Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.
Heat your winter up and pack your backs to explore Australia. Celebrate New Year’s Eve at The Opera Gala in Sydney. Eat your way through the Taste Festival in Tasmania. And if music is your thing, we recommend checking out the Life’s a Beach Music Festival in Rockingham (30 minutes south of Perth) or experience the Woodford Folk Festival in Queensland, one of Australia’s biggest cultural festivals.
Early December is the end of the rainy season in those areas. The storms tend to be short by that time, but still you will probably get a few quick downpours a week. I’m not an expert on getting around in the Philippines, though I do know that it’s rarely fast or easy. If you want a place to relax then Boracay Island might be the best. Sorry I couldn’t be of more help. -Roger
More good news comes with the fact that there are two other great resort areas that are each about 90 minutes by shuttle from Montego Bay Airport, so you can almost as easily reach Ocho Rios or Negril, both of which have a different vibe that you might prefer. Bargain hunters will also find pretty amazing prices at the all-inclusive resorts, particularly those in Montego Bay and Ocho Rios. If you prefer a quiet beach area lined with smaller hotels, restaurants, and bars, then head to Negril.
If you're determined to travel during the holiday periods, though, book your vacation flights, hotels, and cruise far in advance. If it works with your schedule, fly on Thanksgiving Day or Christmas day; those are the least crowded days of the holiday season. And if at all possible, avoid traveling during weekends, on the days right before or after the holiday, and late in the day. It's not only crowded at airports but also northern storms can wreak havoc and create weather delays that cascade across the system.
Even though November is one of the busy months in Pokhara, they've built so many new hotels in the past few years that finding a room – even at a decent price – should always be possible. The high-season rates are still very cheap by almost anyone else's standards, and food and drinks are always very affordable, but if you look around a bit you'll be able to do even better.
I too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
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.
Otherwise the big draws are the Great Barrier Reef, which is obviously focused on diving, snorkeling, and water activities, so it may not be too interesting, and Uluru, which is the big rock in the center of the country (and not near anything else of interest). There is also wine regions in the south near Sydney, and of course nature parks to see kangaroos and the other indigenous animals.
You’ve got a pretty good budget so you can afford to go almost anywhere, assuming you are okay with renting one or two houses or villas instead of 4 hotel rooms. If you are willing to fly all the way to Asia, your best bets would be Bali or one of the Thai islands, probably Ko Samui or Phuket. In all of those places you should be able to rent a house or villa near the beach and then do activities and day trips very easily.
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central.