Inspiring travel stories, tips, and guides from a couple exploring the world one destination at a time.
The “Nations Oldest City” is what St. Augustine is often referred to. It was founded in 1565 by Spanish explorers. It is the oldest continuously inhabited European established settlement in the mainland United States. San Juan, Puerto Rico is the oldest settlement, founded in 1521. Eventually, Spain ceded Florida to the United States in 1819. At the time, St. Augustine was the capital of the Florida Territory but it was moved to Tallahassee in 1824.
Last Updated: July 4, 2026
St. Augustine was the start of our Florida winter snowbird destination. It had been a few years since we last visited Florida, and after the previous winter’s cold, wet weather in California, we were looking forward to beaches, sunshine, and warmth. We were not disappointed — St. Augustine delivered on every front, from its gorgeous beaches and ancient masonry fort to its charming pedestrian streets and lively martini bars.
