Maybe I'm being too easy on it, there is a lot of stuff going on in the middle of this flag, but the imagery of the Native American watching the steamship sail by is appealing, ignoring the fact that a scene like this probably never happened.
The easiest way to fix this flag would be to remove all the stuff in the middle:
This flag still resembles Alabama, but the large golden disk could easily be said to be the sun, Florida is the Sunshine State after all. It would be simple, easy to draw, and probably be fairly recognizable. However, suggesting this as the alternative makes me feel a little lazy, so let's see if we can do better.
Florida has a diverse flag history, going back to its colonization by the Spanish in the early 1500's. Here are three of the flags used over all or part of the state in the intervening years:
The flag of the short-lived Republic of West Florida (centered on the Gulf coasts of Mississippi and Alabama and part of Louisiana, there is some dispute over if it ever claimed any of today's Florida). This flag is interesting, it has a good historical connection, even if geographically it may be a little tenuous. However, the single star is a bit dull, particularly with the profusion of stars on other states' flags. Plus, it was used as the flag of secession across much of the South during the 1860's, so I'll just avoid that whole mess.
The flag Florida adopted in 1861, its first state flag. This one is also interesting, but mainly because it echos the 1st Confederate National flag in a way that seems to be unique; the flag is divided in half, with one side being blue and the other holding the three stripes. This one could serve as template for another Southern state in the future, but I think I have a better idea for Florida.
The flag Florida used from 1868 to 1900. This one is an approximation, as the seal has been changes in minor ways over the years, but it gives the same impression as the other would have. This flag is not the source of that better idea, I just wanted to let you know that Florida's flag used to be a lot worse.
The improvement idea comes from a flag that has been shown on this blog before and currently acts as one of the inspirations for Florida's currents design; the Cross of Burgundy:
It struck me as I studied this flag that it has twenty four little notches on it (or whatever you want to call those things) and Florida was the 27th state. It wouldn't be too hard to add three more and this would provide an unique way of denoting the state's position without using only stars again. Here is the end result:
I've changed the colors for two reasons, because I got sick of red and white, and because the green cross now resembles palm fronds, a type of tree synonymous with Florida. There are now 26 notches, one for each state at the time Florida joined, and one central orange star to represent Florida itself. This star can also symbolize the Sun and the orange color can point to one of the state's most famous products, citrus fruit. It has a distinct design, each element is (fairly) specific to Florida, and could easily be turned into a bumper sticker.