LOts of questions...
A well-maintained, well-equipped C27 can make it to the Virgin Islands from SC with no problem. From SC, you go down the ICW to Florida (like Miami), then over to the Bimini in the Bahamas, then down the Bahama chain to the Turks & Caicos. Then over to Dominican Republic (probably the longest passage - I don't have charts in front of me), then East to Puerto Rico. From PR, you're within multiple day-sails distance to St Thomas. I'd guess there's not more than a few passages where you can't harbor-hop to stay in an anchorage overnight. If I were doing it on my C27, I'd be sure to have all the recommended rigging upgrades done (see the archives), and be sure I had at least one additional experienced, knowledgeable, trustworthy crew on at all times (preferably female, blonde and about 25-35 yrs). It's certainly do-able.... That trip is something I've dreamed about. Although all my ocean sailing is pretty much only West Coast-NorCal stuff. Your Carib venue is much more user-friendly than here, where heavy winds and fog are the norm. But it hasn't stopped me and my C27 from going wherever I wanted to and had the time.... Good luck!
