If you get a good weather window to make the trip, I would consider doing 2 nights at St Croix. Rent a car on the 2nd day and take a clockwise tour of the island. Note that if winds get to 18+ kts it wil be lively and bouncy sailing with 7+ foot seas, though the roughest is usually the first hour until you pass the south drop and get into more organized seas. Also consider how many days of strong winds there have been before departure as it takes a few days for the seas to moderate even if the wind has dropped.
Instead of 2 nights at Leinster, you might consider a 2 hr sail to Magens Bay on the 25th. Spend the afternoon and the next morning there, then return to Lovango on the 26th in the afternoon.
Salt Pond or Lameshur on the 20th is good to get your crew adjusted before jumping off for STX. Next day leave at dawn and you should get to Buck Island by 11 am. (Does your boat have the anchoring permit?) Spend the day, then leave for the marina or a Christiansted anchorage by 4 pm. Spend next day touring. On the return to STJ, depending on wind angle and drift you may find it difficult to make Ram Head in one tack so will likely be more comfortable to try to make Lameshur or even Christmas Cove, and then decide if you want to continue to north shore anchorages that day.
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