There are quite a few Hobies in the Tampa bay area, if you see one at a launch site make sure you come up and talk to any of us. Every weekend you will see a few of us either launching at Ft Desoto boat ramps, or at City Island in Sarasota (Ken Thompson park right next to the Sarasota Sailing Squadron, I'm there most every weekend year round), both are very popular launch sites just to name a few.
The main Hobie dealers in the area are Tackle Shack in St Pete, and Economy Tackle in Sarasota. They both are very knowledgeable and can talk you thru what to look for and help get you get in touch with local clubs and groups like the Hobie Island club ( http://www.hobiecat.com/hobie-island-club/
) or the Watertribe ( http://watertribe.org/
), or Wet dog adventures just to name a few, all are very active and most are active on Meetup ( http://www.meetup.com/
I think the first place to start is to go into the Hobie dealer and just chat, make sure to ask about local clubs and groups, and outings. Most Hobie dealers have monthly events called demo days. Economy Tackles next demo day will be on the 24th ( http://www.floridakayak.com/index.php/calendar
). You can go to these and try out every type of kayak they have, and talk to experts about which would best fit your needs (that's exactly what we did, it was a blast, and we learned a lot), I'm sure Tackle Shack has the same if you are closer to them, I'm sure there are other dealers in the region, but these are the ones I know. We are extremely happy with our Hobie's, and the Hobie lifestyle especially in Florida where we can go out all year round. It is really something special, and fun.