Veracruz, Mexico - permanently settled in 1519 by the Spanish St. Augustine, Florida, USA - settled in 1565 by the Spanish St. John's and Harbour Grace, Newfoundland, Canada - settled in 1583 by the British Roanoke Island, North Carolina - settled in 1585 by the British, but settlement was unsuccessful. Ladoussac, Quebec, Canada - settled in 1599-1600 by the French Port Royal, Nova Scotia, Canada - settled in 1605 by the French Jamestown, Virginia, USA - settled in 1607 by the British Santa Fe, New Mexico, USA - settled in 1607 by the Spanish