Invasions by pirates and enemies of Spain

Succeeding governors of the province maintained a peaceful coexistence with the local Native Americans, allowing the isolated outpost of St. Augustine some stability for a few years. On May 28 and 29, 1586, soon after the Anglo-Spanish War began between England and Spain, the English privateer Sir Francis Drake sacked and burned St. Augustine. The approach of his large fleet obliged Governor Pedro Menéndez Márquez and the townspeople to flee for their safety. 

When the English got ashore, they seized some artillery pieces and a royal strongbox containing gold ducats, the garrison payroll. The killing of their sergeant major by the Spanish rearguard caused Drake to order the town burnt.
In 1609 and 1611, expeditions were sent out from St. Augustine against the English settlement at Jamestown, Virginia. In the second half of the 17th century, unsettled groups of Indians, forced southward by the expanding English colony in Carolina, made raids into Florida and killed the Franciscan priests who served at the Catholic missions. Requests by successive governors of the province to strengthen the presidio’s garrison and fortifications were ignored by the Crown.

The charter of 1663 for the new Province of Carolina, issued by King Charles II of England, was revised in 1665, claiming lands as far southward as 29 degrees north latitude, about 65 miles south of the existing Spanish settlement at St. Augustine.The English buccaneer Robert Searle then sacked St. Augustine in 1668, killing sixty people and pillaging government buildings, churches and houses, after which his pirates ransomed off some of their hostages and sold others into slavery.
This raid and the establishment of the English settlement at Charles Town spurred the Spanish monarchy to finally acknowledge the threat represented by the new English colonies to the north and strengthen the city’s defenses. In 1669, Queen Regent Mariana ordered the Viceroy of New Spain to disburse funds for the construction of a permanent masonry fortress, which began in 1672.
The Castillo de San Marcos was completed in 1695, not long before an attack by Governor Moore’s forces from Carolina in November, 1702.
Failing to take the fort after a siege of 58 days, the British troops burned St. Augustine to the ground as they retreated. In 1740, the town was again besieged, this time by the governor of the British colony of Georgia, General James Oglethorpe, who was also unable to take the fort.

Loyalist haven under British rule

The Treaty of Paris (1763), signed after Great Britain’s victory over France and Spain during the Seven Years’ War, ceded Florida to Great Britain and consequently St. Augustine became a Loyalist haven during the American Revolutionary War. The second Treaty of Paris (1783), which recognized the independence of the former British colonies north of Florida, also ceded Florida back to Spain, and as a result many of the town’s Spanish citizens returned to St Augustine. 

many of the town’s Spanish citizens returned to St Augustine. Refugees from Dr. Andrew Turnbull’s troubled colony in New Smyrna had fled to St. Augustine in 1777, and made up the majority of the city’s population during British rule. This group was (and still is) referred to locally as “Minorcans”, even though it also included settlers from Corsica, Italy and the Greek islands as well.

Second Spanish Period

During the Second Spanish Period (1784-1821) of its rule in Florida, Spain was dealing with invasions of the Iberian peninsula by Napoleon’s armies in the Peninsular War, and struggled to maintain a tenuous hold on its colonies in the western hemisphere as revolution swept South America. 

The royal administration of Florida was neglected, as the province had long been regarded as an unprofitable backwater by the Crown. The United States, however, considered Florida vital to its political and military interests as it expanded its territory in North America, and maneuvered by sometimes clandestine means to acquire it. 

The Adams–Onís Treaty, negotiated in 1819 and concluded in 1821, ceded Florida and St. Augustine, still its capital at the time, to the United States.

Territory of Florida

Florida remained an organized territory of the United States until 1845, when it was admitted into the Union as the State of Florida. The Territorial Period (1821-1845) was marked by protracted wars with the Creek Indian groups who occupied the peninsula, collectively known as “Seminoles”, during the Second Seminole War (1835-1842). The United States Army took command of the Castillo de San Marcos and renamed it Fort Marion after General Francis Marion, who fought in the American Revolutionary War.

Civil War

Florida joined the Confederacy after the Civil War began in 1861, and Confederate authorities remained in control of St. Augustine for fourteen months, even though it was barely defended, and in spite of the Union blockade of shipping off the coast. Union troops occupied St. Augustine in 1862 and controlled the city through the rest of the war. Its economy already devastated, many of the town’s citizens fled.

Henry Flagler and the railroad

Henry Flagler, a co-founder with John D. Rockefeller of the Standard Oil Company, spent the winter of 1883 in St. Augustine and found the city charming, but considered its hotels and transportation systems inadequate.

He had the idea to make St. Augustine a winter resort for wealthy Americans from the north, and to bring them south he bought several short line railroads and combined these in 1885 to form the Florida East Coast Railway. He built a railroad bridge over the St. Johns River in 1888, opening up the Atlantic coast of Florida to development.

Flagler began construction in 1887 of two large ornate hotels, the 540-room Ponce de León Hotel and the Hotel Alcazar, and bought the Casa Monica Hotel the next year. His chosen architectural firm, Carrère and Hastings, radically altered the appearance of St. Augustine and gave it a skyline, beginning an architectural trend in the state characterized by the use of elements of the Moorish Revival style. With the opening of the Ponce in 1888, St. Augustine became the winter resort of American high society for a few years.

After Flagler’s Florida East Coast Railroad had been extended southward to Palm Beach and then Miami, the rich mostly abandoned St. Augustine in the early 20th century and began to customarily spend their winters in South Florida, where the climate was warmer and freezes were rare. St. Augustine nevertheless still attracted tourists, and eventually became a destination for families traveling in automobiles as new roads were built and Americans took to the road for annual summer vacations. The tourist industry soon became the dominant sector of the local economy. With the help of state and federal government monies, St. Augustine began a program in 1935 to preserve thirty-six surviving colonial buildings and reconstruct others that were gone.

Modern St. Augustine

In 1965, St. Augustine celebrated the quadricentennial of its founding, and jointly with the State of Florida, inaugurated a program to restore part of the colonial city. When the State of Florida abolished the Historic St. Augustine Preservation Board in 1997, the City of St. Augustine assumed control of more than thirty-six buildings that had been reconstructed or restored to their historical appearance, as well as other historic properties including the Government House. In 2015, St. Augustine celebrated its 450th year of its founding with a visit from Felipe VI of Spain and Queen Letizia of Spain. On October 7, 2016 Hurricane Matthew caused widespread flooding in downtown St. Augustine