Howard, With plans to keep the conversation here instead of with
email, so that all on the forum can share ideas; I'd still ask about your draft and
mast clearance as these data will determine many of your choices. Also, will you be expecting overnights offshore or short day hops? What about your expectations regarding motoring and sailing? Are you planning to accept motoring for some inland passages or are you more inclined to sail only? If you are planning to do significant motoring, what is your cruising speed under
power? Also what are your time constraints for reaching the Keys? We don't often
cruise with deadlines and sometimes take as long as two months for this
route with many stops. Our first
ports out of Boston are usually Provencetown, Plymouth, Onset and
Newport. We find that Plymouth and
Newport have moorings available at a cost with little space for
anchoring, while Provencetown and Onset give us
safe anchorages and
dinghy access without costs. This brings up another question. Do you plan to make choices about your route that would allow for the least expense?
As I see Capttman's post above, those other resources are great!