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.
Never thought of Moscow as a Winter destination! It is quite the place to go especially after the world cup hype. I second Rajasthan, India as one of the best places to travel in December. Love this list, Wendy. I have even listed Rajasthan and other offbeat places to travel in December and January over here: https://www.thegonegoat.com/inspiration-and-tips/2018/11/29/the-best-places-to-travel-december-january
As for Malaysia, I love it there too, but it has very few nice beaches in the main part of the country (not including Borneo). But now that you mention it, they do have some nice beaches in Penang, which is the best tourist area anyway. If you search for hotels in Penang, make sure that they are on or very near a nice beach. Most of the island does not have sandy beaches, but some parts do.
Once again, it's worth noting that the first half of December will be cheaper and far less crowded than the time around Christmas, so if it's possible you should come early for best value. Still, compared to, say, Miami Beach, Cancun and the other Mexican resort towns are far cheaper and at least as fun as well. By the way, Cancun is mainly just a strip of high-rise hotels along a lovely beach, while Playa del Carmen (about an hour south) is a real tourist-friendly town with smaller hotels as well as hundreds of restaurants and shops to choose from.
Portugal does have one of Europe’s best autumn climates, but as you’ve noticed November can be a bit rainy. That said, in my experience it rarely rains for long periods in that part of Europe so I think it’s very unlikely that a big part of your trip would be “rained out.” Also those cities have lots of great indoor attractions so if you see that it’s supposed to be clear in the morning and drizzly in the afternoon, you can plan to explore neighborhoods in the morning and plan to visit a museum or castle in the afternoon. It’s a bit of a crap-shoot and generally Portugal has nicer weather than most of the rest of Europe at any given time. I hope this helps. -Roger
If you are looking for first-rate destinations that are among the cheaper European cities, I’ll suggest Prague, Budapest, Krakow, and Berlin. You could visit all four of them by taking trains, or choose any one, two, or three. In December you can get quite a nice room in any of those cities, with Berlin being the most expensive by a bit. Food and attractions are also quite affordable in those cities.
If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.