If you're looking for a Caribbean trip, check into whether her timeshares are available on Nevis or Guadeloupe. They're great, but more costly than a lot of the other places you could go down that way ... good place to use up a free stay! February or March are a great time for a winter getaway. For something unique, you could daytrip from Nevis or Antigua to Montserrat. It was nearly wiped clean by a volcano a while back. It's recovering by now, but still a rather unique place to visit, I would expect. It's about a twenty minute flight from Nevis.
LIAT flies into Nevis, Antigua, or Guadeloupe, you can connect in Puerto Rico.
Sorry Chickenmaven ... but I wouldn't waste a free timeshare on Jamaica where you could go on the cheap, and Aruba is rather arid. The water is nice, but I'd rather go someplace with more greenery!