St. Augustine, founded in September 1565 by Don Pedro Menendez de Aviles of Spain, is the longest continually inhabited European-founded city in the United States – more commonly called the "Nation’s Oldest City."

Menendez was sent to the New World by King Philip II of Spain, with missions to rid Florida of the French and establish fortified Spanish settlements along the coast. He founded St. Augustine as his base.

In fact, many historians believe that the first Thanksgiving was a feast in St. Augustine. Some 50 years before the pilgrims broke bread with the Wampanoags in Plymouth, Mass., Spanish colonists sat down for a meal of shellfish, alligator, tortoise and wild turkey with members of Florida’s Timucua tribe.

A visit to St. Augustine, less than an hour south of Jacksonville, reveals more than four centuries of history that owes much to the Spanish, English, Greeks, African Americans and Native Americans.

Here are just a few of the highlights to be experienced in America’s oldest city:

Castillo de San Marcos
Perhaps the fort’s air of authority comes from the Castillo’s sheer size. The building’s shell alone is as big as a city block, and its site occupies more than 20 acres along the downtown corridor. Nowhere else in Florida can you see, feel and comprehend the critical role played by this little city during the years when West European countries battled each other over the Atlantic Coast in the New World. Inside the fort, visitors can investigate the many rooms of the fort’s first level—including a chapel and a single cell used as the city’s first jail—and see a video about the Castillo’s significance. But the true wonder of this fort can be experienced on the second level, where expansive views of St. Augustine, up-close looks at the towers where soldiers once stood guard and cannon demonstrations bring the fort to life.

Fort Matanzas
Almost 70 years after construction started on the Castillo, the Spanish decided the fort, which had long protected St. Augustine, needed protection itself. Construction on Fort Matanzas, built at the Matanzas inlet to block the southern approach to St. Augustine, was completed in 1742. Fort Matanzas is 50 feet on each side with a 30-foot tower—considerably smaller than the Castillo. Its remote location meant soldiers rotated in for 30-day tours of duty. Today, the site remains remote; visitors must take a free ferry to the fort’s home on Rattlesnake Island, and boarding passes for the ferry are issued from the downtown Visitor Center on a first-come, first-served basis. To get the soldiers’ birds-eye view, visitors climb a ladder to reach the roof. Archaeological surveys at Fort Matanzas have shown that the area was used, most likely as seasonal hunting camps, by Native Americans for several thousand years before the Spanish arrived.

Fort Mose Historic State Park
In 1738, the Spanish governor of Florida offered freedom to runaway slaves from the British colonies who were willing to convert to Catholicism. Many of the former slaves settled in a community north of the city called Fort Mose (mo-ZAY), making it the first legally sanctioned community of free blacks in what would become the United States. Fort Mose also had a military role, as St. Augustine’s northern defense against invading British, and saw action against invading troops in the Battle of Bloody Mose in 1740. Today, though no structure remains, the site is a Florida state park, and visitors can tour a small museum and roam the grounds.

Lightner Museum
Built in 1888 by railroad magnate Henry Flagler, the museum—formerly the Alcazar Hotel—will transport you to the Gilded Age with its stunning entrance, exquisite event spaces and one of the country’s best collections of 19th-century art.

Lincolnville Museum and Cultural Center
Housed on the site of St. Augustine’s first African American public high school, the Lincolnville Museum and Cultural Center features exhibits, artifacts, art and stories that highlight the African roots that helped shape the Ancient City, and boasts a steady stream of events. One is its Emancipation Day Re-enactment, which celebrates the saga of formerly enslaved African-Americans who settled the community of Lincolnville following the signing of life-changing legislation in 1863. It also hosts Lincolnville Jazz at the Excelsior, a concert series that showcases jazz from its African roots to the fusion sounds of the millennia.

Ponce de Leon's "Fountain of Youth"
Take a sip from Ponce de Leon’s “Fountain of Youth,” a natural spring on a privately-owned, 15-acre park in St. Augustine where visitors can learn about the first Spanish settlers. There’s a working archaeological dig on the site, along with recreated Spanish and Timucuan Indian buildings, an old mission church, cannons and a watch tower.

Oldest Wooden Schoolhouse
Jesse Fish, a land broker representing the property interests of the fleeing Spanish officers and residents after the British took possession of Florida, sold the home to Juan Genopoly, a Greek carpenter from Mani, on Oct. 1, 1780. A homestead was established and maintained by the Genopoly family for more than a century. A home built at the location in the early 1800s stands today. The main room on the ground floor was the classroom. Another, smaller room was added to the floor plan to serve as the family sitting room, with a back door for easy access to the kitchen, which is a detached building made of wood siding and a coquina chimney. The garden area behind the home was used to grow vegetables, fruits, herbs and spices. Water for cooking and drinking and water was pulled from the old well adjacent to the home.

The Old City Gate
Built in 1808 as a defense, the gate marks the north end of St. George Street. The stout coquina pillars and wall promise a unique photo opportunity. 

St. George Street and nearby
St. George Street also offers attractions, including the Medieval Torture Museum, which promises to “transport you back in time hundreds of years to some of the most miserable moments in human history.” The museum highlights methods of medieval torture through displays, props, and mannquin; while it’s fascinating and unique, it’s not for kids or those prone to nightmares.

Save time for areas close to St. George Street. Hypolita Street, Cuna Street, Cathedral Place and King Street are home to still more shops and restaurants, particularly near Casa Monica Hotel, a magnificent structure with a storied past.

If you’re looking for a quieter alternative, Aviles Street, which holds bragging rights as the oldest street in the United States, features a quaint neighborhood complete with cobblestone streets, highlighted with shops, cafes, historic sites, and galleries chock-full of original art.

You don’t need to just let your feet do the walking: other ways to tour the city include an idyllic horse-drawn carriage ride or the popular trolley.

Ghost Tours
With its years of tumultuous history, it’s hardly surprising St. Augustine is one of the most haunted cities in the country. Numerous guided ghost tours illuminate its past—who knows what you’ll see or hear on these spine-tingling adventures?

Head just out of town to explore 42 miles of pristine Atlantic beaches, where you can swim, surf, or just kick back on the sand.

While you’re there, make sure to visit the historic 1874 St. Augustine Lighthouse, a stately black and white sentinel at the nation’s oldest port. If you want to feel the burn and snag a unique view of the area at the same time, you can climb the 219 steps to reach the observation deck of the 165-foot-tall Lighthouse. Hands-on exhibits, daily programs, and nature trails round out the fun.

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