1. St. Augustine - can't be as Republican as Sarasota
And it has the history thing going. Plus, there is a strong artist community there. Around St. Augustine there are a lot of really cool historical sites, much more than just the fort.
Sarasota is where what her face, the Secretary of State that allowed the voter purge while she was the state chairman of Bush's campaign in 2000 - Katherine Harris. AND they elected her to Congress after that!