Sailing on the Gulf Coast, you'll have a lot of time on the water. The best area to go out of is JP or Clearwater, either one. S, SW winds are great! If you need a crew or new, give a hollar, I know the area. Welcome if your heading this way. Shoot me an email. I am also on skype: WWCorrigan, give a shout or email.
PS. Stay away from Tarpon and above, it get too shallow quickly in areas. Depending on keel size it's a mine field. Even though it's soft sand, not rocks like the east coast, still, you do not want to be spending your days "stuck". If your doing the ICW crawl, going towards the Skyway, you'll have some concerning areas as in shallow, stay within markers. Some of the bridges are timed, 15min. and 1/2 hour wait, see chart for details or call bridge tender(s) for details. They are pretty good.