It would probably be a bit more expensive, but another idea that could be great would be to fly to San Juan, Puerto Rico, and rent an apartment for two weeks. It’s a wonderful place that is family friendly, and rental apartments can be good deals. It’s obviously peak season there as well so nothing will be cheap. But the weather will be fantastic and the beaches are great, even in and near the city. I hope this helps. Let me know if you have any other questions.
If you’re pretty simplistic when it comes to food, you can always bring nuts with you. They last long, they taste great, and they’re packed full of fats (if you choose correctly). Macadamia nuts and Brazil nuts are among the top high-fat nuts out there, and they’re well worth the extra cost if they save you from an accidental cheat right at the end of a great vacation.
For the record, the official Hurricane Season runs from June 1 to November 30, but hurricanes in November are extremely rare, so we have likely seen the last of them for this season. The devastated islands will need help rebuilding, and the remaining islands are hoping that visitors know they need the business as well, and that there is no risk of big storms starting in December and usually earlier. -Roger
It would be hard to beat Chiang Mai for its combination of great November weather and low prices. Even though it's officially the start of the high season for hotels, the beginning of the month is usually very slow anyway, so bargains are common. Hotels in Chiang Mai are among the best bargains in the entire world, so even if you do have to pay full price for a room it'll be cheaper than a dorm bed in most European cities.
Another option would be Cambodia and/or Vietnam. The town of Siem Reap, which is just next to the Angkor Wat Temples is the real highlight. Phnom Penh is worth a quick look, but not on a shorter trip. Vietnam itself is a wonderful and gorgeous country, and you can see a lot of the highlights in 10 days or so. It’s also very cheap, even around Christmas. You could fly into Hanoi and then go see Ha Long Bay, and then take a train down to Hoi An. After that you could go to Nha Trang for the best beach experience or the hilltown of Sapa. The city of Ho Chi Minh City is quite crowded and you might not like it for more than a day or two.
The rainy season usually ends early in November in Siem Reap, and the tail end of it is rarely fierce, so this is an ideal month to hang out in town and spend multiple days at Angkor Wat. November is actually the coolest month of the year, by just a bit, at least during the days, so most people will appreciate more moderate temperatures when climbing up and over all the temples.
Vietnam and Sri Lanka could both be excellent choices for what you have in mind. Both are best for people who already have experience in these sorts of places, which you do. Twelve days could be a perfect length of time for a classic tour of Vietnam, flying into Hanoi and spending a few days there and in Halong Bay (with a possible side trip up to Sapa), and then taking the train down to Denang for a quick transfer to Hoi An. Hoi An is really a wonderful place and 3 or 4 days there would be great. There are good beaches nearby as well. Then take the train down to Ho Chi Minh City for a few more days before flying home from there. You could also do a side trip to Nha Trang (wonderful beaches) or Dalat up in the mountains. Vietnam really is gorgeous and the food is wonderful (French influences remain) but it can be a bit complicated for new travelers because you’ll find that many people you meet are trying to hustle you a bit, particularly travel agents booking trips and tours. The hotels are generally honest and great value, and so are the restaurants. You’ll learn to ignore the annoying people quickly.
The high season hotel prices will start in November as well, but crowds are usually thin for most of the month so you should be able to get some nice bargains at some of the nicer places that allow online booking. When they see that they have lots of empty rooms as the month approaches, they'll discount to be on par with some of the 2-star places that aren't nearly as nice.
As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.
Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.
Don’t be too shy to ask the wait staff how the food is prepared. If you suspect something might be breaded ask. Ask if any of the dressings have sugar in them. In Italy it’s not common at all for savoury food to contain any sugar, even the sauces. Most are based on olive oil or cream. If you order a steak without any sauce don’t be afraid to ask for olive oil to use on it. You might get some strange looks if you ask for butter and they might not have any available. Try to go for roasted or grilled food rather than fried as even in Italy, the spiritual home of olive oil, the food is usually fried in vegetable oils. Also don’t be afraid to ask for substitutions. I don’t like bell peppers and they always come as part of grilled vegetable sides. I simply ask them to leave them out and I’ll get more of another type of vegetable instead.
Trekking in Nepal during peak season might not sound like the most sensible choice for penny-pinching backpackers. But you can still enjoy the ideal weather without spending a fortune on in-demand hotels and expensive permits if you're happy to swap big-name trails, like Everest Base Camp and the Annapurna Circuit, for quieter treks to Kanchenjunga Base Camp and around the Langtang Valley. Idyllic conditions (dry but not witheringly hot) are also on offer in Rajasthan, one of India’s most vibrant and varied states. Chug between notable, attraction-rich cities like Jaipur, Jodhpur and Udaipur on an atmospheric and wallet-friendly Indian train, snacking on spicy pakoras and sipping sugary chai en route.