillo de San Marcos, the oldest masonry fort in the continental United States. Coquina is a tough compound of shell and limestone that protected the town’s Spanish population up to the late 1800s. The location had been home to numerous wooden forts, one notoriously burned to the ground by British Privateer Sir Francis Drake in 1586. Why did this little outpost garner so much attention?  It was a stopover for Spanish galleons piled with Mexican gold heading back to Europe. To protect the plunder from other plunderers, St. Augustine needed better fortifications and Queen Mariana ordered the more permanent Castillo de San Marcos to be built in 1672 (it took 23 years to complete).

My lodging, situated at the foot of pedestrian-friendly St. George Street, was easy walking distance from most historic sites, as well as a multitude of shops and cafes. Each morning, after a generous continental breakfast at the inn, I set out to discover the secrets of this delightfully colorful and compact city.

The best place to start was the Fountain of Youth. Yes, it’s a real place. Kit Keating, a guide at the archeological site, gave me the scoop. Spanish explorer Ponce de Leon landed here in 1513. “We know he stayed for five days and took on water and wood. What he was really looking for was land to claim for Spain and souls for the Catholic church.” Wandering through the site, Kit offered me a cup of water from a spring-fed spigot. It tasted a little sulphur-ish. More of a paint remover than wrinkle eraser. We fed a few of the 50-plus peacocks that make the park their home, then explored a replica Timucua village. “They came up from Venezuela in 2400 BC. When Pedro Menéndez de Avilés arrived to found the Spanish colony the Timucua population was around one million, but they eventually moved on or died of European diseases,” Kit explained.

Pirates and shipwrecks are a big part of the region’s coastal legacy. Treacherous sand banks caused many vessels to be torn apart and in 1824 Florida’s first lighthouse was built in St. Augustine. Due to erosion it fell into the ocean in 1880, but luckily another one had been built further inland a few years earlier. Climbing up the 219 steps of the well-preserved St. Augustine Lighthouse, I got a terrific view of nearby Anastasia State Park. In the basement of the light-keeper’s cottage, I viewed an exhibit called Wrecked! that explained the meticulous care needed to bring up treasures from a ship that went down outside the harbour in 1782. Talk of lost booty naturally led me to contemplate pirates and visit one of the city’s most enlightening and entertaining attractions, The St. Augustine Pirate & Treasure Museum. Interactive exhibits had me shivering as I learned about the exploits of Blackbeard, Captain Kidd and many more. Pirates dealt in terror and were known to torture to death any captain who would relinquish control of his ship. In response, the law went to extreme measures when these criminals of the sea were caught, slicing off their heads or executing them and displaying their bodies in grim cages called gibbets.

More shivering took place that night and I really did wish my husband was with me. St. Augustine has is one of the most haunted places in America with all kinds of ghost tours on offer. I opted for the Haunted Pub Tour, which involved a tipple at each of the four stops. As we began, our guide Lenny Remo handed me a K2 meter. “It measures electromagnetic fields. Watch the lights. If they start to flash it means there might be some ghostly activity.” Our first stop was at the Old City House Inn where Lenny confided a “residual spirit” had been seen. The apparition was thought to be a Spanish soldier who eternally kept watch. A jilted bride who killed her fiancé then herself was also know to make appearances to male guests. Our other stops included O.C. White’s Restaurant, built in 1791, Meehan’s Pub and Scarlett O’Hara’s where we learned of unusual occurrences such as glasses flying across the bar and pictures found hanging upside down. As mesmerizing as the stories were, I was just a little relieved that the K2 meter only flashed once. “Could be an Internet cable connection,” explained Lenny with a shrug.

One of the city’s most commanding figures was Standard Oil tycoon Henry Flagler. His astounding Ponce de Leon hotel, complete with towers, turrets and Tiffany windows was built in 1888 to attract wealthy visitors from the north who would check in with bags of money (literally, since he demanded cash) and stay a minimum of three months. Across the road, he built the Alcazar Hotel with the world’s largest indoor swimming pool with a retracting roof, casino, steam bath, massage parlor and tennis courts. A competitor, Franklin Smith, founder of the YMCA, built the Casa Monica nearby, but Flagler (who owned the railway, the only way to get to St. Augustine) made sure Smith’s supplies never made it and he was forced to declare bankruptcy. These days, Flagler must be turning in his grave since the Casa Monica is now St. Augustine’s premiere hotel. I poked around in the magnificent Moroccan-style lobby, furnished with deep, comfy chairs and made a tasty meal of small plated sardines, roasted peppers, eggplant, cheeses and charcuterie.

The Ponce de Leon Hotel is now Flagler College and students milled about while I took a quick peek at the opulent former lobby. The Alcazar, closed in the 1930s, is now home to the Lightner Museum. The swimming pool has been drained and now houses an excellent restaurant where I lunched on delicious shrimp and strong coffee. After lunch I explored the museum, brimming with the collections of Otto Lightner. A publisher based in Chicago, he encouraged all his readers to be collectors, even of small items such as matchbooks. A primo hoarder himself, one of his most successful magazines was called Hobbies. When the Depression hit, Lightner bought the furnishings and artistic treasures of Chicago millionaires for next to nothing, then put them on display so the public could see how the one per cent lived. As his collections grew he needed a larger space and after staying at the Ponce de Leon he settled on the abandoned Alcazar Hotel which he bought for a pittance in 1946. China, glassware and furniture (including Napoleon’s Grande Escritoire) were on display upstairs and downstairs I gazed at rooms filled with toys, music boxes, hats, purses, jewellery and various Victorian ephemera. Creepy items included a shrunken head from Ecuador, an Egyptian mummy and a stuffed lion named Rota that had belonged to Sir Winston Churchill (presented to him, alive, by the Zoological Society of London in 1943). There was also a lot I didn’t see. “We have more than 5,000 salt and pepper shakers in storage,” my guide Toni Franklin confided.

A place I was a tad squeamish about visiting was the St. Augustine Alligator Farm. Gaping jaws full of razor-sharp teeth are not exactly my thing, but I’m glad I went. Established in 1893 as a curiosity for Flagler’s guests, the farm has since morphed into a zoological park with 24 species of crocodilians from around the world including Africa, Asia and the Americas. The largest was an Australian alligator named Maximo that was 15.5 feet long and 1,250 lbs. I saw him resting at the bottom of a glassed-in pond and he was well deserving of his name.

After all this exploring, I needed some refreshment. At St. Augustine Distillery a passionate guide named Laura explained the distilling process and had our group sample a Florida Mule, made with their signature cane vodka, ginger, lime, simple syrup and a splash of soda. I took a small sip and found it was surprisingly restorative. Attached to the distillery was a bar and restaurant called the Ice House, with industrial beams and concrete walls indicating its original use as an ice plant. The perfect place to bring my husband for a Florida Mule next time I was in the area. Another stop was San Sebastian Winery’s complimentary tasting bar although it was too early for the upstairs rooftop patio’s live music.

Dinner was at Michael’s Tasting Room and what a treat it was. My server brought warmed olives and lightly salted Spanish Marcona almonds. Then I nibbled on small plates of charred octopus, beef tartar, succulent scallops and grilled shrimp, paired with a crisp Sauvignon Blanc. A lovely end to an enlightening day.

In St. Augustine, there is so much more than beaches and boating. This enchanting, romantic city brims with the oldest, most complex and captivating stories in America.

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Maureen LittleJohn
Maureen Littlejohn is Culture Magazin's executive editor. She is a Canadian award-winning journalist who has practiced her craft around the world including in the United States, Africa and Vietnam. Currently based in Toronto, she has a keen eye for detail and has a deep appreciation for the “East Meets West” approach of Culture Magazin. Travel is her passion and she is happy to be able to share her adventures on a regular basis with the magazine's readers.