Re: Sailing from Charleston to Tampa
You can avoid the gulf stream easily until you get to West Palm Beach. You'll need to do overnights to get anywhere, otherwise you be spending 4 hrs just getting in/out the inlets.
Weather wise the best time of year would be spring/fall, you will have company if heading south in the fall. You will have to decide how much tolerance you have to being sleep deprived, if singlehanded, you'll have to do just short naps, get yourself a countdown timer that you slip to your collar to insure you wake up.
Most people will use the Hawk channel south of Miami to avoid the stream down to Key West. If you motor some, sail offshore when weather is good, you should be able to get to Tampa in about 4 weeks.
PS31#111 Cielo Azul