Creepy animatronics in America's oldest wooden schoolhouse. Coquina walls and canons outside of the Castillo de San Marcos. The necklace I begged my dad to get me from a jewelry vendor during a field trip.
These are the things that used to come to mind when I thought of St. Augustine, the oldest city in the country, sitting right there on the east coast of Florida about 3 ½ hours from the Tampa Bay area.
Growing up in Orlando, it was a rite of passage field trip destination, a journey all fourth-graders took. I have visited a couple of times since then, with family, in college, mostly weekend or Christmastime trips that included visits to the Ripley's Believe It or Not Museum and a couple of loops on the trolley tour.
Never did I think what I thought on my most recent trip a couple of months ago: Wow, this place is hip.
As with many places, St. Augustine's increasing cool factor is tied to its food and drink scene, which has grown notably in recent years. And Labor Day weekend is an ideal amount of time to explore the town that dates back to the 1500s. Three days, two nights, a dozen chances to nosh.
Consider a bed and breakfast for your stay, an easy way to make sure you are well-fed during the trip. They can be more affordable than you'd think, or at least in line with other hotels in the area.
After rave reviews from a couple of family members, my husband and I opt for the Cedar House Inn, where rates start around $170 depending on the time of year. It's tucked away on a street lined with other bed and breakfasts, near the Lightner Museum and Flagler College, and owned by a woman named Cyndi who will happily help plan your trip — and offer you complimentary cookies — if that's what you want. We quickly discover that the St. Augustine core is much smaller than it looks on a map, and we're a close walk to just about everything, in multiple directions.
We set out, hungry for lunch, and find ourselves at the Floridian. The relatively health-conscious lunch and dinner spot is in a charming bungalow off the recently spiffed-up Spanish Street. (Another solid lunch option: Present Moment Cafe, a cozy all-vegan spot with raw and gluten-free options.)
The menu ranges from biscuits with pork belly to a handful of salads each more alluring than the next. I get the Southern Chop Chop, a well-chopped salad with collards, peaches, candied pecans, red onion, carrots, house queso fresco, preserved lemon and shaved radishes (with chicken, $14); my husband goes for the healthified Burrito Fresco, pulled chicken in a whole wheat tortilla with quinoa, greens, salsa and datil-chipotle mayo ($13.50). Drinks come in mason jars; the decor is eclectic in a very Florida way.
Spanish Street is parallel to St. George Street, the pedestrian-only thoroughfare you've probably traversed if you've visited St. Augustine, so this is a good chance to walk off your lunch among the tourists. Dragonflies Handcrafted Jewelry and Kilwins Chocolates make for a sweet double header. Pop into Kernel Poppers and brace yourself for an overwhelming number of popcorn flavors. We spend too long staring slack jawed at the dozens of options, from birthday cake to caramel sea salt to beer cheese soup.
When you've had enough walking, set your mind on a happier hour. Our bed and breakfast is the halfway point between St. George Street and the other side of downtown, where you'll find the San Sebastian Winery. There are free tours daily, but the roof is where you want to be by about 7 p.m., when the sun begins to go down. It's a wine and jazz bar known as the Cellar Upstairs, featuring live musicians nightly and a bar that serves libations made downstairs. The Vintners Red and the Rosa (both $5) are sweet refreshments on a warm evening.
There are light appetizers if you need to nibble, but tonight is a good night to go all out at Preserved, a fine dining restaurant that opened in 2016 in the up-and-coming historic district of Lincolnville. If you ask around about where to eat while you're in town, you'll hear about this place a lot. It's housed in a Victorian-style building (called the Jefferson House, because it used to be the home of Thomas Jefferson's great-granddaughter) with a welcoming front porch and homey vibe that extends to the attentive yet not pushy waitstaff.
This was the best meal of our trip, top to bottom. After an appetizer of Tomato Tartare ($9), an exquisite play on beef tartare that tastes like a really decadent bruschetta, we order two entrees: the Lamb Tenderloin ($32), with sweet pea puree, confit carrots, asparagus, corn, field peas and a pommery mustard vinaigrette; and the Bone-in Porkchop ($26), with braised cabbage, apple, fingerling potatoes and a pommery mustard cream. It's one of those meals where you know you're too full to go on but must do so anyway because everything is so good.
After a day of eating, take it easy this morning. Full of breakfast from the Cedar House Inn, we head over the Bridge of Lions to Anastasia State Park, where you can surf the mighty waves of the Atlantic Ocean.
Back in town, lunch is a grazing affair. In a quest to find the best pizza slice, my husband tries the pies at Pizzalley's and Pizza Time, the latter declaring itself the second best pizza place in the United States. That may not be wrong. This is the clear winner in the pizza wars. There is often a line out the door, and Pizza Time only takes cash, but these large slices of New York-style pizzas are among our most memorable bites of the trip.
From there, we make our way to the St. Augustine Distillery, located in a restored ice plant from the early 1900s. Opened in 2014, this is clearly another buzzy spot . It's not hard to see why. Free tours are offered every half-hour, and they end with a tasting of four cocktails made with each of the distillery's main spirits: vodka, gin, rum and bourbon. The gleaming gift shop makes leaving empty-handed a challenge.
When you're done with all the sampling, head upstairs to the Ice Plant for elaborate cocktails and a solid menu of New American fare.
True to its name, the most interesting thing here is the ice; a mission statement on the website explains the commitment "to the craft of ice harvesting by freezing purified water in large blocks." The cocktail menu includes diagrams that detail the kinds of ice shapes that go into different drinks, which helps the bartenders control the temperature of the drinks and the "desired amount of dilution."
We order a couple of drinks at the bar before our meal, to better watch all this ice crafting in action. My drink, a green gin concoction, is chilled with ice then strained; my husband's, a rum cocktail flavored with curry powder, is served over a mountain of crushed ice. (Happy hour is from 3 to 6 p.m. Monday through Friday and 10 p.m. to 2 a.m. every day, with six classic cocktails for just $4.)
At this point, food is necessary. We split the Half Pound Ice Plant Burger (Wagyu beef, field greens, Muenster cheese, aioli, pickled green tomato, $15), fries with a truffle Parmesan sauce ($6) and the Spring Salad "Verte" (lettuce, English peas, asparagus, avocado, a seven-minute egg, smoked bacon and green goddess dressing, $13).
There is more fun to be had back toward the water. Stroll past Flagler College, down King Street and toward the Bridge of Lions, and you'll find A1A Ale Works, an ideal spot to while away the rest of the night with live music and craft beer.
It's time to head home, but not without a late-morning stop at Relámpago Coffee Lab for small-batch coffee made with locally roasted beans, and the Maple Street Biscuit Company, where you'll find dozens of menu items all built around flaky biscuits made in-house. You can't go wrong with any of the fried chicken or egg biscuits, like the Farmer (fried chicken, bacon and cheddar cheese topped with apple butter), or the house-made jellies in a variety of flavors.
From there, we head out the Old City Gates at the top of St. George Street and to the Castillo de San Marcos for some fourth-grade field trip nostalgia. And after a quick stop at the Hyppo Gourmet Ice Pops, the original location of the shop that now has locations in Tampa Bay, we hit the road, but not without a list of meals and bars we're eager to try the next time we come back.