When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
Thailand is far more different and it’s easier to get around. The tourist areas are quite modern and well organized, and enough people speak English that it’s easy to do whatever you like. Again there you have choices of cooler areas in the north such as Chiang Mai, and of course Bangkok, as well as all of the islands. Let me know if you have any questions. -Roger
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.
Visitors travel from around the world to experience Nuremberg's iconic Christmas Market. "Christkindlesmarkt," as it's called, is a tradition that dates back to 1628 and features more than 180 stalls. Though you could easily spend several days wandering the market, there are plenty of other things to see in the area, namely museums—Nuremberg is home to 43 of them.
My two years in southeast Asia was over a few trips, although I did have my own apartment in Bangkok for 3 months and in Chiang Mai for another 3 months. As an American I didn’t have a national health restriction and I didn’t even have travel insurance. I don’t recommend it for everybody, but healthcare in those areas is extremely cheap and of pretty good quality. I went to a hospital once in Chiang Mai and I saw an English-speaking doctor for about US$7, and spent another US$25 or so on a prescription. My longest total trip was 3 years and 7 months (only a few years ago), and I went in and out of Southeast Asia a few times in that period.
The “city that never sleeps” is a delight in December, even if the weather makes it necessary to bundle up a bit. For holiday spirit and things to do any time of year, New York City is a top destination. Broadway and off-Broadway shows are exceptional entertainment, and the Radio City Music Hall Christmas Spectacular with the famous Rockettes is a perfect holiday event. The New York City Ballet at Lincoln Center presents the classic "Nutcracker," a seasonal tradition. At the New York Botanical Garden, the toy train will wind its way through a miniature Lower Manhattan for the amusement of kids as well as nostalgic adults who may have once had their own train sets. The dazzling Rockefeller Center Christmas Tree, New York City’s centerpiece each year with nearly 50,000 lights, will once again overlook the famed ice skating rink and golden Prometheus statue. Window shopping takes on new meaning during December when department stores along Fifth Avenue entertain passers-by with intricate decorations and displays. Holiday markets at Bryant Park, Columbus Circle, and Union Square also invite browsing and shopping along with warm drinks and food. For a convenient stay, the Renaissance New York Midtown Hotel offers spectacular views and Versa, a year-round rooftop restaurant and bar. Or enjoy the Innside by Melia New York in the trendy Chelsea area with its newly opened seafood-focused dining spot, The Wilson.
If you didn’t want to go to Asia you could instead consider the ABC islands, which don’t get much rain and haven’t had a major storm in many decades. Aruba, Bonaire, and Curacao are known for good snorkeling as well and you’d get good hotel rates that time of year. Two weeks might be a long time to spend on those islands though, so I would go to Asia if you can. Late November is a perfect time of year for a visit there, and you can even include a few days in Siem Reap to visit Ankor Wat. Let me know if you have any other questions. -Roger

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.
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