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 in this working city: 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.
The people who live and work here do so because they're born into it and have become part of the fabric of this historic place, or, they've moved here because they're passionate about what they do and want to be a part of that history. For that reason, you'll find a stunning array of wonderful B&Bs, cozy cafes and lamp-lit pubs. While fine-dining might not be the first thing that comes to mind at Florida's mention, it is certainly synonymous with St Augustine, whose charming one-off cafes and numerous impressive restaurants are the real deal too.
Plan to stay at least two nights if you can: you certainly won't run out of things to see, taste, or learn.