It would be best if we had some good cold front action bringing westerly winds for your time on the west coast. There are some east wind spots in Tampa, not too far from Ft. Myers (last time I checked, some bans are happening). Mainly though south to west to northerly winds are often best. Tampa has Ft. Desoto and locations that work in most wind directions. More about that at
http://fksa.org/forumdisplay.php?f=10
You can find out more about Ft. Myers and Naples at:
http://fksa.org/forumdisplay.php?f=24
As for the Keys, Whale Harbor and Anns Beach in Islamorada and Smathers Beach in Key West come to mind. There are sea taxi operations to Florida Bay for westerly winds if the fronts cycle those conditions through during your visit. More at:
http://fksa.org/forumdisplay.php?f=7
Have a good trip!
Rick