Hmm...
Don't these threads get fun? I'd say forget about the pistol and get yourself a spooky gunship to fly close air support. There are even some based in North Florida, so that saves some on the gas... 20mm Gatling guns and a 105mm howitzer make even your polar bears and grizzlies want to think twice about stealing your trail mix...
Hey, I'm just having fun; not trying to put you down. I moved to Georgia from Florida (Bradenton) six months ago and I spent quite a bit of time in the woods and on the water while I was there. I ran into plenty of four legged and two legged critters in the woods and can't say I was ever worried about the four legged kind. Mostly the two legged variety was satisfied with a wave or an exchange of pleasantries and the four legged ones, well, they didn't stick around long enough to get acquainted.
I don't normally carry a gun with me in the woods unless I'm hunting but just for fun here are my thoughts as a former Florida resident. (I'm assuming from your post you are asking about Florida specifically)
You can't open carry in Florida unless on private land, so it's not like you can walk through the woods "man on point" style. If a bear gives you time to take off a pack and get a pistol out you've got time to go the other way. Sure, you can conceal carry as long as you aren't on National Forest land. Do you really want to hike in clothes to conceal a .44 mag or some such gun in 95 degrees and 98% humidity? Have at it but not me.
A couple of people a year get shark bit swimming, diving, etc. in Florida. Does that mean I drag my 48 special AB Biller speargun with me every time get past my knees in the water? No. (By the way, it's a lot of fun, try spearfishing sometime. Sort of like shooting a rifle underwater. At fish.)
Having been a Florida resident for 7 years, I can honestly say I would worry more about a trip to the quickie mart than a hike in the woods. I've run into gators, far too many snakes to mention, sharks, moray eels, (not in the woods) and some very curious barracuda (not the car), but none have hassled me for money or broken into my jeep. (Well, the neighbors cat did pee in it one time..)
Anyway, to keep this on topic Super-Dave, I can choose between a 9mm, .22LR, and a .44 caliber blackpowder as pistols I actually own. I'd go for the 9mm, because, well, if anything can soak up 15 9mm rounds and keep going, I guess it deserves to eat me. I'd like to think I would be tasty.
Super-Dave, I'm just bustin' your stones, but as a former Florida resident, enjoy that beautiful state but don't worry about the bears. If one attacks suddenly, unless you're walking around all combat patrol style, you're not going to have much of a chance anyway. But do watch yourself on the way to/from the woods. Lots of crazies down there.