Yes And Yes
The west coast of Fl. and the entire gulf coast for that matter is a really great cruising area. Plenty of destinations north or south of the Tampa that are easy and nice sails. Plenty of marinas and nice anchorages. And there are plenty of sailors on this board from that area. If your not at all familiar with the area, you will find that in the south, people are generally more easy going and more laid back and friendly. Last but not least, sailing down here is pretty much a 12 month a year thing. You don't have to pull and winterize your boat, instead you go sailing.