For a beginner at chartering the BVI's is the best place. All sailing is eyeball, short trips, lots of good anchorages. It does get a bit crowded but there's still lots of room especially if you anchor rather than pick up moorings. Another good point is that support is close at hand. Nearly all the companies have good chase boats and all boats are cell phone equipped so you can just call them if you need help. The only down side at that time of the year is that the winds might be a bit stronger (the Christmas winds) but then again, these winds sometimes continue to February. Bahamas is not a good spot for chartering in December especially the Abacos. If you are unlucky enough it might be one cold front after the other and if you've only got two weeks it's a real bummer. Sailing is easy but weather is iffy. At least in the Virgins it's 84 degrees and sunny with the odd shower. For the Caribbean I would think that the Virgins are your best bet. Lots of different companies too so you can shop around for the best deal.
Toronto in summer, Bahamas in winter.
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