When contemplating a long tour, it's wise to do research and ask questions, which I do, much like you're doing. It can make a huge difference in your enjoyment of the trip. As has been cautioned, the prevailing winds blow south (stronger the further south you go). The eastern seaboard is the opposite. Along the south, it's a crap shoot, especially during storm season. Veteran cycle-tourers I've asked say if you're only going one way, go with the prevailing winds, otherwise, go to the farthest point and cycle back....the closer to home, the less likely you'll be inclined to give up, and if you have problems, the cheaper and easier it is to get home.