I'm making the same trip soon. Very interested in this discussion as I was going to start a thread on the same topic.
I've been studying the areas almost daily for several weeks now. It seems with even my 4' 8" draft
there are very few places to safely anchor
along the way. I'm looking forward to the experience but will be singlehanded in my first offshore cruise
with eight months owning the boat and about 100 hours on the water. I think I'm pushing the envelope for my experience level but a fellow's got to start somewhere.
I was thinking, Gulfport (near Tampa Bay) to Anclote Key (Tarpon Springs area), then to Cedar Key, then to St. George Bay (Carabelle).
Both Crystal River and Steinhatchie River look like a challenge to me.