We did some extensive research on sailing the Keys. From Middle Keys south, it appears that you have very limited mooring/good hold anchoarages. There are some slips available, but they are expensive. Heading to the Dry Tortugas would entice me (we've been there many times via seaplane) but you have to have great weather windows. We passed and sailed the USVI last month and are here in the BVI on our new cat now (and it was worth every protocol measure to get here).