Words by Christine Vandyk
The pencil-sized holes in the sand are from tiny sea creatures that burrow down as the waves peel back from the shore. They’re called coquina, and half a century before the Mayflower struck Plymouth Rock, they made up the mortar of America’s oldest city. From homes and businesses to fences and the fort of Castillo de San Marcos, coquina was the rock that built St. Augustine.
In a world where every place you go seems vaguely familiar, St. Augustine is special. Oak tree branches dip beneath the weight of Spanish moss. Footsteps echo along centuries-old cobblestones. And those pastel-colored coquina shells are embedded across the landscape.
This is a place where it’s hard to imagine you’re anywhere but here.
Founded by the Spanish in 1565, the Ancient City lies at the crossroads of American history. Tucked somewhere between colonial exploration and the Gilded Age, this town on the Matanzas River has welcomed everyone from conquistadors to industrialists to northerners chasing the “winter season.” Standard Oil cofounder Henry Flagler opened the opulent Ponce de Leon Hotel in 1888, and shortly after a who’s who of presidents and celebrities partied away the turn of the century in a banquet hall lit by Tiffany glass.
Today, St. Augustine is considered a National Historic Landmark—144 blocks of Spanish Renaissance architecture and period-clad reenactors. Amidst the typical tourist trappings (alligator farms, pressed pennies, and neon-colored shirts declaring, ‘My parents went to Florida and all I got was this lousy T-Shirt’), there remains a sense of authenticity.
It’s the laid-back vibes and nonchalance that let you know the locals still run things. Flip flops and house-made spirits are the fashion of the day, and nearly everyone has a surfboard in the back of the car. It’s a city steeped in history, but it’s also chock-full of kitsch and, as of late, quite the foodie destination. If time permits, stop by during the songwriter’s festival or Nights of Lights, the Christmas Lights Display considered one of the best in the world. And as you stroll about, take note of the tiny shells sprinkled across the face of America’s first town.
St. Francis Inn
Founded in 1791, the oldest B&B in the city is located right in the heart of old St. Augustine.
Casa Monica Resort & Spa
This historic hotel was once owned by Henry Flagler. The Moorish-styled property features Moroccan frescos, ornate chandeliers, and rich tapestries.
The Collector Luxury Inn & Gardens
Falls somewhere between an intimate B&B and a luxury resort. Named one of the ten “Best New Hotels in America” by USA Today, it is a thoughtfully-designed property on a one-acre oasis in the center of the Ancient City.
Eat & Drink
O’Steen’s Restaurant and Schooner’s Seafood House
Are mainstays that keep the locals lined up for fried shrimp, area-caught redfish, and a variety of Southern fixins.
This new breed of restaurant welcomes folks to a more refined table with steak, lamb, and fresh seafood.
Ice Plant Bar
Housed in a 1927 industrial building, the popular joint boasts locally-sourced food and craft cocktails with spirits from the St. Augustine Distillery downstairs.
A vintage gastropub, bar, and live music venue that sits on the very spot where the Genovar Theater once ushered in Flagler’s prohibition era.
Located inside the Casa Monica Hotel, the Costa Brava is beloved for its breakfasts and Sunday brunch. Make sure to check out the shrimp and lump crabmeat omelet; it’s out of this world!
Mayday Ice Cream
Beat the heat with a scoop of Parent Trap ice cream. This creamy dessert is a salty peanut butter-swirled ice cream with chunks of Oreo cookies and melted peanut butter.
Mangrove Surf Shop
Surfing is king in Florida. This family-owned business offering private and group lessons will have you hanging ten in no time. You’ll also find a great selection of boards and beach apparel.
Anastasia State Park
This beachside park features 1,600 acres of unspoiled coast, tidal marshes, and hammocks. It also features some of the best waves on the East Coast, thanks to four miles of break at spots such as, “The Middles” and “North of Blowhole.”
Drifters Bike Rental
Explore the city while pedaling about the old town on a bike brought directly to your hotel.
The cobblestone streets of St. Augustine’s historic corridor are chock-full of history and fascinating glimpses into Old Florida culture. Check out the impressive collection of 19th century art housed in the former Alcazar Hotel, now known as the Lightner Museum. Pop into Flagler College, which used to be Henry Flagler’s famed Ponce de Leon Hotel, and check out the striking displays of Tiffany glass in the school’s cafeteria! Then make your way to the fort of Castillo de San Marcos to learn about those tiny coquina shells that were so strong they could withstand a cannonball.
Old Town Trolley Tours
For a comprehensive history that includes a fascinating look into the civil rights movement in St. Augustine, hop on board for all the highlights.
This is the go-to place for one-of-a-kind jewelry pieces.
West to East
A boutique known for specialty finds for the home.
Declaration & Co
A charming shop with well-curated fashions and a “homeroom” space for DIY projects and instructional classes.
Located in a quaint neighborhood along San Marcos Avenue, this homey cafe and gift shop serves up health-conscious light bites, organic coffees, and tempting baked goods.
Grab a chai latte and explore this talented artist’s collection of coastal designs. Florida citrus, salt-run oysters, and local botanicals are displayed on prints, originals, and stationery options.