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.
My recommendations depend on your starting location so for now I’ll just assume you are starting somewhere in the USA. If you are looking for a really nice beach AND really good night life your best choices are the Cancun area, Puerto Vallarta, and San Juan, Puerto Rico. If you are in the eastern US or Canada it’s probably faster and cheaper to go to Cancun and if you are in the west Puerto Vallarta is better. San Juan will be more expensive because there just aren’t many cheap hotels in the good parts of the city. For the Cancun area I would recommend Playa del Carmen (about an hour south of Cancun Airport) because there are fairly cheap hotels near the town center, which is packed with bars and restaurants. In Cancun itself the best nightlife is in the heart of the hotel zone, and all of the hotels there are pretty expensive. Let me know if you have any other questions. -Roger
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.
While the Caribbean destination tends to overflow with families during the holidays in December, go a month earlier and you’ll be treated to sunny days sans screaming kids, plus less expensive airfare. “November is my one my favorite months. The hustle and bustle of high season hasn't kicked in, average temperatures are in the 80’s, and the water temperature is lovely,” says Michael King-Hew, the proprietor of Kamalame Cay, a private island resort in the Bahamas. King-Hew specifically suggests for the resort's annual wellness retreat. “It’s the perfect way to get rested and in shape before the start of the hectic holiday season.”
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.
Yes, these lists are reviewed and updated at least once a year. I’ve been adding new cities each year and even removing a few that have become too expensive to be on a “cheap” list. Personally, I’m an obsessive travel planner (which is why I do this for a living) and I like planning at least a few months in advance. You usually get the cheapest flights around 3 months out, although it can range from 2 to 5 months for longer flights. In other words, now is a great time to plan a November trip.
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.
Lace up your boots for an end-of-year adventure at the wild ends of the Earth. December is the ideal time to explore Patagonia’s mind-blowingly beautiful Torres del Paine National Park. Embark on an epic trek along the eight-day circuit, or take the four-day ‘W’ trek for Instagram-worthy views of Los Cuernos (the ‘horns’), the region’s iconic jagged granite peaks. Similarly breathtaking experiences can be had diving the coral reefs around Thailand’s Similan Islands. Beneath the sparkling surface of the ocean you’ll find sharks, barracuda, rays and green and hawksbill turtles – it’s Finding Nemo brought to life.
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.
Thank you very much Roger. I truly value your insight and am taking into consideration everything you’ve noted above. I’m going to check out the link you posted as well. That just reassured me that Bali would be great during that period. I’m thinking principally of staying in Ubud, Sanur or Seminyak for the type of trip I have in mind which is equal parts warm weather, walking/discovering, culture and some beach life. I’d love to visit Thailand but it’s just not the right time. At this point, I’m more intrigued by all of the many, still remote islands of Philippines than the chaotic lifestyle in Thailand. Perhaps, that’s just me still reeling from my trip to India a few months ago.
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. 
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