St. Augustine, Florida

The oldest continuously occupied European settlement in the US, St Augustine was founded by the Spanish in 1565. Today, its 144-block National Historic Landmark District is a major tourist destination. For the most part, St Augustine exudes charm and maintains its integrity, although there’s no denying the presence of some tacky tourist traps: miniature theme parks, tour operators at almost every turn and horse-drawn carriages clip-clopping past townsfolk dressed in period costume.
What makes St Augustine so genuinely endearing is the accessibility of its rich history via countless top-notch museums and the authenticity of its centuries-old architecture, monuments and narrow cobbled lanes. Unlike Florida’s numerous historical theme parks, St Augustine is the real deal.

You’ll find a diverse array of wonderful B&Bs, cozy cafes and lamp-lit pubs, and while fine dining might not be the first thing that comes to mind at Florida’s mention, it is certainly synonymous with St Augustine.