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.
In Central America you could consider Belize. It’s small, but it’s got islands and beaches (not everywhere though) and forests and other cultural sights, and English is more or less the official language. It’s not as well organized as Costa Rica, but it’s not bad and it feels safe. The other to consider there is Panama, which obviously has a lot in common with Costa Rica. It has far fewer adventure activities and the good beaches are spaced out a bit, but still it’s a relatively rich country with tens of thousands of Americans and Canadians living there as well as visiting, so they have a good tourist infrastructure and it’s safe.
Jamaica Montego Bay, Negril, Ocho Rios Martinique Martinique Netherlands Antilles Bonaire, Curaçao, St. Martin/Sint Maarten Puerto Rico Rincón, San Juan Saint Kitts and Nevis St Kitts Saint Lucia St. Lucia Trinidad and Tobago Trinidad and Tabago Turks and Caicos Islands Turks and Caicos Virgin Islands, British Tortola Virgin Islands, U.s. St. Croix, St. Thomas
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central.
You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
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.
Hey Roger. My girlfriend and I are planning to go during Christmas for 13 days from San Diego, CA to South America mainly on the west side. We are not up for beaches but rather historical, adventurous, and scenic places. We are keen on Cusco (Peru) (Inca Trail), Quito (Ecuador), Costa Rica (Rain Forest), Bogota (Columbia). Please can you help us with your expert advice on which cities are a must for first timers to South America. We are not picky and simply want to have a fun time. Thank you for your time.

My second vacation meal was dinner that night. After walking almost ten miles at the park, the hotel, and spending the late afternoon swimming in the pool, we did dinner at the hotel restaurant before heading back to the park to ride a few things one last time. Dinner (Meal 2) consisted of pot roast with carrots and mushrooms (I asked them to go light on my carrots and they did a very good job of it), and a side salad that I again topped with salt, pepper, and blue cheese dressing.
Lace up your boots for an end-of-year adventure at the wild ends of the Earth. December is the ideal time to explore Patagonia’s mind-blowingly beautiful Torres del Paine National Park. Embark on an epic trek along the eight-day circuit, or take the four-day ‘W’ trek for Instagram-worthy views of Los Cuernos (the ‘horns’), the region’s iconic jagged granite peaks. Similarly breathtaking experiences can be had diving the coral reefs around Thailand’s Similan Islands. Beneath the sparkling surface of the ocean you’ll find sharks, barracuda, rays and green and hawksbill turtles – it’s Finding Nemo brought to life.
Unlike most cities on South America's west coast, Buenos Aires has fairly consistent rainfall all year long, and you might see a bit of the wet stuff even during December. Still, the temperatures should be ideal for being outdoors, and this is really mostly an indoor city anyway, so when it does rain you'll be able to pop into a shop or museum or cafe and have a great time.

When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
Picking your next destination isn’t easy, but there’s a better way than spinning a big globe, closing your eyes and slamming your finger down (it’ll probably end up in middle of the Atlantic, and wifi there is patchy to say the least). Introducing our ultimate month-by-month destination guide: your no-fuss list of places to go, things to see, and good weather to chase around the world.
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
November is a month of transitions: weather is cooling in most places, and as the days move towards Thanksgiving, momentum picks up and we’re rushing headlong into the winter holidays. It could be a good time for a trip, whether you’re looking for warm weather, taking advantage of cheap shoulder season rates, exploring a new exotic destination, or heading to the southern hemisphere to trade autumn for spring. Or you just might want to begin the holiday season early, get a head start on gift shopping, and jump right into winter’s chilly weather. Travel during November has something for everybody.
If you book a resort hotel from home you'll probably think Goa hotel prices are much higher than you were expecting, but if you book a family-run place once you arrive you'll still find fantastic bargains. It's probably wise to book a few nights online before you get to India, because it can be incredibly confusing at first. After that you might be able to find a similar place for half the price by just checking around the same area.
Few people travel between Thanksgiving and Christmas—specifically, from the Tuesday after Thanksgiving to the Thursday or Friday before the peak Christmas rush—so you can enjoy substantial savings off peak-season rates (four nights for the price of three, seven nights for the price of five) and your chances of an upgrade are good—if you book through a Caribbean specialist with clout.
Australia’s capital has been voted the world’s most livable city—for the seven years in a row. If that isn’t reason enough to go, what is? Here's another: the artsy cosmopolitan city promises pleasant temperatures in the high 60s throughout November. Book a room at one of the area's buzziest spots, QT Melbourne, a design-centric boutique in the city’s fashion district.
As with other Caribbean resort destinations, the weather in Montego Bay is perfect in December, and the first half of the month is still cheap for flights and resort prices. The weekend before Christmas is when peak season here starts, and if you book early enough you can still get a good deal then, but don't expect many last-minute bargains during that period.
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.
This classic Thanksgiving side came from Julia Child. We don’t see many creamed vegetables any more, except maybe creamed corn or spinach, so this might be a bit of a novelty. And it’s delicious. If people complain about the richness, just remind them that Thanksgiving dinner is supposed to be a feast, right? (And you can get by with an awful lot be invoking the name Julia Child).

Even when those quick rain storms come, you can see them forming and head indoors for a while. Nearly every hotel on Boracay is on the beach or within 200 meters of the beach, so it’s really easy to stay dry. If you stay along White Beach (where most hotels are) I think it would be easy to meet other people if you choose as well. Let me know if you have any other questions. -Roger
There are not one but a cornucopia of hotspots to check out in the Aloha State come November. First, Oahu, which has, throughout the years, been transformed by Asian-Pacific locals from a holiday outpost into a globalized, cosmopolitan destination that offers all the glory of paradise in one locale. You’ve got the allure of the Island landscape, plus the buzz of modern living mixed in a relaxed, slow-paced daily lifestyle near the shores. It is (along with Honolulu) the center of the Hawaiian universe, and will no doubt sprinkle excitement into any Thanksgiving celebration. You might even want to go all out by getting a taste of authentic, fantastic Hawaiian flavor by cooking that turkey in a traditional imu (underground oven)! Those who want to work off all that feasting can hop on into the Turkey Trot 10 Mile Run on Thanksgiving morning and then spend Black Friday enjoying the annual Waikiki Holiday Parade—instead of braving those restless shopping crowds.
Australia’s capital has been voted the world’s most livable city—for the seven years in a row. If that isn’t reason enough to go, what is? Here's another: the artsy cosmopolitan city promises pleasant temperatures in the high 60s throughout November. Book a room at one of the area's buzziest spots, QT Melbourne, a design-centric boutique in the city’s fashion district.
Australia is so large and varied that one cannot simply say ‘go to Australia in November’ and expect everything to be fine beachy. That said, November is probably as close as it gets to being perfect weather country-wide. The tropical rainy season in the North hasn’t properly settled into humid downpours yet, while the cooler southern states of Victoria and Tasmania are shaking off the winter frost and basking in warmer days. Vino and meals are taken al fresco, outdoor music and food festivals pop up everywhere, and beaches across the country begin to buzz.
On the hunt for a non-traditional ski vacation? Look no further than the Japanese Alps. According to American Express Travel, the region has seen an increase in bookings during the holidays in recent years. And while December has historically been less popular than Japan’s peak season—April-November—adventurous travelers are now intrigued by the wilderness of Japan in the winter. The Hida, Kiso, and Akaishi alps are home to indigenous snow monkeys, volcanoes, and lava plateaus, plus, visitors are drawn to the area for its pristine ski offerings, natural hot springs, and rural hiking.
And if you are mostly interested in adventure and nature rather than cities, you might also consider India. The cities in India are complete insane asylums, but once you get outside of them it’s a beautiful country. The area of Kerala and its backwaters are a big highlight. They’ll remind you a bit of Sri Lanka in some ways, although things are cheaper and the scenery is quite different. The various beach areas of Goa, just to the north of Kerala, are also worth considering.
I know what you mean about how easy everything is in Thailand, with a 7-Eleven on every corner. But I don’t know the current visa situation because it’s changed recently and might change again. Still, I think they are mainly trying to cut off the people who try to stay forever on consecutive Tourist Visas, and they are still welcoming of the 60-day visits. I hope so anyway because I might be heading there this winter myself.
As for flight connections, Barcelona and Madrid should have decent connections to Toronto and Delhi, while Casablanca (Morocco’s largest airport) probably does not. So Spain is the better choice by that standard. On the other hand, you can get to Morocco by ferry from Spain in a short time, so you could go to Spain and also visit Morocco for a day or two. 
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