Clearwater to Newport

[Wilm]

I am planning a cruise from Clearwater Fl to Newport RI over a 2 week period (end of May thru early June). I plan to pass through the Keys at Marathon, stop in Charleston, SC then on to RI. I intend to stay outside and not use the ICW. Any advice would be greatly appreciated specifically relating to the Gulf Stream, Marathon key (I draw 5.5''), weather, Charleston harbor (access, marinas, anchorages) and Cape Hatteras (wisdom of going offshore vs the ditch)?

[camaraderie]

Charleston Harbor''s best deal is the moorings in the Ashley River just off the Municipal marina. Fee includes dinghy/garbage/facilities use at marina but size limit for boats in 40 ft.
You can also Anchor in the same spot but current is strong so be careful.

Personally, I would duck into Beaufort and do the ICW to Norfolk to avoid the whole Hatteras area on such a trip but of course many do stay well offshore for the trip...just be careful to have good weather forcasts before you commit to this! Two weeks sounds like you are really pushing the timetable from Clearwater.
Good luck...GB