Much of Mexico is ideal in December, after the rainy season has ended; if you go early in the month, you’ll avoid the peak holiday-season rates that kick in around December 18. On the Pacific coast, the landscapes are still ultra-tropical green, and the ocean is bathtub-warm (80s), with exceptional clarity for scuba diving and snorkeling. Mexico City is a smart place to spend the holidays, when the locals have headed to the beach and you’ll find much less traffic in this famously congested city. (Do keep in mind, though, that some of the more sought-after restaurants and galleries will be closed.)
Since you’ve been to several of the top places in Asia already, and you love it, I think Bali might be your best bet. As I’ve written many times recently, I feel that the main tourist area of Kuta/Legian/Seminyak is just too crowded and overdeveloped to recommend, although it is interesting for a couple days and some nightlife. The arts and crafts town of Ubud is still nice, although also a bit crowded, but it’s not anything like a city so I still think you’d enjoy it.
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger
The traffic in Bali makes sightseeing notoriously challenging in June through August, but November is less crowded so it's a good time to come and spend a day in Ubud or even take a tour of the towns along the northern shore. In fact, if you want to avoid the huge Kuta crowds altogether you should consider basing yourself in the Lovina area of the north shore. It's as lovely and charming as the whole island was 20 years ago, but that may not last.
It's been said Jackson Hole is where Aspen meets Palm Springs. Ski season, however, really starts in mid-December. There's world-class—not to mention some of the most vertiginous—skiing in the continental U.S. Plus, miles and miles of trails and nature to enjoy less vertically trekking through Grand Teton National Park and Yellowstone National Park. To put much of this at your fingertips, the Four Seasons Jackson Hole has a ski concierge and is a ski-in/ski-out property.
Venice can get pretty cold and they also have those famous Acqua Alta floods in winter, so read up on that before you go. But Rome and Munich should be easy to visit in December. One suggestion I will make is to consider visiting Rome for 3 or 4 nights and then base yourself down on Sorrento for the remaining 2 or 3 nights. Rome is one of those cities that is crowded and chaotic even in winter, to the point that just crossing the street can be frustrating, so many people get tired of that after they’ve seen the main sights. And Sorrento, on the other hand, is a lovely small city that is close to Amalfi, Pompeii, Naples, and the Isle of Capri, so it’s an ideal base to visit all of those. Sorrento is also cheaper than Rome, and a surprising number of locals speak English there, so it’s easy and pleasant. That time of year I’m not even sure if the tourist buses are running to Amalfi, although the local ones will be.
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.
The 2nd option is a bit early in the year. The Greek Islands are cold and mostly deserted until mid April or so, and the good weather really starts in May or June. This is true in Mallorca as well. The Canary Islands are much farther south so they have acceptable beach weather almost all year, although you might get some cooler days in March as well. Even still I wouldn’t really recommend them for a younger person. In my opinion, the Canary Islands are pretty boring because the majority of visitors that time of year will be retired people from northern Europe who just want to sit in the sun. The nightlife tends to be cheesy and/or weak if you can find it at all. Let me know if you have any other questions. -Roger
Since you mention the temperature in Fahrenheit, I’ll assume you are in the United States. You might have to go to the Southern Hemisphere to reliably get 84F or higher, but you can get over 80F in most of the Caribbean. You’ll get low 80s in Hawaii in early December as well. Fortunately, neither of those places get too crowded until just before Christmas, so either should work.
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
The rainy season is over so it's an ideal time to base yourself in Chiang Mai for some outdoor activities in the area. There are temples like crazy in the city center between the old walls, but even more interesting ones in the area just around Chiang Mai. There's also great trekking and such, available quite affordably from any travel agency in the city.
That really depends on your starting point. Most of the cheapest places are in Asia, but the flight would be quite expensive if you are in North America or Europe. If you are in the US, your best bets for cheap places with good weather that time of year will be the non-resort towns of Mexico, or even the resort towns if your budget is a bit higher. Let me know your starting point and more about what you are looking for and I can give you a more complete answer. -Roger
From the Art Deco architecture to fabulous restaurants and nightlife, Miami is truly a city that appeals to every type of traveler. Art and culture lovers should plan a trip during Art Basel, which officially kicks off on December 6. The weeklong affair attracts celebrities, tastemakers, and bold-faced names, who come for the world-renowned art exhibitions, but stay for the swanky parties and events. Be sure to book a hotel well in advance, as prices skyrocket and availability becomes increasingly limited.
Also, as far as I hear, the worst that ever happens is they take your stuff. So if you leave your passport and most of your money in your hotel room, and keep your phone or camera hidden most of the time, there isn’t much to lose. I’m making it sound worse than it is really. I wouldn’t hesitate to go to Rio again, but of course I’d be aware of those few situations to avoid.
Aside from Indonesia you might also consider Thailand, which has great infrastructure so it’s much easier to travel with young children. Phuket has by far the most options, and its rainy season usually ends in early November. For families I recommend Kata Beach and Karon Beach, which are both just south of the main shopping and nightlife town of Patong Beach.
Actually, all of my best suggestions for those things are in the article above. One challenge you’ll have is that all popular tropical destinations have their peak weeks at the end of December because so many people in cold areas have that time off. So flights to Central or South America are going to be fairly expensive, although buying soon can help. For hiking and views I think Costa Rica could be a good choice, or Nicaragua. You could also go to Bariloche in Argentina, though it’s probably not worth going all that way unless you were also going to spend some time in Buenos Aires and such.
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.