If you can find a charter company that will allow a 1 way trip it is an enjoyable time during a 9 day sail - a day or 2 exploring Antigua then about a 35 NM sail West to Nevis and clear in at Charlestown where there are nice moorings for a day or 2 - an easy sail over to St Kitts for another day or 2 - about 20NM to Statia for an interesting overnight and a nice 30 NM sail North to St Barths for at least a 2 day stop then a daysail over to St Marteen - some good open water sailing but almost always line of sight but with some careful planning for departure and arrival times no difficult passages - barring bad weather of course. A good cruising guide is a necessity and with a lot of new harbors to navigate a lot of attention to charts is paramount. Clearing in and out of so many countries along the way on such a short trip will really take more time than you realize though. It is an ambitious itinerary with a lot more time underway than most people would care for on a vacation IMHO. People looking to really do some sailing would love it however. Bareboat restrictions on night sailing will mean some dawn departures for sure to allow for good afternoon light entries on the longer passages.
I have sailed those waters a lot in the last 40 years and early Dec. can get breezy and I would want to take more time to cover that amount of distance and enjoy more time stopped along the way than a 9 day trip allows. Everyone aboard should be sailors and the Captain should be an experienced sailor! - For a vacation ---- doing this trip on a crewed charter boat would be a much better experience for everyone involved and much easier to book with a Charter Broker.