Re: Sailing from Charleston to Tampa
To get a good idea of what the gulf stream is doing, go to Passage Weather.com, click on the Sector Maps and select the area of the coast you're interested in and then click on the tab "Gulf Stream". You will be able to see the stream and the velocities at the moment and predictions for several days ahead. By and large, for 3-4 days at a time, passage weather has proven very reliable.
In general, heading south to about Cape Canaveral, you can stay "relatively" inshore and within northerly flows of 1 knt or less. Attempting to take advantage of counter currents will require you to hang too close to the coast which will sacrafice any advantage offered by such currents to greater distances and the flukie conditions of alternating sea/land breezes and put you into a more hazzardous area--the sea doesn't generally kill boats, its the hard stuff around the edges that does that. From Canaveral south, you can hug the coast and sail point-to-point, or go inside, to St. Lucie and then cross to the west coast on the St. Lucie canal, Lake Okeechobee, Caloosahatchie River route (provided you can stand the boredom). BTDT.
As long as you can sail in easterly through southerly to westerly winds, you should do okay. Any northerly components tho' will make for a miserable sail as that boat is an off-the-wind machine. It can be done, of course, and the boat is certainly up to it...if you are. Frankly, however, if you have a trailer, I don't see the point of beating up the boat, and yourself, for the sake of the exercise.
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."