Correction to This Article
This article gave incorrect drive times to St. Augustine, Fla., from the region's airports. The city is about 40 minutes from Jacksonville International Airport and a little more than two hours from Orlando International Airport.
Desperately Seeking St. Augustine
To Get to the Heart of This Quirky Old City, You Just Have to Know Where to Look

By Stephanie Cavanaugh
Special to The Washington Post
Sunday, November 9, 2008

Each year, when we visit my sisters in Palm Beach County, my husband, Gregory, and I take a side trip in search of our perfect version of Florida, on the off chance that we might someday retire. Someplace close to family, but not too close, if you know what I mean.

Much of what we've seen is as weird as a Carl Hiaasen novel, which has its appeal. But a touch of the gothic (in atmosphere and maybe some Gothic revival architecture) is required, and that's the harder touch to find. Savannah in Florida, I'm thinking, or Key West (so far the closest thing to Our Vision) without the hundred-mile hurricane evacuations.

On paper, America's oldest city seemed perfect. Really old houses, a fantastically loopy history, plenty of palm trees and moss, the ocean just a couple of miles away, and yellow fever hasn't been a problem in the past century.

In fact, it's hard to get a handle on the place. It's as if each of its residents had once had a bright idea for the city's enhancement, had run with it and then lost interest, leaving some unrefined semblance of the original thought. But that's pretty much the history of the city.

St. Augustine has been Spanish, it's been English, it's been Confederate, it's been Union. It's been an asylum for consumptives, a playground for the rich and a get-land-rich-quick magnet for speculators. And all the grand schemes have been undermined by war, fire, water and pestilence. Oh, and pirates: That most famous pirate (um, privateer) of all, Sir Francis Drake, burned the place down in 1586.

Echoes of each influence remain in the architecture and the attractions, making the city enigmatic and, ultimately, fascinating.

Best seen on foot (though there are tour mobiles, trolleys and haunted hearses, should you prefer), the historic district is about the size of Georgetown. Setting out from our room at the St. Francis Inn, we weaved in and out of the narrow cobblestone streets, wandering past Spanish colonial and Victorian homes crowding the sidewalks, peeking at sleepy gardens behind elaborate iron gates.

Lured by the sight of water, we continued along Avenida Mendoza, the main drag along the harbor, to the original city gates and into the Colonial Spanish Quarter, where the cultural dissonance began.

Here, some of the city's oldest buildings, along with some re-creations, are open to visitors, including a living museum of woodworkers and candlemakers and a drugstore with a child-size coffin leaning against a wall. Most of the museum-type places were empty but for us. The bigger visitor draws were the T-shirt and tchotchke shops in every other building. Williamsburg meets the Ocean City boardwalk.

The scene made us . . . itchy, so we headed for the county beach on Anastasia Island, a quick drive away.

Beware confusing the beaches. While the state park has four miles of pristine sand, herons and nesting sea turtles, St. Augustine's hard-packed county beach is just the place for families that can't be parted from their SUVs. You're welcome to drive right up to the waves with your Pringles and surfboards. Watch out for sand castles if you need to back up when the tide comes in.

The next morning I'm scribbling notes at a table beside the dinky pool at the St. Francis, glaring at the rumbling air conditioner and other industrial apparatus alongside the building. This is so not the lush tropical setting artfully pictured on the Web site.

We prefer bed-and-breakfasts to hotels because we love old homes and frequently find kindred spirits in the hosts and guests. This inn's particular allure was its 1791 vintage and reputation as the most haunted house in St. Augustine -- buttressed by excellent reviews on, usually so reliable a travel resource, and the aforementioned Web site.

A ghost or two would have livened things up. Snapshot: Our fellow guests gathered in the parlor that evening to listen to an elderly gent doing his impression of a tipsy Dean Martin singing "Strangers in the Night."

St. Augustine is depressing me, I grumbled in my journal. But shortly thereafter, perhaps because of the coffee or maybe the act of checking out, I was enchanted.

In the early morning cool we strolled into Lincolnville, once the heart of black St. Augustine, a 45-block neighborhood of Victorian mansions jostling modest bungalows, where it seems every other house has a sign saying Martin Luther King Jr. slept or spoke here, because he did. St. Augustine played a pivotal role in the passage of the 1964 Civil Rights Act.

Downtown again, we browsed a few art galleries, drank more coffee and admired the Spanish-style buildings with their fantastic spires and turrets and orange-tiled roofs. Though laid out by the Spanish and remaining true to the original plan, much of the central city was fashioned in the late 19th century, when Henry Flagler made this a playground for rich Northerners (before moving them south in search of balmier winters).

Flagler's Ponce de Leon Hotel is now Flagler College. His Hotel Alcazar now houses City Hall and the Lightner Museum, where an antiques-filled hall has replaced the vast indoor swimming pool. The Casa Monica Hotel, not built by Flagler though he owned it for a time, was magnificently restored in 1999. A vintage Model A Ford is stationed in the porte-cochere.

Across the street from the Casa Monica, the Government House, the city's administrative center (in one form or another) since the 16th century, is now a museum. Essential purchase here: "The Houses of St. Augustine" by David Nolan, a beautifully written and illustrated architectural history of the city, and the perfect walking companion.

I confess that shopping, or more accurately browsing, quirky one-of-a-kind spots is always high on my lowbrow list of things to do to get a feel for a city. So the shocker was finding that, instead, the last place on our tour, the historic Castillo de San Marcos, was the place I should have gone first to get my bearings.

Completed in 1695, the oldest fort in the United States was big enough to hold the entire town -- and the town's animals -- when under siege, which it was, frequently enough.

Inside the fort, park ranger Jeffrey Edel, muffled in full Spanish military regalia (wool, no less, on this 95-degree day), called out jovially, "Come into the shade. Lecture in two minutes." And the other tourists scattered like rats, fleeing for the exhibits within the thick walls of the fortress. That left me to plop on a bench and have Edel to myself until Greg finally abandoned the cannons displayed up on the gun deck.

The early history of the city is stunning. Who knew that Spain sent 800 settlers to this area, only 26 of them women, expecting them to intermarry, in this case with the Timucuan Indians? It was the pattern, Edel explained. "That was how a small country like Spain was able to colonize a good bit of this continent."

Who knew that the Spanish, with no history of slavery, attracted slaves from the British colonies to the north of Florida with the promise of land -- and freedom -- in exchange for converting to Catholicism? Oh, and intermarried with them as well. No, it's not taught in our history books, Edel said. "The original underground railroad ran south."

We knew (didn't we?) that the town and the people would stink, given the unwashed bodies, rotten teeth and a diet rich in garlic. But we didn't know that wool can be cool in the tropics, sodden with sweat and cooled by the breeze.

Edel hasn't cleaned his uniform in the five years he has been wearing it. The wool airs out overnight, and he "Febrezes it now and then," he said.

It is not until the end of Day 2 that sense was made of the city, and it was Edel who finally made harmony out of the city's dissonance. "There are three or four different St. Augustines," he said. And each is best viewed separately.

"There's historic St. Augustine with the Castillo and the Lightner," he said. "The artistic St. Augustine: There are art galleries all over town. There's the beach town. And if you're looking for beautiful Victorian architecture, this is the place to study it. Flagler College has Tiffany stained-glass windows in the lunchroom. Memorial Church is a replica of St. Mark's in Venice . . . ." He paused. "This is old Florida, and the most European city this side of Quebec.

"You just have to sort through the tourist stuff," he finished with a laugh. "That's the St. Augustine we don't talk about."

Stephanie Cavanaugh last wrote for Travel about the Inn at Montchanin Village in Delaware.

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