I can't really comment on the STX portion but we have done the trip from STT to Culebra before. We had a NE wind and a nice sail to Culebra and cleared in with CBP Roam app. Spent time in Ensenada Honda which was okay. Anchored in Ensenda Sun Bay on Vieques after a nice sail from Culebra and visited the Bio Bay which is a cool experience. Sailed back to Culebrita which was our favorite stop in the SVI. We left Culebrita and headed North with an ENE wind and eventually tacked on a course to Sail Rock and one more tack into the lee of STT before motorsailing the rest due to needing to drop off a few guests at the airport. Seas only 2-4 ft until we were in the lee of STT. My point is, I did not feel that it was a horrible upwind beat like has been described at least for our conditions. We did eventually bring down the sails in the lee of STT which cut some of our wind and in order to get to the airport in time.

I think the weather forecast would maybe dictate my course. A NE wind and I likely would go counter clockwise. A SE wind (probably more likely that time of year) would make the Vieques to STX leg very difficult and would consider the clockwise route which also would make sense I think with East wind. I'd rather beat for 14 nm than 32 nm. Others can probably chime in with experience with the STX portion though but obviously the weather will rule the day and decision making.

I am not sure about clearing in at Vieques. I believe they have a designated site at Mosquito Pier and can still use your CBP Roam app. You could probably anchor on the South side and make the call but if you had to present would have to make the trip around to the north side. Hopefully someone has some experience there.

Sounds like fun regardless. Hope you can make the trip!