It looks like you’ve been to most of the more popular options for winter holidays already, and since you listed them I assume you want to go somewhere new. The one that is missing, which I think could be perfect for you, is the Guanacaste area in northern Costa Rica. The weather will be perfect and you should be able to get a reasonably priced flight into nearby Liberia Airport. There are a variety of smaller towns along those beaches, and Tamarindo might be the most famous. They offer a mix of traditional hotels and resorts in smaller towns along with newer 4-star and 5-star hotels on large properties that tend to be away from the towns. The weather will obviously be similar to Panama, as long as you were on the west coast. Costa Rica is the adventure capital of Latin America and one-third of the country is national parks, so there is plenty to see and do. There isn’t much history there, but you can’t have everything.
Sprawled across two countries (Chile and Argentina), Patagonia is one of nature’s last frontiers. For trekking enthusiasts, adventure seekers and nature lovers alike, this remarkable landscape of snow-capped mountain peaks, imposing glaciers, gushing waterfalls, and beautiful national parks is the very definition of ‘epic’.  It’s also one of the most isolated territories in the world, with roughly two people per square kilometre. Here at the end of the world, our planet is at its most wild and spectacular.
I’m sure you’ll have a great time. I don’t have any good suggestions for where to celebrate Christmas, but I’m sure you’ll have no problems finding something by just walking around or checking online. The top draw in Barcelona is the architecture, and especially the 20th Century buildings by Gaudi. I recommend the hop-on, hop-off bus tour because it allows you to see almost all of the famous buildings from the street in just a few hours. Park Guell is worth a visit, but of course the main attraction is the Sagrada Familia cathedral. Check opening times and reserve a ticket in advance if you can.
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
In addition to the obvious perks of pleasant weather and fewer tourists, off-season rates at accommodations are abundant. Voted No. 1 continental U.S. island by Travel + Leisure readers for the third time in 2018, Hilton Head has much to offer visitors. One of the most popular activities, perfect with autumn temperatures, is biking on the more than 60 miles of pathways covering the island, including along 12 miles of beaches. Bird watchers will keep busy spotting egrets, sandpipers, wood storks, sea gulls, pelicans, and ospreys. Well known as a golfer’s paradise, the Hilton Head Island area boasts more than 33 courses.
If you are interested in a place that isn’t focused on beaches in that area then I’ll point you to some recent answers just above where I mention the charms of Chiang Mai in northern Thailand, or Luang Prabang in Laos, and/or Siem Reap in Cambodia. All of those are wonderful places with temples and other sights, and they are quite affordable once you are there as well.
While it's true that it might be a stretch to call Cusco's November weather “great,” this is perhaps the best month of the year to visit, and the weather is quite good anyway. The high season for hotels in Cusco ends in October, yet the rainy season doesn't begin until late December, so November is that perfect combination of small crowds, low prices, and very good weather.
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.
You might also consider Malaysia and perhaps a stop in Singapore. Malaysia is actually more modern than Thailand so everything is easy and reliable. They have cheap VIP buses that are very comfortable. Penang in the north is really nice and also interesting. Kuala Lumpur is a modern and pleasant big city. A bit south of that is the colonial town of Malacca, which is also very nice and worth a look. Going south from there you can reach Singapore in a few hours, and that is an amazing city, although accommodation there is expensive.
As for Costa Rica, I think it would be ideal for what you have in mind. It’s by far the most tourist-friendly (and English speaking friendly) country in that area, so it’s a great starting point. Belize is pretty easy as well, although there is far less nature to enjoy. Panama and Nicaragua are a bit cheaper and have similar things to offer, but Costa Rica has the best infrastructure and nature parks, so it’s less stressful for a first-timer. The snorkeling is better on the Caribbean coast, I believe, but the better tourist beaches are on the Pacific. The country is pretty quick to get across, so you could easily spend a few days on both sides, plus another few exploring the rain forests and volcanoes and such.
Those who find a healthy dose of decadence aids the de-stressing process should make a beeline for UAE capital Abu Dhabi, where infinity pool-rimmed spa hotels offer a taste of the world of the rich and famous amid guaranteed November sun. In Madrid, it’s the laid-back lifestyle of the madrileños that draws travellers, who can browse works by Picasso in the Reina Sofia, quaff Tempranillo in grand plazas and tuck into warming cocido madrileño (traditional chickpea stew), without the stifling crowds of summer.
As for Malaysia, I’m a big fan, and with your friend there it should be easy. Interestingly, I was just in China myself recently and a few days ago I published a long article on my advice for whether to go yourself to China or go on a group tour. I also discuss the most popular and best places to visit when you are there in the bottom part of the article. One tricky thing for many of us is that you have to get a China travel visa and some of us can only get that visa issued in our home country, at least according to their rules. I literally spent years traveling around Asia but I was never able to visit China because they required that I get a visa issued in the US and I had to show my flights booked from the US to China and then from China back to the US. If I could have gotten a visa issued at a Chinese embassy in Bangkok or Singapore, I would have done it years ago.
Me and a buddy is traveling late december, till mid january (about 2 weeks). We’re relatively young and would appreciate a combination of some partying, some beach, and offcourse some cultural input. We were in Bali and Lombok this summer and really enjoyed it. Its great to being able to travel around a little, so that would be a plus for sure:) Right now we’re looking at Vietnam, Goa, and some of the Thai islands. I know the two latter can be quite lively, but how about Vietnam? We’re from Norway, so we need it to be as warm as possible.
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.
I think Sri Lanka would be wonderful for 2 weeks in December. The rainy season typically ends early in December, but even when it’s still going it tends to be quick downpours, as you are no doubt familiar with if you’ve been all over southeast Asia. Still at this point there are very few hostels with dorm beds and not even many cheap budget hotels, but at the age of 30 you are probably happier with normal hotels anyway. Value is quite good in Sri Lanka as long as you can spend at least US$30 or so per night, and hopefully a bit more. Food is also quite cheap in general, although there are still surprisingly few tourist-oriented restaurants in many towns so it feels a bit undiscovered. Just don’t spend much time in Colombo and preferably focus on the mountain areas, and I think you’ll love it.
As you suspected, this is a tricky one. Most of the places that would work for you are having a very rainy month in November, so it’s not a good time. Thailand would actually be a good choice if you can deal with the travel time. The rainy season there ends in October and yet the crowds don’t start appearing until December, so you get low hotel prices with nearly perfect weather. As mentioned, all of the good options in Central or South America have a wet season in November. Argentina could be a good option, as November is late spring there, and it has everything you are looking for. The flights to get there are also fairly long though.
As Christmas approaches the city will fill up much more, so if you can go early in the month you'll be much better off. But even if you can't go before the last week of the month you'll still find Mexico City to be a tremendous bargain compared to pretty much anywhere else in North America. It's a great shopping destination, and not just for goofy souvenirs, so that's something to think about as well.
I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -Roger
December is a popular month to go cruising around Hawaii and Mexico. It’s an ideal family trip, especially with most kids in the US out of school for the holidays. Experience the Hawaii’s tropical paradise. Pick a popular cruise liner and visit ports of call like Nawiliwili on Kauai, Honolulu on Oahu and Kona on the Big Island. If the Caribbean floats your boat, we recommend taking a cruise to explore Mexico’s Costa Maya, Cozumel, Ensenada, Acapulco, Cabo San Lucas, Puerto Vallarta and more.

The only places I’ve visited in Brazil at this point are Rio de Janeiro and the Iguazu Falls area. Both of those areas are very nice and justifiably popular. Aside from those, I hear a lot of mixed things about Brazil. I’m sure I’ll explore more of the country at some point, though I’m in no rush. Among other things, English isn’t widely spoken in Brazil (and in Latin America in general). You might know as much about the country as I do, aside from those places I’ve visited.
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
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