I’ll let you in on a secret. I love to visit St. Augustine, Florida. For one, it’s a fairly easy day’s drive from my home in Virginia and, two, it has it all with incredible history, a magnificent colonial district, fantastic restaurants, fun nightlife and excellent inshore fishing.
Founded in 1565 by Spain as a military outpost, St. Augustine, Florida, is one of America’s most historic cities. For nearly two centuries, St. Augustine was the northern stronghold of Spanish conquest on the East Coast, fending off incursions by the hated English, who controlled affairs from Georgia and the Carolinas to New York.
Let’s break this July 2024 St. Augustine visit trip down into three sections, first looking at three historic forts you can tour, then checking out some of the food scene, followed by a morning fishing trip with Todd Loveday of Todd’s Rods Charters. Note: Part of this blog appeared as an article in Military Officer magazine in 2024. This is an expanded blog with lots of additional photos.
Historic Forts
Military history enthusiasts can visit three unique sites in St. Augustine.
The most impressive is the Castillo de San Marcos National Monument, the oldest masonry fortification in the continental United States. Construction began in 1672. Situated on the waterfront just a few hundred yards from the old city’s iconic gate, the fort offered townspeople refuge during attacks by pirates and the English.
Castillo de San Marcos is made of a semi-rare form of limestone called coquina, formed over centuries by decomposing small seashells. A quarry on Anastasia Island helps visitors understand how this rock was removed and transported. Coquina is light and porous, seemingly suboptimal for fortifications. Amazingly, though, its composition lets cannon balls burrow in without shattering the walls, sort of like firing a BB into a block of Styrofoam.
In 1702, British Colonial Governor James Moore of Charleston attacked, capturing the town and training cannons on the fort. The cannon balls bounced off or sunk in a few inches. Moore burned the town when he abandoned it 58 days later. Another English attack, this one by Gen. James Oglethorpe in 1740, included a 27-day bombardment. Still the fort held.
Protecting St. Augustine’s southern “back door” against marauding access via the coastal inlet and river that flows past the city, was Fort Matanzas, another coquina structure equipped with five cannons. Fort Matanzas National Monument on Rattlesnake Island preserves the fortified coquina watchtower, completed in 1742. The fort’s completion was timely, with its gunners warding off a British foray that year. They never had to fire the guns again. A ferry transports guests several times each day, except for Tuesdays, from the visitor center to the fort, with rangers offering informative tours.
France was also sparring with Spain and England for pieces of North America. In 1564, not far from where Fort Matanzas was erected, Admiral Pedro Menendez de Aviles captured and slaughtered nearly 250 French soldiers marooned there by a storm. From that time forward, the inlet and its river were named Matanzas, Spanish for “slaughters.”
A few miles north of Castillo de San Marcos is a 40-acre state historic park, close to the original site of Fort Mose (pronounced Moe-zay). In 1738, the Spanish governor chartered the settlement of Gracia Real de Santa Teresa de Mose for people fleeing slavery in the English colonies. Spanish slavery was of a different ilk than that practiced by the English and slaves escaping the Carolinas and making it to Florida could gain their freedom by declaring allegiance to Spain’s king and becoming members of the Catholic Church.
Spanish leaders might not have been entirely altruistic, for Fort Mose was situated as the northern buffer to St. Augustine proper. The Spanish also knew there were advantages to disrupting the slavery component of the British Colonial economy. Over the 25 years or so of its existence, some 100 Africans made Fort Mose their home.
A reproduction of the Fort Mose site is near completion and it is likely to be open for tours by mid-April 2025..
Fantastic Food
St. Augustine features a wondrous blend of architecture ranging from Colonial Spanish to opulent American Gilded Age. Spanish and Cuban influences abound in the vibrant local food scene.
For a curated sample of delicious dining options, consider The Tastings Tour. I spent an afternoon on a tour, riding a trolley and stopping at locations where you enjoy tapas-sized portions paired with superb wines or craft cocktails. Oh yeah, there was a bachelorette party on the tour, so, yeah...
Things kicked off at La Cocina, located on the rooftop of the San Sebastian Winery. There, we were served confit of duck with a quinoa succotash along with a glass of delicious red wine. Next, we went to The Old City House Inn, a place on one of those quintessential St. Augustine streets, oozing with character and old-world charm. The chef there served pistachio-encrusted grilled salmon with tarragon and a lemon cream sauce aside a perfect risotto. Of course, the place is said to be haunted, as are many areas of the city. A sketch of a Spanish soldier is on the wall as you enter. He is supposedly the spirit that still lives at the inn.
Decadent desserts, such as fresh peaches and cream, chocolate delight orange torts and an amazing sea salt bourbon caramel brownie starred at Bourbon and Boards, near the heart of the old city. The peaches were cooked in thyme and rosemary syrup and served alongside a white chocolate cinnamon mousse, topped with candied walnuts and fresh thyme. The brownie won first place in the dessert round of the Feast of St. Augustine competition. It is amazing. The Bourbon and Boards staff can recommend the perfect wine or bourbon to accompany the treats. Owners Troy and Melisa turned me on to an incredible bourbon called Horse Soldier, made by former Green Berets and commemorative of those early days of the Afghan war after 9/11. For a barrel strength bourbon, it was the smoothest, best I've ever had. THANKS TROY!
We wrapped up at the Carrera Wine Cellar where we had a tasting of several different wines from around the world and a charcuterie board that featured some delectable flavors to complement the wines. It was a fun afternoon.
For breakfast or brunch, it’s hard to top the Sun Day Gathering Table. Barbara Golden, my host in St. Augustine suggested we try the restaurant for an “elevated” breakfast experience. I’ll say. Try the eggs Benedict with smoked pork, or really gild the lily and add lobster.
Expanded fine dining options abound. For traditional Spanish and Cuban flair, the bustling Columbia Restaurant can be tough to beat. Making waves – and in high demand – is La Nouvelle. This French, elevated bistro style restaurant is in the beautifully adapted Jefferson House, a Victorian mansion in St. Augustine’s historic and eclectic Lincolnville area, established after the Civil War by freedmen. The 50-block district contains most of the Victorian-era homes found in St. Augustine. La Nouvelle's regular menu is inspiring, loaded with fine French entrees and appetizers, created by a chef from Marseilles. A seafood-loaded Bouillabaisse Marseillaise (a daily special when we dined), is something that I would term a "destination" dish. It was so superb. This is not a touristy, volume-dining experience. Reservations are highly recommended. Oh, and for sheer elegance with a hefty splash of culinary showmanship on your plate, check out the dessert L'Orange, created with a white chocolate shell and an orange compote and ganache. Carefully crack it open and the goodness oozes out.
Sometimes, when I’m in Florida, I just want a simple, good grilled grouper or mahi sandwich, preferably somewhere near the water. On my last night in town, I headed down the A1A to St. Augustine Beach, looking for a legendary restaurant/bar called the Oasis, a double-deck setup with restaurant downstairs and a bar with live music upstairs. It’s not exactly “on the water,” but there was a thunderstorm going on so at least I got wet. Dining alone, I ate at the counter, facing the kitchen. The grouper sandwich was worth the drive – a huge slab of perfectly cooked fish with tasty fries and a locally brewed Matanzas Red Ale. .
Go Fishing!
It is always a great day when I get to go fishing - doubly great when my granddaughter McKayla makes time to head out on the water with me. She has been fishing with me from boats, canoes and shore since she was a toddler. She arrived in St. Augustine in mid-afternoon. We immediately set out to do a little sightseeing, visiting the historic St. Augustine Lighthouse and museum. Yes, the lighthouse and adjacent building is said to be haunted. McKayla scampered up the circular staircase to the observation deck while I ventured next door, to the home where the lightkeepers lived. I visited here a few years ago, as work was ongoing on exhibits in the basement. I recall stepping off the last step to the basement floor and feeling my pant leg getting distinctively grabbed and held – like I said, haunted. No spooks this time, though. Happily. Some people say you can smell pipe smoke wafting through the lighthouse at times.
From there, we headed downtown and made a hurried sweep through the fun and educational Pirate Museum in the Historic District. We only had time for a quick dinner before rendezvousing with a group heading out for a ghost tour of the city. Ghost tours can be all over the board in terms of the information, the stories and the experience. This one was pretty good, but you better make sure you’ve got some comfortable shoes because it’s a hike. Interestingly, one of the places we ended up at was Castillo de San Marcos. Our ghost guide walked us around the perimeter, stopping at a wall that had hundreds of pock marks in it, most about the height you’d associate with the height of a grown man. Here is where they executed people by firing squad, we were told. Now, I have no idea if this is true, and I never followed up with any legitimate historian to find out. I do know that the firearms that would’ve been used during that period were clunky, low velocity weapons. Some of the marks were a couple feet high and some were down around the ankles. The soldiers must’ve aimed high, had squibs or missed a lot at close range. If I research this more, I’ll update this blog.
The next morning, we fished with Capt. Todd Loveday (Todd's Rods). He grew up in the area and has been an avid angler since he was a kid. A few years ago, he traded his day job to become a full-time fishing guide. He was always a successful flounder tournament competitor. When he says he knows where the redfish and flounder like to go under certain conditions, he means it. We only booked a five-hour trip, but it took just a couple of stops to find the honey hole. McKayla and I were using new lures made by Snapper Slapper, basically squid-shaped jigheads with a skirt and a good, sharp hook. The one-ounce lure with the white skirt and red band around the jighead was seemingly irresistible. We caught multiple species of fish on the lure, from chunky top-of-the-slot limit redfish to quality flounder. We even caught a bonnethead shark and a small jack crevalle.
After the fishing was done, Todd pulled a large cutting board from his truck and cleaned our catch right there on the tailgate, using a new Smith’s 7-inch-blade fillet knife. Todd expertly used the knife to fillet a flounder so cleanly that you could see thought remaining bones and tissue. Naturally, the payoff continued as McKayla and I both dined on fresh fish fillets for a few days.
The trip was a bit of a whirlwind, but it's doable. Give St. Augustine a look next time you're planning a Florida vacation.
Visit St. Augustine
*Castillo de San Marcos: Open daily, except Christmas, from 9 a.m. to 5 p.m. Exterior ground open until midnight. Standard adult admission $15, but several passes, including military, are honored and afford free admission. Living history reenactors routinely perform, sometimes issuing the order “Fuego” and firing cannons. Weekdays are least crowded.
*Fort Matanzas: Free access, including ferry to the fort. Ferry tickets only available at the fort’s visitor center. No ferry service on Tuesdays.
*Fort Mose: Free. Visitor center open 9 a.m. to 5 p.m., Thursday through Monday. A replica of the fort is near completion and likely to be open for tours by mid-April.
*For a full lineup of fun, interesting, delicious activities, lodging options and more, see www.floridashistoriccoast.com.
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