St. Augustine, FLA
What a great base to tour Northern Florida/southern Georgia from for a weekend. America's oldest city is walkable, colorful, with a great waterfront, balanced with as many java huts as bars and as many dive hotels as swanky upscale ones, with as many activities for kids as for adults, and it's easily accessed from I-95. The vibe is Williamsburg with Charleston/Savannan esthetics but without the spoon-fed history and the re-enactors. I thoroughly enjoyed my overnight stay there last month on the moto and look forward to returning and scoping out new adventures.
So if you have any beta on St. Augustine, here's the place for it!