First of all what are your priorities? Sailing, snorkeling, diving, relaxing, eating out? The distination are very much reliant on what you like to do.
Our first trip we ran all over the place, needed a week to recouperate when we got home. Once we had decided what we were going for the trips are much easier and we come back relaxed. As a point, we spend at least the last two days on the south side of St. John, no one ever goes there from the BVI's everyone stays on the north side, yet have found some of the best snorkeling there. My wife gets her one day of shopping in at Cruze bay and we normally sail to Buck Island for a snorkel before we return our boat to VIP at Compas point on ST. Thomas.
Are you going to prvision yourself or have the charter company provision. There are some great places to provision close to your harbor.
Anyway give me some ideas and I'll give you my thoughts. We have had our boat with VIP for five years and have yet to see 1/10th of what is in the area.