Matt - I asked my longtime good friend your question because I knew he would have an answer! His suggestion below:
QUOTE:
"I have sailed to St. Croix several times. I always used either Moorings or Sunsail since they were to only charter company that allowed sailing to St. Croix.
Almost all my trips were ASA teaching trips. I liked sailing from the BVIS to St. John’s to clear customs making it easier when you arrive at St. Croix.
In St. Croix, customs is at the airport.
Option 1 - clear out of BVIs and spend the night at the Bite. Then head out early for St. Croix to clear customs after arriving.
Option 2 - clear out of the BVIs and sail to St. John’s. I think you can now clear customs online. I always stayed at Little Lamshire Bay on south St. John’s. This is a beautiful place and you will be all alone.
Then sail to St. Croix. This is a better angle of sail. You will have to anchor in Gallows Bay.
We always took a day ashore touring St. Croix. It is a really great place. "