The English failed in their first efforts to settle the New World, at Roanoke Island in 1585 and 1587. Jamestown, settled finally in 1607, is famous as the oldest English settlement in North America. However, the English were not the first Europeans to try to colonize the Chesapeake Bay.
One of their first attempts at settlement on the east coast of North America was in 1526, when Lucas Vazquez de Ayllón founded the colony of San Miguel de Gualdape. It could have been in South Carolina or Georgia around the 33 degree of latitude1, but some2 have confused this 1526 settlement with the 1570 attempt by the Spanish to start a settlement in the Chesapeake Bay.
In 1561, Pedro de Menendez de Aviles sailed into the Bahia de Santa Maria. He convinced (or seized) the son of a chief to travel to Spain.3 Paquiquino, the 17-year old son of the werowance at "Ajacan," and a companion from the Chiskiak town on the York River, were the the first Virginians to visit the Old World. They were exhibited to the Spanish royal family and society "at court" in Spain. This allowed Menendez to impress people (including potential financial backers and political supporters) at home, and to expose the Native Americans to the grandeur of European culture. It also showed other Europeans that Spain continued its leadership position in exploring and discovering riches in the New World.
Paquiquino was taught the Spanish language and the Catholic religion (by Dominican friars initially, then later by Jesuits in Mexico). Paquiquino was also quizzed at length about the mineral resources in his area and any rivers that could have offered a path to the Pacific.
The "freshman year of college" in Spain lasted from September, 1561 to May, 1562. Menendez then took Paquiquino to Mexico for more training. In 1566, Menendez arranged for Paquiquino, by now known by the name of "Don Luis," to go back to the Bahia de Santa Maria/Chesapeake Bay. Apparently the Spanish ship could not find the entrance to the bay, however, so Paquiquino/Don Luis was carried to Spain again. In 1570, he was finally brought back to Virginia in a party of Jesuit missionaries led by Father Juan Baptista de Seguera. In September, 1570, they sailed up Powhatan's River (it would not be named after King James for 35 more years...) to a tributary later named College Creek, about 5 miles downstream from what later would be called Jamestown. Paququino/Don Luis led the group across the peninsula to what the English would later name the York River, where they discovered his younger brother was a werowance of an Algonquian-speaking town.
The small band of missionaries expected to rely upon Paquiquino/Don Luis to negotiate with the Virginia natives to obtain food; no one had learned Algonquian, the local language.
Paquiquino/Don Luis had been exposed to Spanish culture in Mexico, Spain, and Havana before being returned home to the Bahia de Santa Maria with eight priests and a novice who was training to join the Jesuits. But how much was Ajacan "home" to him? Think an Algonquian who had spent much of his adolescence and all of his adult life in Spanish culture had a clear understanding of where was his home?
Despite all those years in Spain and Mexico, Paquiquino had sought to return to Ajacan. He convinced the Spanish to carry him back to the Bahia de Santa Maria twice. (Paquiquino may have called it the Chesapeake or "great shellfish bay," if he retained his pre-capture terminology. Queen Elizabeth had become ruler of England in 1558, but no one called anything in the New World "Virginia" yet.)
The Spanish gambled that "Don Luis" would follow the Spanish way of life after being reintroduced to his village of Ajacan. Instead, Paquiquino quickly demonstrated that his personal choice was to return to his tribal lifestyle. He moved to another town, and took several wives in accordance with his status in Virginia society and in clear contrast to his Catholic teachings. Obviously 9 years in Spain and Mexico had not erased 17 years of Virginia acculturation.
Paquiquino and his tribe was unwilling to support the Spanish missionaries - it was a drought year, and the Native Americans refused to provide food or supplies for free to the missionaries. By December, the Spanish had traded away their tools for food. In February, 1571, after Father Seguera appealed to "Don Luis" for aid, Paquiquino eliminated the Spanish settlement. He followed Father Seguera back from the appeal and (with others from the town) killed him and all the other missionaries except for a young boy, Alonso de los Olmos.
This was not the end to the Spanish colonization effort, however. A passing Spanish ship discovered the situation in 1571. In 1572 another ship returned to "rescue" the boy and punish Paquiquino and his people. In the end, nearly 40 natives were killed, including 7 hung from the ship's rigging in full view of the people on the shoreline. The boy was returned to Spain, and future attempts at settlement in Mexico were designed to be self-sufficient in food and translators. The Spanish did not attempt to settle Virginia again. Instead, they tracked English activities in North America through spies in England, especially after the Treaty of London in 1604 opened the way for English colonies in the New World.
As a result of the Spanish visits to the Chesapeake Bay, the Native Virginians gained a warped - or perhaps clear - understanding of European behavior. Perhaps the sight of seeing their captured men hung from the ship's masts in 1572 left a lingering image that affected the greeting given the next visitors in sailing ships in 1607. One especially-intriguing possibility is that the Native Americans in Tidewater Virginia learned about European culture and empires from Paquiquino/Don Luis. The English who settled at Jamestown discovered an unusual confederation of the tribes under Powhatan. The political sophistication of the Powhatan Confederacy may reflect the unique understanding of another culture, provided by one Virginian who was trained by the Spanish in the European liffestyle.
In 1564, the king of Spain (Phillip II) decided to eliminate the remnants of the French colony at Charlesfort. Manrique de Rojas led the expedition that burned the remaining buildings, but shortly afterwards another French expedition built Fort Caroline near what is today Jacksonville, Florida. In 1565, Pedro Menéndez de Avilés started a settlement at St. Augustine to support the large force (1,000 men, 10 ships) that captured Fort Caroline. Menéndez made clear that the Spanish would allow no French settlement near Florida, by executing a large number of captives at Matanzas Inlet. He built his own fort, Fort San Mateo, on the ruins of Fort Caroline.
In 1566, he also started a settlement at Santa Elena and a fort called San Salvador. A year later, another fort (San Felipe) was constructed there on top of the old Charlsfort. In 1580, over 25 years before Jamestown was settled, there were 400 people living at Santa Elena. Spanish fortifications on the coastline north of Saint Augustine were abandoned in 1587, after Sir Francis Drake attacked and captured Saint Augustine in 1586 (before stopping at Roanoke Island and bringing the english settlers at that colony back to England). The Spanish rebuilt that fort, and concentrated their military resources in Florida to protect the sea traffic through the Caribbean.
NOTE: Saint Augustine, Florida, settled in 1565, rightly claims to be the oldest continuous European settlement in North America. In 1598, Spanish explorers settled in the Tewa town of Ohkay Owingeh, renaming it San Juan de los Caballeros. The Spanish established the first capital of New Mexico nine years before Jamestown. They moved along the Rio Grande to another town (Yunque), then finally settled at Sante Fe in 1610. In the winter of 1610-11, the English almost abandoned their colonial settlement in Virginia.
Other sources:
Lowery, Woodbury, The Spanish settlements within the present limits of the United States, 1513-1561, New York, G.P. Putnam's sons, 1911
Milanich, Jerald T., Laboring in the Fields of the Lord: Spanish Missions and Southeast Indians, Smithsonian Institution Press, Washington, 1999