Intercoastal around Florida
Just got back from that area 2 weeks ago. No problems transiting the ICW proper. Nice anchorages headed south at the north end of Longboat Key, Sarasota, and free (18 Hour) dock at the Venice Yacht Club. Cabbage Key, Useppa, Captiva, ands Sanibel still have clean up going on and some limited facilities after the Eye of Charlie passed right over.
Can''t comment on the "Ditch". Hopefully someone will comment further. I recall reading that the max mast height is restricted to 45 - 50ft(?) due to fixed bridges. You could always step the mast and save quite a few miles of travel. But then you''d miss the MASSIVE swarms of mosquitoes at Little Shark River in the Everglades. STAY CLEAR!!!
Skipper Bob has an anchorage guide for the entire ICW from Tarpon Springs thru the Keys and up to I believe Virginia. Well worth the $16.(Not a paid advertisement).
Why are you headed to the Chesapeake now? Or is this planned for spring? Enjoy the best time of the year now in Florida. Plus no hurricanes!