Hmmm…this is a tricky one. Since you want to get out of SEA, you might have to go a long way to reach someplace that could be considered cheap and also has decent weather in December. Japan and South Korea will be cold, and not really cheap. If you go south you hit Australia, which is very expensive by most SEA standards (although not bad by Singapore standards). Perth is obviously closest and it’s a real city, and of course Sydney and Melbourne will be in early summer in December so those could work if your budget allows. Brisbane and Cairns are both known for outdoor activities, although nightlife might be tough for teenagers and there are no real cultural sights.

One thing about Cancun that is interesting. Cancun itself is essentially a very long beach sticking out into the Caribbean that is lined with high-rise hotels and time-share properties. Except for a busy area at the corner of that peninsula, most of the hotels are spread out quite a bit, so there aren’t many things that most guests can walk to. Many people love it and are happy to basically stay in their own hotel most of the time, and maybe take a taxi down to that busy corner area once in a while. Personally, I’m a much bigger fan of Playa del Carmen, which is a full-on tourist town about 50 miles south of Cancun. It’s got hundreds of small hotels, restaurants, bars, shops, and everything else a visitor wants. The beaches aren’t quite as nice, but I find the town to be very fun and vibrant. Also, up and down the coast from south of Playa del Carmen to north of Cancun there are large resorts that are far from each other and on huge properties. Many of them are all-inclusive, so that is another option.


More good news comes with the fact that there are two other great resort areas that are each about 90 minutes by shuttle from Montego Bay Airport, so you can almost as easily reach Ocho Rios or Negril, both of which have a different vibe that you might prefer. Bargain hunters will also find pretty amazing prices at the all-inclusive resorts, particularly those in Montego Bay and Ocho Rios. If you prefer a quiet beach area lined with smaller hotels, restaurants, and bars, then head to Negril.
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.
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.
Thank you, and I’m always happy to hear that people find this useful. Buenos Aires is a wonderful city and it feels very modern and very European, at least compared with most of the rest of South America. I would think that bringing a baby there would be similar to bringing one to, say, London or Paris. Rio de Janeiro is perhaps the most beautiful city location on earth, and it’s got some very rich areas (mostly along the beaches) and many dodgy areas. They also seem to struggle more with infrastructure there so bus service isn’t very modern and that sort of thing. That said, I haven’t been since they hosted the World Cup and Olympics and I’ve read that much of the situation has improved. Long story short, I think you might just have to be a bit more careful in Rio when choosing a hotel and neighborhood and that sort of thing, but generally I think you’d be good.
In November you can find excellent resort deals all over the Dominican Republic, but Punta Cana is typically the first choice, especially if you are looking for an all-inclusive resort with all the luxury extras at a great price. The resort is actually a collection of little beach areas on the eastern tip of the island, so it's very secluded and well away from some of the confusion closer to the capital city.
Hotel prices definitely go up in around Christmas so it's best to come early in the month if that's possible, but it's still a pretty good bargain even during the peak weeks. Book early if you can because the better and cheaper hotels will fill up first, of course. Also consider a side trip to the Mendoza wine region, Patagonia, or the amazing water falls of Iguazu.
We are looking to travel somewhere warm in December of this year, for approximately 3-4 weeks. We are originating from Canada – Alberta, to be exact, and have done a fair bit of travelling throughout our lives, however, we are now bringing along our 4 year old son. With that in mind, I suppose our biggest concerns are now flight durations and safety (in our younger years and without children, these weren’t so much a factor, but definitely are considerations now).
From November through February there are literally no European cities that could qualify as having “great weather.” We list Tenerife below because it's technically in Europe, although not really much of a cultural destination. Antalya, Turkey (which technically isn't even in Europe), has the closest thing to a sunny climate with acceptable temperatures. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
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.
In South America, and you start getting into some longer flights here, the best and safest places are Argentina, Peru, and Chile. I’m not sure if this helps you much, but at least it should let you know that you were thinking along the right lines already, and there are no obvious places that you’d overlooked. Let me know if you have any other questions. -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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