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 great thing is, many hotels that have rooms with kitchenettes don’t charge more (or it’s minimally extra) than what a normal room would be. Be sure you call in advance to make sure you’re getting a full kitchen. We spent one night at a hotel that claimed they had a kitchenette, but it was really only a dorm room size refrigerator and a microwave.
As chilly temperatures arrive in the northern hemisphere, it’s spring in Buenos Aires, an ideal time to visit. The city’s jacaranda trees are decorating the streets in purple petals, hotel prices are attractive, and the weather is comfortable and dry. A cruise along the Rio de la Plata would be a good place to start, for a relaxing overview of neighborhoods, homes, markets, and the waterfront. On Sundays, get some authentic local flavor at Feria De Mataderos, about an hour from downtown, with gauchos on horses, craft vendors, musicians, tango dancers, and regional foods.

Hotels in Buenos Aires are starting to reach their summer peak prices in November, especially toward the end of the month, but still they are a fantastic bargain by European or North American standards. The weather in November is also pretty much perfect, and while there's always a threat of rain in BA, it's mostly an indoor city so it shouldn't be too much of an inconvenience.
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.
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.
If this were last year I might have also suggested San Juan, Puerto Rico or Cartagena, but both of those have issues at the moment. If for some reason you don’t like what you see in Costa Rica, there are also some really nice resorts in Panama, especially in the San Blas Islands area. Aside from those you’d probably have to fly longer than you prefer. I hope this helps. -Roger
For those looking for an even calmer slice of paradise without all the holiday festivities, try Waimei on Kauai’s southwestern shore, which offers calm waters and sandy beaches that are especially attractive in the early winter months. Get away from all the gloomy weather of the East Coast by trying out a Waimea vacation rental—it’ll definitely make for makes the perfect base to explore all Kauai has to offer.
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.
I’ve spent a few weeks on Boracay, but not in early November. From what I’ve read, the monsoons there are usually not too bad, and it’s mainly a matter of a couple of hours rain in the afternoon on the bad days. Throughout the Tropics it’s very rare to get rain all day on any given day, and I’ve spent many months in those areas during rainy seasons. So early November isn’t ideal, but if it’s the only time you can go I still think you’ll enjoy it. One nice thing about Boracay is that the hotels are all basically on the beach or right off the beach, so even if it does start raining you can be back in your room in like 2 or 3 minutes. Best of luck with this. -Roger

Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger
You still get warm ocean breezes and 70-degree temperatures, plus the Hawaiian islands go all out for the holidays. Locals host potlatch-style parties where the Christmas goose is replaced by a luau pig, and the resorts deck themselves out like tropical North Poles, including a massive tree-lighting ceremony at the Outrigger on Oahu and tree-decorating contests at Mauna Kea on the Big Island. Residents there climb to the top of the 13,000-foot-tall volcano, shovel snow into their trucks and speed back down to build snowmen in their yards before it melts.

If you’re dreaming of a white Christmas, head to Tallinn to see the medieval city decked out in a blanket of snow, complete with flickering candles lining the streets and markets flogging quintessential Christmas curiosities and festive treats. And if that’s not enough seasonal charm for you, make for Rovaniemi in Finnish Lapland, the ‘official home’ of Santa Claus. Once you’ve dropped your gift list off with the big man himself, treat yourself to a husky sledding excursion or reindeer safari to explore the region in full effect.
Thank you for the kind words. If you’ve got 30 days in Thailand I would recommend spending more time in Bangkok and probably in Chiang Mai as well. Bangkok is huge and in December the weather is actually quite nice, so two days seems way too rushed. As for which islands to consider it sort of depends on why you don’t want to go to Phuket. Phuket is the largest and busiest island and it’s got just about everything that the rest of the islands has. I can understand not wanting to spend time in Patong Beach, which is the shopping and nightlife capital, but there are many other wonderful beaches and towns on Phuket that are quite different from that.
If you are referring to days trips and that sort of thing, it will be much cheaper if you book once you get there. In Vietnam in particular it’s amazing how cheap tours can be if you book them through your hotel. I once did a 6-hour bus tour to Mỹ Sơn, which is near Hoi An, and I think I paid about US$6. It even included a boat ride and a basic lunch. That same day tour online would probably cost US$30 because the booking company takes a share and there is very little competition.
Interestingly, December though February do get a bit cool in Cairo, so it's not a great winter break, but in November it's still pleasantly warm and bone-dry so you can enjoy the outdoors for long periods of time. If you don't mind staying in a locally-owned hotel you can save a lot of money and see some old-world charm at the same time. Reservations in advance aren't necessary, but it's best to book your first couple of days just to avoid all the confusion once you arrive.
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

Eat Breakfast In – I know this isn’t always possible, and it’s certainly not a deal breaker, but we ate breakfast in most mornings. This started my day off on the right foot, and I could make my eggs exactly how I like them. I didn’t get tired of eating bacon and eggs all week, but if you do there are so many keto breakfast options if you’d prefer a variety of foods. For me, this was budget friendly, and I didn’t have to buy a ton of extra groceries. Also, I have a big family with two of my four kids being 3 and under. It takes us forever to get out, so cooking breakfast is an easier option for us. If you’d rather eat out, I get it! Keep scrolling for other helpful tips.
Another option is Thailand, and Phuket has the most family-friendly beach areas. You could get a family hotel room at one of the many beach resorts that has a Kids Club in addition to swimming pools and the beach itself. Those are my top suggestions for a family trip that is also suitable for an anniversary. I hope this helps. Let me know if you have any other questions. -Roger
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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