PBzeer and some of the others have done similar trips and will be able to give you some excellent advice.
What do you have for an anchor currently... since you'll need a good one to do a trip like this. If you don't have an oversized anchor, I'd highly recommend you get a next generation anchor like a Rocna, Manson Supreme or Buegel. If not a next gen anchor, get a oversized Delta. You really want a good anchor that will reset if the current or winds shift. Get at least 30' of 5/16" chain on it and then the rest 9/16" or 5/8" nylon.
You'll also want to setup jacklines and get yourself a tether and harness. These are very important, since you're going to be single-handing the boat... you need to STAY ON THE BOAT.
If you don't have an autopilot, I'd highly recommend getting one... or at least setting up some sort of tiller self-steering, even if it is just a Tiller Tamer.
If you want to avoid motoring, you'll have to avoid the ICW, since the ICW is mostly narrow and requires most boats to motor for a majority of the time.
Good luck and keep us posted.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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