Where to charter?
The third option is of course the Greek islands. Both previous destinations are excellent Tonga, Thialand, Tahitai, etc unbeleivable and some what easy sailing and I am sure you can get real good discounts after this years Sars scares... Caribbean perfect as its only in your back yard and offers many excellent destinations, all well organized and definatley beautiful... then for a little more adventure Greece, as a beginner I would recommend the Ionian side of the country, that is the western side of greece. Base your selves out of Levkas and sail around the gulf visiting places like Ithaca, Kefalonia, and Zakinthos, a week should be more than enough. Over here Sunsail run a very tight operation with good yachts and great hotels and resorts that offer the beginner the chance to do both sail a yacht and still have some down time in a comfortable hotel....
Moorings also offer the same service but a little more money..
Good luck with your choices let us know if we can offer any more ideas