Take it from someone who has learned the hard way ***Enlist the services of a professional weather router*** I am sure there are a number of choices out there, but I use Chris Parker (
http://www.mwxc.com ). For less than a 100 bucks they will make you a custom
forecast (Chris will anyway) telling you when to leave, what your weather window looks like, what the
wind will be doing, what the seas will be doing, what the
Gulf Stream will be doing, and recommend a course for you. For me, it is the best
money I ever spent on
boating. If weather allows, along with Sparx, I would also recommend a stop in St. Augustine. It is a very nice place to go ashore and get some rest. Shanachie already posted to stay near shore to avoid the opposing current of the
Gulf Stream. We never get more than 10-15 miles offshore when we are Southbound and there are a couple of places in
Florida, such as West Palm Beach and maybe the
Miami area where the Gulf Stream can run as close to the shoreline as 1.5 miles. Enjoy your
passage. Maybe we will see you here in Key West.