Definitely a sensible idea to charter before you buy. However, just be aware that the
Virgin Islands (where I've lived and sailed for the last 18 years) is a bit like Disney World. The charter company will give you a clean, working boat, a comprehensive hand-over on its systems etc, and a good chart briefing on where to go, what to see. They'll even give you a friendly
skipper for a day or so to hold your hand if you want. If anything goes wrong, they will come out to you in a chase boat and fix it. (and, yes, things can and most certainly do go wrong!).
So, after a week of dead easy line-of-sight
navigation, a plethora of moorings balls so you dont have to practise
anchoring, benign winds and seas (normally!) in the protected waters, always within sight of land and
vhf distance to call for help, VISAR to
rescue you if it all goes bad; you will most certainly fall deeper in love with the
concept of cruising. Just imagine an afternoon on White Bay Jost Van Dyke, imbibing freely of Painkillers at the Soggy Dollar, leisurly motoring just round the corner to Great Harbour where you intend to spend the night partying at Foxy's....Oh, yes - This is the Life!! (Except of course that you actually
do have to
anchor in Great Harbour and the holding aint brilliant).
This, I suggest, is not "real cruising"!!! (Though its a lot of fun and has persuaded many a wife to join in a husband's dream) Tony