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GC:
RC has given a very good summary of chartering in the BVI / USVI area.
As to your preferences:
The BVI will provide opportunities to do all the items mentioned. The time of year does matter as it affects cost, crowds, boat availability, etc along with the ability to truly appreciate the beauty & people.......true for all vacation areas but certainly for the BVI which hosts the largest charter "fleet" in the world.
There are shoulder periods that offer great sailing conditions, less crowds and often discounts...........so carefully planning can provide a great time.
Based on your experience & comfort, St. Martin & Anguilla could be an alternative & interesting option.
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