1. St. Pete Beach
Pros: Laid-back people, packed beaches, excellent beach bars
Cons: Your life flashes before your eyes every time you have to cross Skyway Bridge to get there
St. Pete Beach is a magical place, both because it makes you feel like you’re not in Florida and because the people/vibes are ridiculously cool. I was there during a Category 3 hurricane once, and aside from the tornadoes, you would have never known you were in a Category 3 hurricane. Everyone was busy drinking rum runners at a beach bar, totally unaware of the fact that said bar was flooded up to their ankles. Also in St. Pete -- not during a Category 3 hurricane -- I took “froot loops” shots with a guy from Hells Angels who later gave me a skull necklace (he was quite friendly!). Anyway, St. Pete Beach is No. 1 on my list because it can be anything you want it to be: quiet, a non-stop bacchanal, a foodie getaway, a family reunion spot, a romantic escape, a bachelor/bachelorette party destination, or just a weekend trip to get some R&R. And while you’re there, don’t forget to stop by the authentic Italian sandwich shop Mazzaro's, the Chihuly glass art exhibit, or the Dali museum. Hey, who knows, you might even meet a friendly Hell’s Angel who’ll buy you "froot loop" shots and give you a skull necklace.