This is a tricky one. Pretty much every destination in the Tropics has its peak rates of the year during the weeks you have in mind. That said, there are still some fairly cheap destinations in the Caribbean, even at peak rates. However, since you live in South Florida and understandably don’t want to go someplace even hotter during the only semi cool time of the year, it sounds like you are ruling out most of the Tropics.
As you suspected, this is a tricky one. Most of the places that would work for you are having a very rainy month in November, so it’s not a good time. Thailand would actually be a good choice if you can deal with the travel time. The rainy season there ends in October and yet the crowds don’t start appearing until December, so you get low hotel prices with nearly perfect weather. As mentioned, all of the good options in Central or South America have a wet season in November. Argentina could be a good option, as November is late spring there, and it has everything you are looking for. The flights to get there are also fairly long though.
The same resort that charges US$300 per night in January will usually go for US$200 per night in November, especially earlier in the month. And this goes for all-inclusive resorts as well, which start at US$116 per night for two people in the low season when we last looked. If your main goal is relaxation in a perfect climate, Punta Cana is probably the best value in the entire hemisphere. And if you are wondering where to go in November for a beach all-inclusive then this is your best choice.
From England I would say your cheapest and best late December destination with warm weather and reasonable prices is going to be Phuket. There are some other Thai islands that might be a bit cheaper, but they would be more complicated to reach, and they’d have fewer activities for the boys. Here are some Phuket resorts good for families. You can see that the price range is wide from cheapest to most expensive. In late December it’s peak season so you’ll pay at or near the top of those ranges.
For anyone considering a multi-destination South American trip in November, Santiago should definitely be looked at. The daytime temperatures should be pleasant and warm, and it's bone-dry all summer, so it's a great combination. Hotels in Santiago don't have their peak price season until New Year's, so in November you'll easily be able to find a very good rate at one of the nicer places.
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.
The Maldives could be great if you can afford it. December is the most expensive month there, at least the second half of December. There are about 100 private-island resorts there, and most of them have water villas that start at around US$400 per night and go WAY up from there. But island rooms are cheaper. I wouldn’t recommend going to Male or any of the other populated islands that have several smaller hotels. It’s just not the same experience that you get from the private-island resorts. I can help much more with this if you decide to go to the Maldives.
Thank you. I think Kauai, Cancun, and Costa Rica could all be good choices for you. You’ll be looking at the last month (more or less) of the rainy season in each of them, but in the Tropics that usually means at most a few quick thunderstorms per week that typically last only 30 minutes or so. Kauai would be the most expensive of the three, although the most beautiful as well, and the easiest to visit since Spanish isn’t necessary at all.
Early in your message you say the last week of November, and then later you mention “late December,” so I’m not sure which it is. But if it’s late November, I think Italy could be a great option, as the weather there is still quite nice, at least in the south. You could go to Venice for a day or two and then Florence and Rome, and then maybe spend 5 or so days in Sorrento. I spent 5 days in Sorrento in mid November two years ago and the weather was very nice, even if it wasn’t warm enough to sit on the beach.
Actually, most of the popular European cities have fairly mild winters, in that they don’t spend much time below freezing and snowstorms are rare as well. It’s hard to make suggestions without knowing about your tastes, but I will tell you that the most popular European cities are London, Paris, and Rome, and none of them get snowed in often. If you are going to Italy, you should also go to Florence and maybe Venice as well.
By early December the rainy season is pretty much over in Cartagena, and it cools down just a bit more as well, so the weather really doesn't get any better than this. As with most others on this list, right around Christmas you'll find that hotels get more expensive and are more crowded, so if you can go earlier in the month you'll be paying less and dealing with fewer crowds.
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.