Sir Walter Raleigh established the first English Colony of Roanoke in 1585. Governor Ralph Lane was subsequently appointed to run the ill-equipped settlement.

Sir Francis Drake attacked St. Augustine in 1586. His forces destroyed the sixth wooden fort, San Juan de Pinillo, a predecessor of the Castillo de San Marcos.

Phillip II, King of Spain, sent his Armada's 130 vessel fleet against the British in 1588.

On May 14, 1607 the first settlers landed on Jamestown Island forming the Virginia Colony for England. This English colony was named for King James I who granted the land in 1606.

Antonio de Herrera Lopez y Mesa led Spanish soldiers and native captives to negotiate peace between the Apalachee’s, the Amacanos, the Chacatos, and the Apalachicola Tribes.

Charles II, King of England, created the Charter for Carolina in 1663.

Carolina Charter of 1665 enlarged the original grant for the Carolina Colony. The new boundary was defined as 29° north latitude, which extended into Spanish territory.

A pirate crew, led by Robert Searle (also known as John Davis) raided the city of St. Augustine in May 1668. Searle's men pillaged the town and murdered sixty residents, including children.

Queen Regent Mariana, spurred by news of the English attack on St. Augustine, made several requests for improvements to the city's defense in 1669.

Construction on the Castillo de San Marcos began in 1672. The Spanish used coquina to build the fort, making its walls virtually impenetrable and fire resistant.

The wooden watchtower on Anastasia Island was replaced with a coquina tower in 1683.

In the summer of 1686 the Spanish laid siege to the British city of Charles Town.

On November 7, 1693, Spanish King Charles II issued a Royal Cedula guaranteeing safe refuge to British fugitive slaves. Many slaves escaped the British plantations, fleeing to Spanish St.

Pensacola is re-established by the Spanish in 1696. Andres de Arriola arrived at his new post on November 21, 1698 and oversaw the construction of a fort, called San Carlos de Austria.

War of Spanish Succession, known as Queen Anne's War in America, allied Spain and France against Austria, Great Britain, and other European powers.

In 1704 work on the Cubo Line began in St. Augustine under Governor Jose de Zuniga y la Cerda.

In 1706 a Hornwork was built a half mile north of the Cubo Line, further blocking access to the city of St. Augustine from the north.

The Rosario Line was added to the city's defenses in 1718.

In 1721, Colonel John "Tuscarora Jack" Barnwell built Fort King George for the English.

Francisco Menendez, an escaped Carolina slave, came to St. Augustine in 1725 with the aid of the Yamassee Indians. However, once Menendez entered St.