Road tripping south on U.S. Route 1 is not unlike journeying along any other major corridor of America’s vast highway system. The mile marker numbers dwindle down while glowing golden arches and red triangles crop up, blazing bright in attempts to lure travelers to “eat here,” “fill up here,” “stay here.” Eventually, the Interstate meanders into St. Johns County, Florida, and cuts through the city of St. Augustine.
You’ll notice the street sign has changed—you’re now on North Ponce de Leon Boulevard—but really, the entire scenery has shifted just a bit. Gleaming stone structures with sawtooth crowns and burnt orange scales of clay tile roofing jut against the skyline; ornate, gilded towers and church steeples loom higher still, appearing as if a pair of giant hands pinched their spires and tugged upward until each exquisite joint had unfolded. None of this should come as any surprise. You are in the oldest city in the United States.
Yep, everything you learned in high school history has been a lie. Long before the ink had dried on the Declaration of Independence, even before the English settled Jamestown, the Spanish had already laid claim to St. Augustine in 1565. Along with the rest of Florida, the territory changed hands several times over the centuries, caught in a tug-of-war between warring powers— Great Britain, Spain, the United States—who either saw the state as an ally or an annoyance. Perhaps unintentionally, St. Augustine became the physical expression of its multicultural biography, a layered narrative imprinted through ancient architecture, infused cuisine, and, yes, even a few restless specters that roam after dark. Like the many side roads that flank the lively St. George Street, there’s more than one path to discovering St. Augustine.
OLD WORLD ATTRACTION // Similar to Boston, Charleston, and cities of that ilk, one of St. Augustine’s primary attractions is the preservation of its rich, diverse history. While the age of Spanish conquistadors, pirates, and “father” of St. Augustine Henry Flagler is since bygone, the past remains an active facet of the everyday. A simple stroll down St. George Street—surrounded by stone buildings dyed in muted hues of splashy colors and broad balconies suspended over worn, pedestrian-only pathways—is an immersive encounter with some of St. Augustine’s oldest edifices. Five minutes away, the former Hotel Ponce de Leon is now home to Flagler College, a Spanish Renaissance– style property distinguished by its intricate, exquisite carved moldings, courtyard fountain, kaleidoscopic Louis Comfort Tiffany stained-glass windows, and brilliant, hand-painted gold leaf ceiling art.
If you like the smell of gunpowder and things that go boom, an afternoon at the Castillo de San Marcos fort is worth the $10 entrance fee—and possible sunburn, depending on what time of year you choose to visit. Initially constructed by the Spanish in the latter half of the seventeenth century using small, crushed shells known as coquinas, the 320-acre fort was officially designated as a U.S. National Monument in 1924. Visitors flock by the thousands each day to learn about the fort’s bloody, layered history, explore the numerous intact interior rooms, and observe one of the park’s thrilling cannon firings held Friday through Sunday, a unique experience made complete with full colonial-era dress and a fiery explosion over the Matanza River.
Cross the A1A bridge onto Anastasia Island, and you’ll find the St. Augustine Lighthouse & Maritime Museum, a still-functional beacon that was recently restored after fire and other natural disasters devastated the centuries-old landmark. Ribboned in classic black-and-white with a ruby red–domed lantern room, the lighthouse beams proudly over Florida’s Salt Run waters, 165 feet high with 219 steps to match. Give the spiral staircase a go and you’ll be rewarded with an incredible panorama of the area’s natural assets: lazily swaying treetops, sinuous rivulets of sea, whiffs of salt air. When you start to feel tired on step 168, remember: lighthouse keepers used to carry 30 pound drums of oil up here. No. Excuses.
CONTEMPORARY CHARM // So we’ve established that St. Augustine has history—and lots of it. However, one thing the city continues to do well is find new ways to escort the past into the modern age.
Take the St. Augustine Distillery, for example. Following a massive overhaul a few years back, the once crippled, dilapidated Florida Power and Light Ice Plant Company has found a new spirit, well, making spirits. Brewed, barreled, and aged using native ingredients from local farmers (and that famous Florida humidity), the St. Augustine Distillery is the first family of bourbon in the Sunshine State. After a free tour of the distillery’s small-batch operations—be sure to ask about Bertha—visitors get a chance to sample the wares, a collection of firewater that includes rum along with award-winning vodka and gin recipes. If you’re real agreeable, the bartender might mix up one of their signature Florida Mule cocktails. Just watch out—this mule kicks.
It’s easy to miss the Casa Monica Resort & Spa if you’re not sure where to look. The Kessler Collection hotel was, after all, renovated to blend in with its storied environment, shedding its skin as a standard government building in favor of a rooftop pool deck, lavish, Moorish Revival interiors, and founder Richard Kessler’s well-trained eye for a good piece of art. That first step into the hotel lobby feels like a step into a different part of the world, let alone a different time frame altogether. Throne arm chairs with plush cushions in royal colors stand at attention; opulent Moroccan sconces dangle overhead, their crimson glow cast over delicate calligraphy patterns that adorn the columns, shapely arched entryways, and trim; at the center of it all, a mosaic tile fountain churns peacefully. It’s a motif that carries into the hotel’s guest rooms, where velvet headboards and palettes of red and gold exude exotic regal sophistication. Casa Monica boasts twenty-first-century amenities, full-service luxuries of the Poseidon Spa, and exclusive access to the private Serenata Beach Club on nearby Ponte Vedra Beach. Not bad for a building that’s nearly 130 years old.
But like St. Augustine itself, Casa Monica’s true treasure is its timelessness, decades of people, events, and things that have since become a part of the landscape, clicking into place like a puzzle piece. And you’re invited to be a part of it.
/// Casa Monica
First constructed as a high-class resort for the elite back in the nineteenth century, the Casa Monica was restored to its former glory (and its former name) as a Kessler property in 1999. Aside from its palatial lodgings and on-site comforts, the Casa Monica is also located within walking distance of the majority of St. Augustine’s downtown attractions.
95 Cordova St, St. Augustine, FL. (904) 827-1888, casamonica.com
/// The Floridian
This casual neighborhood eatery offers modern takes on Southern favorites, including buttermilk biscuits with braised pork belly, cornflake-encrusted fish catches, meatloaf sandwiches, and shrimp po’ boys.
72 Spanish St, St. Augustine, FL. (904) 829-0655, thefloridianstaug.com
/// Costa Brava
The Casa Monica’s in-house dining experience melds together Mediterranean and Asian-influenced fare crafted by Chef Fred Mero. We recommend the quiche Lorraine.
95 Cordova St, St. Augustine, FL. (904) 810-6810, casamonica.com
/// St. George Street
Lined with an assortment of gift shops, art studios, fine dining, museums, boutiques, and watering holes, this historic downtown street has a little bit of everything to sate the St. Augustine sightseer’s appetite. If anything, go to check out the diverse, Spanish colonial architecture.
St. George St, St. Augustine, FL.
/// Lightner Museum
Once the site of Henry Flagler’s famed Hotel Alcazar, the Lightner Museum now takes up residence on three floors of the striking Spanish-style building. Its eclectic exhibits—the lifelong hobby of newspaper publisher Otto Lightner—include Victorian-era machinery, oil paintings, furniture, shrunken heads, instruments, and other unusual artifacts.
75 King St, St. Augustine, FL. (904) 824-2874, lightnermuseum.org