You can't find a city in the U.S. older than Pensacola, Florida, founded by the Spanish in 1559. We finally nabbed it after it was under the thumb of the Spanish, the French, the Spanish, the British, and those darn Spaniards again. It went through a Confederate stage during the Civil War (when the North conquered Pensacola, they burned it pretty much to the ground, which is something they apparently enjoyed doing. See "Atlanta"). Pensacola also seems to get hit ALOT by hurricanes, starting the very same year Don Tristan de Luna y Arellano and 1400 of his closest buddies took control. The hurricane sank 5 of his 11 ships and killed hundreds--only about 50 stayed on but it was decided that northwest Florida was too dangerous to settle so the stragglers were relocated to Mexico and nobody resettled until 1694. For those who like to quibble, yes, St. Augustine, FL is usually acknowledged to be the first European settlement in the U.S. and while it was founded six years after Pensacola it had the good luck not to get wiped out by a hurricane and is actually the oldest continuously inhabited U.S. city. But as Wikipedia puts it, "The City of Pensacola, however, still occasionally refers to the area as 'America's First Settlement' in advertisements, signs and travel brochures." Just humor them, Wiki, ok?