First time poster here. I have the last week of February off work and am planning a trip south to do a variety of things, but mostly to do a couple days of guided fishing and perhaps some solo fishing as well. I am more interested in the in-shore species than the deep sea offshore stuff, mostly as in my few experiences the deep sea fishing usually means cranking in a medium sized fish on extra large size equipment then having the first mate or whoever hand bomb in the final 10 feet. I would rather be casting and reeling smaller spinning gear, or even fishing off the bottom for different species (snapper, grouper, etc).
I have read it is very windy that time of the year in the keys and don't know if it is worth coming down. Or is there a better area in Florida such as the gulf side that would be better? What about unguided fishing? Are there places I could go on my own? Not interested in fresh water, just salt water fish. (plenty of excellent freshwater fishing here)
Right now I am stuck between Florida and Puerto Rico. I have done some research and it seems there is some really good tarpon fishing to be had in P/R but getting there from Saskatchewan is a bit tougher than Florida so I would end of with less time, plus a bit more $$ to get there.
As of today I have used air miles to book my flight to Minneapolis, but am still pondering where to go from there.
I appreciate all responses and suggestions.

Wind is only a factor if you are there 2 or 3 days. After living in the Keys a year, I found that the weather will always let you fish after a few days. Even in windy conditions, backcountry is protected, so you can probably fish in the wind, but make sure you watch the weather, have a UHF radio and respect the power of the Atlantic and Gulf.

My preferred destination ... Islamorada. They call it "The Fishing Capital of the World" for a reason.