I’m happy to help. As mentioned above, November is a very tricky time for a sunshine holiday because so many of the better places have their rainiest season then. I agree about the DR. It’s an excellent place for big all-inclusive beach hotels, but outside the hotels there isn’t much of interest unless you are fluent in Spanish and hopefully know a local. One you might consider is San Juan, Puerto Rico combined with some stops elsewhere on the island. November is part of the rainy season there as well, but I don’t think it rains all day very often. And the city of San Juan is excellent for nightlife and things to do, so even if you get a couple rainy days you should be able to find some things to do. By then it’ll be over a year since the hurricane and San Juan has already been close to normal for a while now. There is still some damage, but it would be easy to avoid.
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.