If the thought of a Florida vacation conjures images of drunken spring breakers and white-haired snowbirds shuffling around golf courses brandishing nine-irons, it might be time to broaden your view. The penultimate stop on our recent Florida road trip found us smack in the middle of the oldest city in the United States: St. Augustine.

We left downtown Orlando and headed northeast to the coastal city of St. Augustine. The farthest north in Florida we’d ever been, we knew that despite the fact it was late February, the weather might not be beach-worthy. We were right. But we weren’t quite prepared for were the extraordinary historic landmarks that make up this little gem of a town.

Founded by the Spanish conquistadors in 1565, St. Augustine is sometimes described as the longest-established city in North America. However, St. John’s, Newfoundland here in Canada was established in 1497 and Mexico City in 1325. But it is the oldest “continuously-inhabited European-established settlement” in the US (at least according to Wikipedia). And that Spanish influence is evident throughout the little streets of the old town.

The town has a lengthy and storied history: invasions by pirates in the sixteenth and seventeenth centuries, a British loyalist haven after Florida was ceded to Great Britain in 1763, changing hands several times to one of the most interesting parts of its history: the “invasion” of tourists brought by the extension of the railroad in the late 1800s.

Henry Flagler, one of the owners of the Standard Oil Company (with J.D. Rockefeller) enjoyed winter in St. Augustine in 1883 after which he decided to form a new railway company to lure wealthy Americans from wintery places like New York and Boston south for the winter season. He built two hotels: The Hotel Ponce de Leon and the Alcazar. He then bought the already-established Cordova Hotel and the town flourished. That is until the railroad was extended farther south to Miami where visitors could count on warmer weather throughout the entire season. St. Augustine was no longer the winter darling of the northern visitors.

Even today, though, those old hotels are triumphs of Spanish colonial architecture and are still wonderful to see experience.

The Hotel Ponce de Leon is now the beautiful home of Flagler College as the two photos below show…

…and the Hotel Alcazar is a museum, both worth visiting. We did. Here are two shots that evoke what it must have been like “back in the day.”

And then there’s the old Cordova Hotel that Flagler renamed The Casa Monica. Well, that hotel is now part of the Marriott Autograph collection of quirky hotels and it’s where we stayed. We spent two nights in the two-story St. Francis suite, a nice upgrade for two very loyal Marriott guests!

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The view from our suite…

…and the Casa Monica lobby…

We had already experienced a lot of “quirky” places on this road trip (Orlando, Sarasota) but this one was different. Although those little streets in the old town suggest it storied past, they largely house tourist “traps” that you might enjoy.

We enjoyed walking around and seeing what was there but we’re not really the tourist-shop kind of visitors. Instead, we walked miles over to the island and explored as many of the quiet streets as we could.

When it was time to pull out of St. Augustine, we were headed to our last stop: Fort Lauderdale, that hotbed of drunken spring breakers. No kidding!