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.

November brings the annual Vodafone Mexefest Music Festival (Nov. 24-25), a gathering of popular artists in venues throughout Lisbon. The Lisbon & Sintra Film Festival, in its 12th year, is a celebration of cinema with directors, actors, artists, musicians, and writers in town for the event (Nov. 16-25). Billed as the “largest technology conference in the world,” Web Summit began in 2010 as a way to connect industry and the technology community (Nov. 5-8). The year’s new wine and the ripening of chestnuts are celebrated with the Magusto, on Nov. 11, St. Martin’s Day. The holiday spirit becomes apparent at the end of the month, with colorful lights and roasted chestnut vendors along the streets.


My top recommendation would be San Juan, Puerto Rico. It offers a wonderful mix of history and culture and nightlife and great food, alongside excellent beaches and abundant activities. Hotels and rental apartments are mostly in the mid-range for the Caribbean, but food and drinks and most other things are great value. You could get a place in the Condado area, which is close to the lovely Old San Juan neighborhood and plenty of nightlife all around. And then perhaps you could rent a car and stay for a few days at one of the smaller beach towns elsewhere on the island. You wouldn’t even need a passport, although it does feel fairly exotic while you are there. But because it’s part of the US, it’s also well organized and safe. Most people you’ll meet will speak at least some English, and many are fluent, so it’s easy even if you don’t speak Spanish.
Your Munich plan sounds good. It can be fun to actually spend a full night in a town like Rothenburg ob der Tauber because it’s filled with day-trippers in the day and you almost have it to yourself at night. But it’s small enough that one night there would be enough. Nuremburg is quite a large city, and you might even stay there a night or two as well. I don’t know if I’ve ever heard of anyone saying they enjoy the cold and the rain, but if you do you’ll love it there. Fortunately, nowhere in the popular parts of Europe do they get extreme winters, and there is a good chance you won’t even see any snow in those cities. Most people are looking for the warmest places, which can be found in Portugal and Spain, but since that isn’t you I think your plan is good. Christmas is a big deal in some European cities such as Rome, but not a huge deal in others. Most businesses will be closed that day in nearly all countries, but of course hotels and many restaurants will be open. I hope this helps. Let me know if you have any other questions. -Roger
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While Cancun has become the king of the Mexican beach resort towns in the few decades since it was formed, it's only one of many, and all of them on both coasts have very nice weather in December. In fact, Cancun is probably the most expensive of them, so especially if you are coming from the west coast you are better off in Puerto Vallarta, Acapulco, or Los Cabos instead.
On my own trip I spent 3 nights on the North Island after leaving Auckland, and then 4 nights on the South Island. The South Island is more scenic and interesting, and much less crowded, so I would have liked to have stayed another 2 or 3 nights if I had the time. So I’d recommend 3 or 4 nights on the North Island and 5 to 7 nights on the South Island. With smaller towns and smaller crowds on the South Island, that is the better place for star gazing, though most of the North Island is fairly empty as well. It’s an amazing place and I’m sure you’ll love it. Have a great trip. -Roger
New Zealand will also be crowded, but the country is otherwise mostly empty so it is still wonderful. You could fly to Auckland for one day or so and rent a campervan/motorhome. Drive it for 3 or so days on the North Island, and then onto the ferry to the South Island for the rest of your time. The South Island is far more scenic and less crowded. You’ll be doing some driving and looking, but after a few hours of that you can stop at a campground and have plenty of things to do such as hiking or water sports and much more.

Needless to say, Australia is a huge country so you could spend 6 months there and not get bored, or you could spend one week there and barely see any of it. The obvious destinations are Sydney and Melbourne, both with plenty to do for non-beach people. Melbourne is known a bit more for culture and food, while Sydney is more pleasant and still very interesting. There is also the Great Ocean Road, which is a very scenic drive just a bit south of Melbourne.


Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.
If you know where you’re going far enough in advance, you can contact your resort or vacation destination and explain your dietary needs with an employee. The vast majority of destinations, including ours, are opening up their menus to try and make them more friendly to those with food allergies and special dietary needs. While keto/low carb aren’t always on those special menus, the fact that they have special menus at all shows that vacation spots recognize that there are a lot of different dietary needs and are willing to help people who can’t or won’t eat the standard fare.
The last suggestion would be to start in Bangkok, which is an amazing city even if you avoid the Khosan Road party area, and then head south along the coast and into Malaysia and finally Singapore if you feel like it. There are many nice beaches and islands in Thailand that aren’t filled with party folks, and some really interesting places in Malaysia as well. George Town on Penang is really nice with excellent food, and Kuala Lumpur is my favorite city in Asia for few reasons. The town of Malacca is really nice, and Singapore is amazing, if a bit expensive.
Plus, Colorado is home to the world-renowned Breckinridge, a historic town at the base of the Rocky Mountains’ Tenmile Range that’s well-known for its ski resort, year-round alpine activities, and Gold Rush history. You’ll also find tons of shops, galleries, and restaurants housed inside colorfully-painted Victorian buildings, along with four whole mountain peaks that provide 2,358 acres of enough variety to suit even the most seasoned of skiers, boarders, or even snow-shoers. It’s also important to mention that last season, the Summit County municipality saw 447 inches of snow. Lifts open up in November, so what are you waiting for?!
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.
If you are looking for something far less developed than Phuket or any other Thai island, Boracay might be for you. This gorgeous strip of sand is a bit out of the way, but partly because of that it still feels only partly discovered. You'll spend your days relaxing along White Beach or walking up and down the sandy paths that serve as the only real form of transport for most people. Many visitors come every year, and quite a few of those never seem to leave.
Cartagena is a lovely place as well, but another reader just pointed out that the US government has a new travel warning to all of Colombia as of June, 2017. The US has travel warnings to many countries that people still safely travel to every day, but it is something to consider. Many years ago Colombia had quite a few problems, and yet Cartagena was always okay because it is this little cruise port and tourist city far away from the major urban centers. Seeing this, I would think twice myself, although I wouldn’t rule it out, but I also wouldn’t go anywhere except Cartagena at the moment.
With a vibrant downtown, great restaurants, culture, and a recent multi-million renovation to the Ritz Carlton, Naples, one of the areas most luxurious hotels, December is when the town really starts to get into gear. You can spend your time on the miles of gorgeous Gulf Coast white sand beaches, take an Everglades Safari, or head to the Artis-Naples which hosts world class dance, theatre, music, and comedy. And that is to say nothing of the five-star shopping.
December is the end of the rainy season in Boracay, but by the middle of December you would probably only get a few quick tropical showers a week. Room rates are a bit lower at that time as well, so it can be a great time to visit. If you were looking for a place to go for 2 or 3 days, I wouldn’t recommend it because it does take some time to get there and you could be a bit unlucky with the rain. But if you are going for longer than that I’d highly recommend it. It’s a wonderful little island that feels like you’ve gone back in time to before mass-market tourism in places like Phuket.

This year I’ve based myself in Miami, USA, primarily so I can visit many places in the Caribbean that I hadn’t been to before. I just got back from a week in Jamaica and soon I’m going to Puerto Rico, Dominican Republic, Panama, and Colombia, as mentioned. But in December I’m hitting the road again and I’ll be in Asia for the winter and probably in London for much of 2016. Sorry I don’t have more specific information to help you plan your trip, but it sounds like you’ve got some really good choices already under consideration. And I’m sure you’ll have a great time. -Roger
Sri Lanka doesn’t really have a good infrastructure for budget travelers at this point. There are loads of nice hotels if you are willing to pay US$40 or more per night, but almost nothing below that except for a few hostels. I haven’t been to Palawan but I have been to Boracay and Palawan can’t be too much cheaper. Boracay doesn’t have many budget options either, so my guess is that Thailand or Cambodia is your best bet.
December is the month when stores and streets are decorated for the holiday season, reminding us that we have lots to do, whether it’s gift shopping, travel planning, or finding the right outfit for a party. Savvy travelers know that the early weeks of December provide a perfect opportunity to take a trip. With nearly everyone absorbed in getting ready for the holidays instead of traveling, airlines and hotels are offering great deals. Others might want a change of scenery or a chance to celebrate the holidays in a new faraway place.
Hello Roger, we thats me, my wife, our 2 year old daughter and parents inlaw are planing our december vacation. Our starting point is philippines. We have been to thailand last year and are looking at vietnam , cambodia or laos for this year. We are not much for beaches and party but we like culture, history and beautyfull landscapes and warm weather and good food. We are greatfull for ideas and tips that point us in the right direction. Thx a million.
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