I understand wanting to stay in a nice place to continue the vacation vibe, I probably spend more time stressing about where I stay than anyone else I know.

How about spending the last night at the Sugar Mill on Tortola? It’s a lovely place with a wonderful restaurant and definitely has a vacation vibe. Then, in the morning, take a taxi to EIS. Hop on a Cape Air flight to STT. Looks like they are 288 per person. Super easy clearing in to customs there (last time it took us all of 10 minutes), and you’re right on the airport grounds.