Our first stop on our Florida road trip, Saint Augustine is the “longest continuously inhabited European-established settlement” in the US. I’ll be honest, I’m not sure exactly what that means. There are clearly some technicalities behind its official designation, but it was established in 1565 by Spanish explorers and is basically the nation’s oldest city. The city’s Spanish roots are seen throughout, from the Castillo de San Marcos to the gorgeous campus of Flagler College. Sitting just across the Georgia border, Saint Augustine is packed with history, architecture, and incredible views, making it a great introduction to the state of Florida.