- August 28 – Sighted land of Florida on St. Augustine’s feast day
- September 7 – Captains Morales and Patiño disembark with 30 men to dig an entrenchment to protect people and supplies while the site of the fort is more carefully chosen
- September 8 – Menéndez formally claims Florida, unloads two of his ships
- September 20 – Menéndez and 500 soldiers march on Ft. Caroline, capture the fort and rename it San Mateo
- September 27(?) – Menéndez returns in triumph to St. Augustine, with 200 men
- September 29 – Massacre of French at Matanzas
- October 11 – Second massacre at Matanzas
- October 30 – Fort San Mateo burns, including its stores of supplies
- November 1 – Menéndez takes 250 men to Cape Canaveral, captures French survivors there. Before leaving, Menéndez marks out the fort at St. Augustine, and establishes a work schedule for the soldiers to build it. Their tools were iron poles, mattocks and hatchets.
- Early November – Menéndez establishes a garrison near the Indian River in the Ais territory, leaves 250 men there under Captain Medrano. Menéndez goes on to Cuba.
- December 13 – Spanish troops leave Indian River, go south to Santa Lucia
- End of December – Diego de Maya arrives in St. Augustine with relief supplies from Cuba. He goes on to the San Mateo fort, but loses the ship and half the supplies before he can land.
- March 8 – Mutiny at St. Augustine
- March 21 – Menéndez arrives in St. Augustine, quells mutiny. Brings survivors of St. Lucia
- Early April – Menéndez leaves to explore Guale region
- April 1 – St. Augustine fort “half burned”. All supplies lost.
- April 13 – Fort San Salvador established at Santa Elena
- May 18 – Menéndez returns to St. Augustine from Guale, decides to relocate the settlement and fort
- May – New fort laid out and built on Anastasia Island in 10 days
- Early June – Mutiny at Santa Elena
- June 21 – A relief fleet of 17 ships from Spain arrives in the newly-located town and fort of San Agustín on Anastasia Island. They brought supplies with which to build a substantial fort. This third construction of June 1566 incorporated part of the second, April 1566 fort.
- May-June – The settlement is abandoned, and rebuilt across the bay of St. Augustine on Anastasia Island
- July, 1567 – Menéndez orders that blockhouses be established in hostile Indian territories. The first was to be at “Polican”(near the entrance to the Matanzas River). In the interval of construction, Capt. Hernando Munoz and his lieutenant with fifty of their men were to stand guard. A second blockhouse was to be erected alongside the first, and here soldiers were to be stationed constantly so as to watch the movements of any ships at sea. The blockhouses were to be built on high ground for maximum effect and were to remain in communication with St. Augustine. The entire island was to be kept free of Indians, since the natives, subjects of Saturiba, are enemies of the Spaniards…“Still another blockhouse, similar to the one at Polican, was to be erected in Soloy, in the district of cacique Soloy, by Francisco Munoz with about the same number of men as was assigned to Polican. Construction of this last-mentioned post was to be undertaken by the end of July, 1567. Other outposts were planned on a height overlooking the residence of cacique Alimacani (across the St. Johns River from the town and blockhouse of Saturiba) , and at “old St. Augustine”. All of these blockhouses were to be built in the designated places to overawe the unfriendly Indians who had never desired alliance with the Christians.” (Barrientos, in Quinn 1979(II). P, 532)
- Indians of war had gathered at Casa Fuerte of “San Agustin del Viejo” (Lyon report 1997b: 104)