Head South to Explore America’s Oldest City
Words by Jennifer Stewart Kornegay
Photos courtesy of Florida’s Historic Coast
Every summer, Southerners complain about the heat smothering the region. But come winter, plenty of Southern spots get plenty cold, bringing on a new gripe. With average November temperatures rising to 75 and with enough sunny days to ensure it lives up to its Sunshine State location, St. Augustine, Florida, beckons as a balmy escape. But this seaside getaway promises more than warmer weather. The nation’s oldest city shows off its antiquity, yet never feels stuck in yesterday, blending the allure of its past (we’re looking at you, eye-catching Spanish Colonial architecture) with its current energetic culture. And while you should check out some of St. Augustine’s best-known sites—because they’re popular for a reason—the city also contains less touristy experiences.
Old-World Character
Walk back in time along some of the oldest thoroughfares in the country, including worn brick-paved routes crisscrossing the heart of historic downtown, dubbed “Old Town,” which houses structures dating back to the 1700s, as well as numerous museums, galleries, shops, and eateries, including a few hidden gems. Search for the sign leading to the tucked-away Ronnoc’s Trading Post to find shelves filled with throwback wooden toys, rustic pottery, and other items fashioned by the owner and other local creatives. Peruse The Golden Gypsy’s eclectic and colorful selection of art, jewelry, home decor, and more. And pop into Pepper Palace to dig into a distinctive local flavor, the Datil pepper. Thriving at farms in and around St. Augustine, these little veggies pack a fiery but fruity punch, making them perfect for hot sauces and salsas. They feature as ingredients on multiple area menus, but grab a bottle or two of Datil hot sauce to take home, too.
At the Castillo de San Marcos, tour the country’s oldest masonry fort. Built by the Spanish using a seashell-studded limestone material, it sits right on the water, making it a scenic spot for a breezy walk. Just a few blocks away, a stroll amid Flagler College offers opportunities to ogle ornate Spanish Renaissance architecture. And you won’t regret spending just a little of your precious travel time at Ponce de Leon’s Fountain of Youth Archeological Park. Its powers are myth, but its appeal is real. It’s one of the oldest tourist attractions in Florida, and drinking from the iconic spring once thought to halt aging is a St. Augustine “must-do.”
Night Life
A guided evening kayak tour on saltwater Guana Lake offers nature exploration with a glow-up, thanks to billions of bioluminescent comb jellyfish and other glimmering sea creatures lighting up the water with a radiant chemical reaction. Book a paddle with GeoTrippin’ Adventure Company; the business also offers a range of other water-based eco-tours.
Shopping Stops
Several shops on the edge of Old Town and away from the crowds are well worth the short walk. Discover a rainbow of textiles, basket bags, and hand-painted woven hats from Indonesia at Coastal Traders Indonesian Imports. The vibrance continues inside Crafts Without Borders with local artisan and store owner Caroline Redding’s elaborate earrings fashioned by hand-tatting thread in a range of hues. And immerse yourself in a cornucopia of funky art, midcentury barware, vintage clothes, and retro costume jewelry at secondhand store Cool and Collected.
The nation’s oldest city shows off its antiquity, yet never feels stuck in yesterday.
Where History Happened
A bit off the beaten path, the Lincolnville Museum and Cultural Center highlights a chapter in St. Augustine’s story sometimes eclipsed by Spain’s influence on the city’s history, telling the tale of the area’s Black residents. With exhibits, art, lectures, and live programs, the Center shines a spotlight on more than 450 years of heritage and heroism, beginning with the free and enslaved Africans who traveled to the area with the Spanish in 1565 and leading up to the role of St. Augustine in the modern Civil Rights Movement. The city is also home to the first free Black settlement in the United States, which is now memorialized in Fort Mose Historic State Park. Bask in the area’s lush landscapes with an easy hike along the park’s shaded Flight to Freedom Trail, where educational signage along the way traces the harrowing journey men, women, and children made in their quest to live unencumbered.
Toes in the Sand
With so many attractions, you could forget you’re in a coastal enclave with 42 miles of shoreline fronting sparkling Atlantic waters. Don’t. Spend a few hours lounging on beautiful Vilano Beach or the wide shores of family-friendly St. Augustine Beach with its playground and splash pad.
Local Flavor
In the morning, sip some Florida-roasted coffee amid the tropical, thrift-store vibe of Spinster Abbott’s. Later in the day, belly up to the bar for some Florida-brewed craft suds on tap, or opt for a glass of bubbly draft prosecco with a stir-in of sweet, just-squeezed seasonal fruit juice.
Refreshing cocktails like the vodka-based, coconut- and lemon-infused Euphoria keep things cool at The Ice Plant, a bar housed in a former 1927 ice factory, where the decor includes giant metal ice tongs. But don’t skip the food. Fluffy blue-crab beignets with Datil pepper remoulade and shrimp soaked in a bright blend of avocado, salsa, pineapple, and crunchy pepitas make just-right lunch bites.
Taste Argentina by way of St. Augustine at Asado Life, a bustling spot turning out hearty Argentine and globally inspired dishes using South American cooking methods, like smoking, ember roasting, and live-fire grilling, and pairing them with stunning waterfront views. Standout entrees include Korean barbecue beef cheeks with pickled peppers and cilantro, and the Asado trio: grilled fresh-catch fish, shrimp, and clams swimming in a tangy tomato broth.
Sate any cocktail craving at Boat Drinks. From the cheeky cocktail names (Weekend at Bernie’s or Motorboatin’ Mule, anyone?) to the cheesy 1970s- and ’80s-era snapshots of bikini-clad babes and speedo-wearing beefcakes lacquered to the patio’s wooden bar, this spot charts a course for a good time and invites you on board for the ride.
Stay
With its curved lines and colors pulled from Florida’s sky and sea, the Hyatt Place Vilano Beach is an Art Deco-style stunner filled with modern comforts and amenities. Sand, surf, and the Vilano Beach pier are an easy walk away, and Pesca, its rooftop bar, serves panoramic vistas alongside classic and creative cocktails.
Merry & Bright
St. Augustine shines during the holidays, when its Nights of Lights set the city aglow for six weeks, starting Nov. 15. Millions of twinkling white bulbs illuminate sidewalks, treetops, and everything in between, creating a sparkling experience hailed by National Geographic as one of the world’s “top 10 lights displays.”
Take-Home Treasures
The sunken treasure room at the St. Augustine Pirate & Treasure Museum points to the city’s deep well of pirate lore, but plenty of modern booty is ready to be unearthed, too. In an alcove behind Old Town’s bustling St. George Street, Mustache: Merchant of Man-Crafts’ tiny booth boasts big scores for folks serious about their facial hair care. Grab a few tins of its herb- and botanical-based beard balms, handmade in St. Augustine. At Anchor Boutique, shop sleek, sophisticated rings, earrings, and necklaces, many designed by owner Laurel Baker. And stock up on St. Augustine aromas with Declaration & Co.’s hand-poured scented candles. Favorite sniffs include the citrusy-salty Fountain of Youth and vanilla-orange Florida Sunshine.
With so many attractions, you could forget you’re in a coastal enclave with 42 miles of shoreline fronting sparkling Atlantic waters. Don’t.
