ST. AUGUSTINE, Fla. â In a twist on traditional romance, my partner and I celebrated our first anniversary by exploring the eerie charm of America’s oldest city. St. Augustine, founded in 1565, offered a unique blend of history, mystery, and unexpected romance.
When my partner and I were planning what to do for our first-year anniversary, we knew we wanted it to be romantic. That, of course, was a given. We also knew we wanted it to be something the two of us would really enjoy and look back on fondly. Thankfully, we are both into history, which was easy to find, as there are plenty of historical sites around. Finally, we wanted it to be somewhere we had never been to before, yet still close enough to us that we could drive away just for the weekend and be back in town by Monday.
Now that really narrowed down some of our options. Luckily, we were okay enough with St. Augustine being the choice, as it happened to encompass all of those. What we didn’t know before was just how âhauntedâ the place supposedly was.Â
Our journey began at Flagler College. Along with our self-guided tour of the vintage Floridian architecture, we stepped through Ponce de Leon Hall and to the West Lawn, accompanied by koi fish and the Palm Garden, which was short and sweet enough until we encountered our first ghostly tale â the Woman in Black, Henry Flagler’s haunting mistress. Undeterred, we ventured onto St. George Street, the town’s oldest thoroughfare, sampling wines and delving into pirate lore at the Pirate and Treasure Museum.
The Castillo de San Marcos, a 450-year-old Spanish fort, stood as a testament to the city’s tumultuous past. Despite the sweltering April heat, the experience was captivating. It was truly a dream to see a real-life castle right along the Florida coast.Â
We had dinner at a restaurant on the beach. We timed our reservation perfectly with the sunset, and after a celebratory champagne and a delicious slice of cheesecake, we walked out, hand in hand, onto the St. Augustine pier.Â
There, we stood, in the bleeding orange sun, and exchanged promise rings. It wasnât much, the rings werenât some thousand-dollar trove like the treasure we had seen in the museum, it wasnât any diamond that had formed in the ground before the Castillo had even been thought up, but it was something both she and I knew we would never forget.Â
Then, right there on the top of the pier, it started to rain. It wasnât just a little sprinkle, nope, Mother Nature must hate sapphics or something because it started to pour. Fat, cold drops plopped right down onto our satin and lace, and we knew if we continued with the ghost tour that we were supposed to take that evening, it would be absolutely miserable, so we did the next best thing: hit the bar.Â
The bar we ended up at was just outside of the old St. George Street. It was an old-timey-ecclectic sort of spot with a hidden speakeasy behind a bookshelf. We only got two drinks each, but we were there for hours, just chatting between ourselves and the bartender about how our trip had gone so far. She talked about the koi fish and the little artist markets along the main road, and I raved about the pirate museum and the view of the water from the top of the Castillo. There, we toasted to our adventure, recounting the day’s discoveries.
The following day took a darker turn as we explored the Old Jail, built in 1891 as Alcatraz’s prototype. The tour culminated at the gallows, a chilling reminder of the site’s grim history. That left us with a super unhopeful thing to think about, as we passed the Fountain of Youth on our way back to the car.Â
Our next stop, the St. Augustine Lighthouse, is reputed to be the world’s most haunted. We took our time, learning the history of the lighthouse and walking up the stairs, all 219 of them, until we found ourselves at the windy top, overlooking the gorgeous panoramic coastal landscape â and sharing a moment of playful terror as I pretended to fall, much to my height-fearing partner’s dismay.
The evening brought a Prohibition-era-themed dinner and a rescheduled ghost tour. We learned that St. George Street was built atop old hospital grounds and battlefields, adding a macabre layer to our earlier explorations.
Our final stop was the legendary Love Tree. The Love Tree is a real tree, planted by two lovers. One favored a palm tree, and the other, an oak, but as the two trees grew, they grew into one another, becoming entangled and intertwined within the stems of each other. The legend now goes that whoever kisses under the tree shall have a love that lasts eternally. So, in the spirit of our anniversary, thatâs exactly what we did, where we sealed our visit with a kiss, embracing the local lore of eternal love.
This unconventional anniversary allowed us to see that romance can flourish in the most unexpected places. In St. Augustine, we found that love, like the intertwined Love Tree, can grow stronger amidst the shadows of history.