Ok, lots of advice, so I'll just put my favorites out there.
Vieux Fort, St. Lucia is one of the cheapest US/Caribbean tickets (big planes US direct) and the airport
is less than 2 miles from the anchorage. Good shopping
at local prices at a great supermarket walking distance to the boat.
Cays for a West Indian lobster dinner on the beach was our choice for Christmas dinner. Great snorkeling and you will see many (not just a few, I guarantee) wild turtles in the turtle area. Fresh bread and fruit brought to the boat each morning by enterprising locals.
Bequia has an incredible New Year's Eve celebration with fireworks about midnight. Rum
punch, dancing and great music
And real sailing, some of the best I've had in the Caribbean; we call them "romps" between the islands down there (smaller lees and better angles on the wind).