Well it's not much of a challenge if that's ALL you want to see - just a lot of sailing. Or rather motorsailing, since you want a cat and you have a specific itinerary you want to fill.

Day 1 - STT to WE, check in, and Norman/Willy T for the night.

Day 2 - motorsail to the Baths, then to North Sound and Saba

Day 3 - Hang out in North Sound for a day of relaxing

Day 4 - Long but fast downwind sail to JVD

Day 5 - Back to base in STT

I'd really suggest that you contact a broker for this one. (Maybe someone who represents both crewed and bareboats, like Ed Hamilton)It could be a challenge finding a boat who is willing to do only a four night charter in December. Of course, the closer to Christmas, the less likely your chances.

You might be better off ferrying to Tortola, or St John and meeting you're crewed boat there.

Your broker will find a way...

Have fun!