I did my write up and posted the pictures of my trip to the Keys that started in Flamingo (the Everglades).
http://miami2montreal.wordpress.com/I learned quite a few things during that trip, much of it would help anyone wanting to do a similar trip. For instance, the way the keys are oriented makes it easy to go from East to West but it's less easy going the other way. In my case, it was easy sailing since I chose to go where the wind took me. The other thing, going toward Key Largo means spending good money on campgrounds since there is a lack of primitive sites going that way. Also, the Florida paddling guide is a great tool but some information is now outdated (Long Key national park does not have primitive campground anymore, instead they park you on platforms 2 miles west of the coodinates given by the guide).
I was doing it to prepare myself for my final departure from Miami, it's very soon now since I want to take full advantage of the south east winds.
BTW For those who can read French, there is an hilarious blog about my blog at
http://miamiamontreal.wordpress.com/