I'm game to give it a go. I don't have a boat of my own (yet) and SWIMBO is not really all that keen to charter, especially if there are long flights involved, so I tend to go sailing with other people.
1) wisdom to choose airy saloon or cockpit instead of cabins
2) avoidance of small children/idiots for first three days by which time the "fancy a punch?" joke has run its course
3) ripping towards That Last Mooring Over There whilst other crew boards the dinghy, fires it up, lets go and nips ahead of all the competition. Yeehah!
Ahem. Anyway, twill be a bit sweaty if you fully crew up a sailboat in the bvi's i wd say. But there again, cheap. Take mosquito nets and (according to zefender) antihystamine wassername tablets for a week beforehand.
Skipperwise, there is not much need. Let's go over there. Oh alright then. But what about over there? Right then, we'll go there afterwards. A bvi boat should be big, easy and friendly enough for more than one skipper.
For decent sailing, best take the most ridiculous and least efficient criss-crossing routes everywhere. Obviously, it depends if you have become embroiled in some ad-hoc sailing race with some other boat who doesn't know they're in a sailing race (but probably, i bet they do).
bvi-wise, we go over christmas. We eat out in the evenings but I admit swmbo does all the "cooking". For example, she runs up ansd down the companionway stairs at about noon on christmas day trying to make an event of Lunch. "so, you are all saying that you just want a cheese and pickle sandwich, yes?" and "Look, are you sure you will all have a nice christmas lunch if i just make a cheese and pickle sandwich?" and so on.
This doesn't seem a daft idea at all. I think it wd probly be best to have couples sharing in a cabin, or singles a bunk each in the fwd bit. But generally not a prob as there is a saloon for snoozing in, and nicest snooze of all on deck (with the cushions, check that they havem..)
Note that mankiness-wise, boats in the carib are of two types : those with aircon, and those without. This is the only main difference that makes a real difference. They all have fridge and blah blah, and you can 19000 showers a day of the back so no problem. I have yet to rent one with aircon, but on a hot day swmbo and i had a good look round (inside) one with aircon blasting away, yes yes v intersting and only 6 grand a week what fab value, hee hee.
Next stage is to get His Kimliness to set up a specualtive forum about it, praps?
Rightyho, well all the more reason for a new forum. Why, i understand that some dumb clucks have even been able to organise entire shindigs in London on the basis of saying " i know, let's have a party in London".