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Christmas markets sprout up all over the country this month, and from the smallest towns to the biggest cities they’re a great place to mingle with locals, learn about regional handicrafts, and sample seasonal delicacies. Depending on the venue, you can find anything from medieval reenactments to outdoor concerts. But they’re usually at their prime once darkness has set in and the fairy lights are out in full force (which means there’s also time in the day for museum visits and city touring before indulging in the market flurry). Some travelers skip dinner altogether for a smorgasbord of yuletide samplings at the wooden market huts!
I’m happy to try to help. It’s hard to say whether one 30-day trip would be better than several shorter trips. On one hand, it’s much more efficient to go for a month because it obviously saves you all the going back and forth. Also, one week is a short time to go 7 or 8 time zones away, as it takes pretty much an entire day each way, and at least a few days to adjust to the time change. Hmmm…

I haven’t followed the Zika list, but I do understand the concern. Since you aren’t big beach people, you might just bring jackets and go to a more romantic city like Paris, and then maybe down to Nice for part of the trip and something a bit different. I’m not sure if this is helping, but if you have any questions about any of this I’m happy to keep trying. -Roger 

Without knowing more about your interests, my top suggestion would be to focus on Sydney and Melbourne and the areas around both. The Blue Mountains near Sydney are also nice for a couple days or so. The main challenge you’d have in seeing a lot of Australia is that it’s all so spread out. You can hire a car for Melbourne and Sydney and that whole area, but it’s better to fly to get to Uluru (near Alice Springs) or Brisbane or Cairns/Great Barrier Reef or Perth. You’d be driving for days in between those places if you started from the southeast area where most people live.
If you are looking for beach weather in December then most of your list won’t work, and several of them are only on rivers. Starting from Kolkata you have many good choices that are much closer to you than anywhere in Europe or the Canary Islands, or the Caribbean for that matter. In fact, I’m a bit confused by your list because there are so many different types of places on it, many that aren’t warm or on beaches.
Surprising to some people, December can actually be a bit cool in Mexico City, especially at night. Its elevation keeps it mild all year, but at least the rainy season is totally over by December, so it's an ideal month for a cheap cultural holiday, perhaps combined with a trip to one of Mexico's many beach resorts. You can get cheap flights between Mexico City and Cancun or Puerto Vallarta, for example.
A visit to Vienna in December might be a holiday experience of a lifetime. From the festively adorned palaces, magical Christmas markets, classical concerts, and choirs to the cozy cafes and restaurants, the surreal atmosphere seems like a Hollywood movie. With nearly a dozen Christmas markets to choose from, the one in front of City Hall is notable for its giant tree, ice skating rink, carousel, and reindeer train. At another in Freyung Square, you’ll find delicious mulled wine, gingerbread, roasted chestnuts, and a variety of regional snacks in addition to jewelry, handmade toys, candles, and more. The market at Spittelberg, set amidst lovely townhouses and narrow streets filled with bars, restaurants, and galleries, is a wonderful place to sip champagne and browse the many shops. Set in front of the world famous baroque residence, the Christmas Village at Belvedere Palace should not be missed. Book a Christmas concert at the renowned Kursalon where Johann Strauss was the concertmaster or enjoy a recital at one of the many distinguished churches through Vienna. You can even take a walk or a “hop on, hop off” bus to enjoy the Christmas displays. No winter night is complete without a stop at a sausage stand for a succulent bratwurst served with mustard, horseradish, and a classic bun. In the heart of the city, the magnificent Hotel Grand Ferdinand would be the perfect home base for exploring Vienna.
Of the others, I’d say that Thailand would probably be your better choice. Goa is obviously famous for its beach parties, and drugs are easily available there just in case that is important, but there really isn’t much else to see or do there. Goa is a collection of beach towns, some of which are filled with raucous Westerners all winter. But once you go inland, it’s kind of falling apart, and it’s not even very “Indian” because it was run by the Portuguese until about 60 years ago.

As far as finding work on the road, the only decent-paying job that is fairly easy to get that I’m aware of is teaching English, but I think those gigs tend to last at least a few months. Right now Thailand is trying to get rid of any foreigners who are working in hotels and bars without permits, so Cambodia might be better at the moment. I’m one of the thousands of people who work online while traveling, and it seems much easier to make a decent living that way compared to working in hostels and such. Good luck with whatever you decide, and maybe I’ll see you on the road at some point. -Roger
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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