St. Augustine Historic District Ideal for Family Trips, Girls’ Getaways and Romance

Whether Looking for History, Adventure or Love, Your Perfect Trip Awaits

St. Augustine is nothing if not enduring.

The city's brick-lined streets, horse carriages, forts and grand hotels have charmed me at every stage of my life. My first visit at 14 was on a family vacation. I returned seven years later for a weekend with my best friend. Recently, on a romantic week with my husband, I discovered yet another side of the oldest city in the America.

A New "Old World"

I first set flip-flop on St. George Street the summer before starting high school. My brother Matthew, then 12, and I were set loose for a few hours. We passed through the coquina stone pillars that marked the historic city gates. The ancient street was closed to vehicles, leaving us to run back and forth between the shops.

We stumbled upon The Oldest Wooden School House, interrupting our summer dedicated to anything but learning. The cedar and cypress planks of the more-than-200-year-old building were washed by weathering, but the structure's history lit up even us, the pupils at recess. We learned how the schoolmaster and his wife lived above the classroom and we even got to see some of the textbooks kids our age would have used centuries ago.

Next we found the Colonial Quarter, where blacksmiths and woodworkers roamed about the 18th-century courtyard, giving demonstrations and entertaining groups.

Adventurous Spirit

One Friday afternoon years later, my friend Ommy and I left Gainesville for St. Augustine without even a toothbrush. We planned to visit for the afternoon, but stayed the weekend.

That night we had dinner in the torch-lit courtyard of Harry's Seafood. Not feeling like leaving The Old City, we checked into the Pirate Haus Inn, a hostel right in the middle of the historic district.

The Castillo de San Marcos was our first stop. Built by the Spanish from 1672 to 1695, it is the oldest masonry fort in the U.S. That afternoon we toured Flagler College, the former 1887 Hotel Ponce de Leon, which is now on the National Register of Historic Places.

We capped the night off with Old Town Trolleys Ghosts and Gravestones' "Frightseeing" Tour of nighttime St. Augustine. Aboard the trolley of the doomed, the "ghosts" we encountered on the tour, especially at the Old Jail, were so convincing, I became a believer in this city's ancient mystique.

A Quixotic Sanctuary

For our one-year anniversary, my husband, Chet, and I enjoyed a weekend retreat at the Kenwood Inn B&B. The 1880s house is in the historic district just one block from the Intracoastal Waterway, which we could see from our third-floor honeymoon suite.

One evening we took a sunset cruise on the Schooner Freedom, a 72-foot sailboat. The cruise left from the marina across from the Inn and was complete with hors d'oeuvres and wine. The skies were cloudy that night, but the relaxing ride was just right.

The next night we feasted in the velvet-draped Costa Brava – an elegant restaurant located in the beautiful Casa Monica Resort & Spa. Built in 1888, the Casa Monica was restored to its former glory and re-opened in 1999. Leaving the restaurant, we were greeted by the impressively-lit Lightner Museum. It is another of Henry Flagler's former grand hotels (this one, the Alcazar) and today it holds a wonderful "collection of collections" featuring one of the world's largest displays of cut glass – as well as Victorian art and furniture.

The evening ended with a stroll up and down the dimly lit streets of the historic district. We rounded a corner and found a small courtyard lit with white lights and couples dining quietly on Italian food at La Pentola. I smiled to myself and took it as a sign that new treasures will always be found on my trips to St. Augustine.