St. Augustine: Oldest city in the nation is worth a visit


By Sarah Sekula, published on

ST. AUGUSTINE — It’s a bluebird day in July as I spot the Castillo de San Marcos in the distance. Made of crushed coquina shells and rows of cannons, it stands firm on the edge of the Matanzas Bay. A relic of the 17th century.

But instead of mingling with the masses, I’m cozy aboard a 27-foot Stiletto catamaran with some newfound friends: a family visiting from Tennessee, a local couple kicking off a birthday celebration and a captain who is equal parts entertaining and genius.

As we approach Vilano Beach, the skim boarders zipping across the water capture our attention first. Seconds later, an Atlantic bottlenose dolphin breaks the surface, and our chatter turns to oohs and aahs. Better yet, Captain Zach McKenna, interpretive naturalist and owner of St. Augustine Eco Tours,  recognizes the creature.

A dolphin’s dorsal fin is like a human fingerprint with different identifying notches, he explains. This happens to be a dolphin that he sees on a regular basis.

The unique shape and notch pattern on the dolphin’s dorsal fin help us identify the animal, he explains. This happens to be a dolphin that he sees on a regular basis.

“That’s a tail dive,” he says, as the graceful creature disappears. “It indicates the dolphin is going a bit deeper.”

Pretty impressive. And I’m not just talking about the marine life. McKenna knows his stuff. After spending more than two decades exploring the Florida coast, he has amassed an arsenal of experience and information.

Beverly Sanford, who has been on 20 excursions with McKenna’s company, can attest to that.

“My husband refers to him as a ‘scholar’ of the water,” she says. In turn, the exploratory trips over the past nine years have given her family a deep appreciation for marine life.

“We keep coming back for rest, family time, inspiration and solitude,” she says.

It’s easy to see that McKenna enjoys nothing more than showing people the less explored areas of St. Augustine. And there are plenty. Overall, there’s an impressive 73,000 acres of protected ocean, beaches, coastal scrub, salt marsh, mangrove estuary, freshwater marsh, maritime hammock and pine flatwoods to peruse.

Sure, St. Augustine doesn’t get the attention that its neighbor Orlando does. And that’s exactly its appeal. It’s unassuming and authentic, and it has a big birthday coming up: the city turns 450 on September 8.

Step back in time
For a peek at the Ancient City’s history, I stop by Flagler College, built as a hotel by self-made millionaire Henry Flagler in 1888. In its heyday, it was an exclusive resort where five former U.S. presidents stayed. In fact, it had electricity three years before the White House did. With stunning Spanish Renaissance architecture and original artwork, it’s no surprise that it’s a National Historic Landmark.

My group gathers outside in the courtyard, staring at the words etched in Latin at the entrance.

“Doesn’t it say something like no tortillas and more eggs please?” asks the lady next to me.

“Actually, it’s something along those lines,” says the tour guide. “Henry Flagler had a sense of humor.”

With a collective chuckle, we enter the building. The wonder continues. In the grand lobby we are wowed by the 68-foot domed ceiling supported by eight females figures serving as columns. Next, we waltz into the Hogwarts-style dining room. Hand-painted murals hang on the walls. Sunlight pours in from 79 Tiffany stained-glass windows. Here, it’s easy to envision a certain bespectacled boy wizard chatting up Hermione or receiving an owl post.

The tour ends in the Flagler Room. Ceilings are painted Tiffany blue, and the hand-crafted chandeliers date back more than 125 years. Of course, the history doesn’t end there.

Continue to wander along the medley of narrow streets in St. Augustine, and you’ll run into pieces of the past around every corner: the Cathedral Basilica, home to the first Catholic parish in North America; Aviles Street, the oldest street in the USA; and the Lightner Museum, which boasts artifacts like a fossilized dinosaur egg and a stuffed lion that belonged to Winston Churchill.

The view from above
Ask a handful of people for their thoughts on St. Augustine, and you’ll get a mishmash of answers. For some, it’s a place of Old World allure that embraces precisely the right amount of yesteryear and modernity. For others, the focus is squarely set on the charming beach culture full of surfers, hole-in-the-wall eateries and geographic superlatives.

“St. Augustine has a wonderful energy,” says Lorelie Johnson, an Orlando resident who has visited the city twice a year since 1998. “You feel welcome when you arrive, and there’s enough to stop and enjoy, but not too much to feel overwhelmed and stressed about your visit.”

To get a big-picture view of the city, I choose to hop into a 1935 model WACO biplane around sunset. Dave Genet, owner of St. Augustine Biplane Rides, greets me with a grin. Within minutes, we strap on old-school pilot caps and taxi down the runway to relive the Golden Age of flying, open cockpit and all. We pass by the lighthouse, the Castillo and Flagler College.

When we drop to about 500 feet, I’m on the lookout for manatees, rays and sharks. Ever vigilant, I pat myself on the back for spotting a shark and teeming schools of baitfish.

As we swoop down even lower, the piece-de-resistance appears: the salt marshes, where water snakes through the neon-green grass for miles. I imagine the creatures I’d meet if I were a spoonbill gliding inches above it. Fiddler crabs, marine worms and jellyfish galore.

I thought I had a good handle on the splendor of this area, but I was wrong. It’s even more gorgeous from 1,000 feet in the air. That said, I can’t wipe the silly grin off of my face; I fully appreciate every facet around me. The puffy clouds above. The greenery below. It’s like falling into a good dream.

If you go:
Where to eat
The Beachcomber
Sit outside under the large umbrellas and chow down on oversized pancakes with all the right toppings. Afterward, stroll along the Atlantic.

The Floridian
Crowd pleasers at this farm-to-table eatery include fried green tomato bruschetta, the cornbread stack (cheddar and veggie-stuffed cornbread topped with blackened fish) and the not-your-mama’s meatloaf sandwich.

Present Moment Cafe
This organic, vegetarian café specializes in unprocessed dishes including pad thai, creamy white truffle pesto pasta and the collard wrap of the day.

What to do
St. Augustine Eco Tours
Spend some quality time learning about the surrounding ecosystem. Tours leave from the St. Augustine Municipal Marina (between the Bridge of Lions and the former Santa Maria restaurant).

Flagler College
Sign up for a historic tour and marvel at the Spanish Renaissance architecture.

St. Augustine Biplane Rides
Experience the thrill of flying in an open-cockpit biplane.

Where to stay
Casa Monica Hotel
If you’ve ever wondered what it’d be like to stay at an 1888 Moorish revival castle, here’s your chance. Part of the Kessler Collection, boasts eclectic interiors, two restaurants and an eyeful of artwork.

Casablanca Inn
This restored 1914 Mediterranean revival bed and breakfast, has sweeping views of Matanzas Bay. Grab a seat on the porch for some prime people-watching.