St. Augustine Then and Now

A look at St. Augustine's founding and the destination today as the city celebrates its 450th anniversary.

Seeing St. Augustine from the Bridge of Lions for the first time is like peering through the keyhole of a centuries-old treasure chest. The majestic towers of Flagler College and the Lightner Museum pierce the blue sky while sailboats bob on Matanzas Bay below. In this small and picturesque city by the sea, narrow cobblestone streets overflow with sightseers, and bay front taverns spill with revelers. It’s difficult to tell who’s a local and who’s a tourist. The travelers make themselves right at home, and the natives never grow tired of their hometown sites and their proud place in history as the oldest permanent European settlement in the United States. This year, local pride is stronger than ever, as the city commemorates its 450th anniversary and plans a big birthday bash, complete with a visit from the pope, the king and queen of Spain, a wine festival, tall-ship visits, historical reenactments and special exhibits.

“We’re home to the first settlement, the first free-black settlement, the first school system, the first library, the first port,” says Davis Walker, president of Florida Living History, which performs historical reenactments around the state. “Florida has the most unique, most interesting and the longest history in the nation, yet it’s also the least known. U.S. history has been consciously distorted. The country was settled from South to North and not from North to South.”

Map of St. Augustine and Fort Mose

“Half a century before the Pilgrims landed at Plymouth, we had 120 houses, a tavern, wine and beer making, a fish market and churches,” adds Dana Ste. Claire, director of St. Augustine’s 450th commemoration committee.

Florida’s Founding

In April 1513 explorer Ponce de León landed near St. Augustine, staking a claim for the Spanish crown. While he did not establish a settlement, he sent word back that Florida was an ideal place for a colony. Fifty-two years later, Pedro Menéndez de Avilés left Spain under direction of the king to establish a string of settlements on the eastern seaboard, starting with St. Augustine in 1565.

“We were ground zero for the American melting pot,” says St. Augustine Mayor Joe Boles, a 47-year resident of the city. “When Menéndez got off the boat, he had with him both free and enslaved Africans, French, Italian and five Hispanic groups. Visitors can experience the very genesis of America right here. St. Augustine is very European in character and flavor and is a blend of cultures that can be traced back to 1565.” 

In the early days, tensions ran strong between Spain, France and England for their place in the New World, and the Spanish settlement of St. Augustine suffered from many attacks. The first pirate attack was by Sir Francis Drake in 1586 who nearly demolished the settlement, and following another massive attack in the 17th century, Queen Mariana of Spain had the Castillo de San Marcos built to protect the city. The Spanish built the massive fort from the area’s plentiful coquina shells, a material so strong, it actually absorbed the blasts of cannonballs. The strength of the fort, paired with the help of the Timucuas, allowed St. Augustine to persevere when other Spanish settlements failed. The fort stands today as a symbol for the city. 

Castillo de San Marcos in St. Augustine, Florida

A Resort Community

In the 1880s, American businessman Henry M. Flagler, who co-owned Standard Oil with John D. Rockefeller, saw great tourism potential for St. Augustine. He built two luxury hotels, the Ponce de Leon and the Alcazar, and he purchased the Jacksonville, St. Augustine & Halifax Railroad to link his properties with other destinations. Flagler hired John Carrère and Thomas Hastings, designers of the New York Public Library, as architects. The Hotel Ponce de Leon featured an 80-foot domed ceiling with 79 stained-glass windows by Louis Comfort Tiffany—son of the famous jeweler—and hand-painted murals on the walls and ceiling by renowned artist George Maynard. Among the famous guests were Theodore Roosevelt, Joseph Pulitzer, Mark Twain and Babe Ruth. Flagler also sold land to architect Franklin W. Smith who built the nearby Casa Monica Hotel, which is the only of the three properties used as a hotel today. The Hotel Ponce de Leon became the home of Flagler College in 1968, and the Alcazar now houses the Lightner Museum. 

Flagler College, the former Ponce de Leon Hotel

St. Augustine Today

St. Augustine remains a relevant and fresh travel destination today with 6 million tourists, 13,000 locals and 7,000 students and has received accolades from the likes of Coastal Living, USA Today and Smithsonian.

Flagler College, St. Augustine

In the 1700s, St. Augustine was home to 40 taverns. But long gone are the sailors sloshing cheap beer and rum. Today’s visitors share sangria and tapas at the Taberna Caballo in Colonial Quarter, college students take advantage of happy hour at Meehan’s Irish pub on the bayfront, and young professionals sip hand-crafted cocktails made with locally distilled vodka at the Ice Plant. Area chefs play homage to the history by giving traditional recipes a modern twist. Everyone from tiny, Spanish bakeries to oceanfront seafood shacks and elegant dining rooms in Victorian mansions are serving up innovative cuisine that’s both thoughtful of the past yet on trend today. St. Augustine has its own brewery, its own winery and a Spanish market offering imported goods like Manchego cheese, Iberico ham, olive oils and chorizo sausages. Foodies here will find a melting pot of Southern, Spanish, Caribbean and Floribbean cuisine featuring local seafood and farm-fresh produce. 

 Local vodka at The Ice Plant in St. Augustine

Chef Michael Lugo of the Tasting Room, whose family hails from Puerto Rico, feels a connection with the Spanish heritage. “We get inspired by the history, yet we always want to recreate it in a sense,” he says. Lugo makes paella fritters as tapas and uses Florida orange juice and local datil peppers and shrimp for the Spanish favorite, gambas al ajallo

After getting a taste of the city, visitors can visit more than a dozen historic sites from the lighthouse to the castillo or admire the sites from a trolley or horse-drawn carriage. Just south of the Plaza de Constitution is Avilés Street, the nation’s oldest platted street, dating to 1573. The narrow, quaint street is lined with sidewalk cafés, local shops and art galleries and an antique store that’s said to be haunted. Nearby is St. George, another charming corridor through the heart of the city’s historic core. 

Ponte Vedra beach in St. Augustine

With all the history, visitors should be sure to leave time for the beaches. Driving up AIA toward Ponte Vedra, on the right the Atlantic Ocean is just feet from the car window, and to the left, the scruffy and dense palmetto forest separates the road from the Intracoastal Waterway — surely arduous for early explorers, yet beautiful in its wildness today. Pull into the public lot at Mickler’s Landing, and take the boardwalk out to the beach. Watching the sunrise on the Atlantic and leaving the day’s first footsteps in the sand is an amazing, godly feeling, much like the Spanish explorers must have felt when coming ashore way back then.