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Hi Brett, I'm new to sailing too and shared the same dream. Also in Tampa. My family and I took an ASA course from SmarterSail, they are based in St Pete at the Magneson Resort next to the Skyway bridge.
Our plans were to buy a 25-30 footer but an acquaintance had a little Apollo 16 to get rid of and we took it on. Never thought I'd like the whole trailer thing (or small boat) but both are really great. The Apollo is making us more competent sailors and we can put the boat in wherever we want to sail for the day.

We have been invited to the above stated Thursday nights at Davis Island, have yet to make it but the people all sound nice.

One other source, is a Meet Up group I came across for sailors with and without boats. I've never hooked up with these folks but it sounds great --well, I need one more post before I'm allowed to add links but if you google tampa sailing meet up groups, it comes up first.
Good luck!
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