My best recommendation would be somewhere in the islands of Thailand. December has very pleasant weather with warm days and nights that can be a bit chilly (for some people). Best of all, it’s a very beautiful place and the tourist infrastructure makes it easy to get around speaking English and with very few headaches. The largest island is Phuket and it has famous nightlife in the Patong Beach area. In fact, the nightlife is so notorious that many people think it’s too much so they avoid the place. There are many other beach areas that are quiet and still close enough to go into Patong once in a while.

In India I’ve always had good luck with the trains by booking at least a couple days in advance, and also being flexible and only going when an AC3 ticket is available. As you know, the actual train stations are nightmares. But every hotel has a person who can fetch a ticket for you by going through the back door and bribing someone at the train office. Like a AC3 ticket might cost US$20, and for an extra US$4, your hotel will go buy it for you and it’ll be waiting at the front desk later that day. It’s a pretty sweet system.
A charming, historic city to visit any time of year, Edinburgh is especially festive during December. Walking through its cobblestone streets takes you back to medieval days when sheep, cattle, and grain were sold in what is now the center of the city. Today, the Royal Mile includes shops, cafes, and museums. Edinburgh Castle, a must for first-time visitors, dates to the 12th century, with its dramatic silhouette overlooking the city. For those seeking holiday celebrations, the Royal Botanic Garden is decorated with lights, music, and illuminated trees. European-style Christmas markets pop up at Princes Street Gardens and George Street, offering traditional crafts, gifts, food, and warming drinks, most welcome during chilly December. The annual Hogmanay celebration welcomes the New Year with fireworks, food, and festivities. Don’t miss the delicious and ubiquitous fish chowder called “Cullen skink,” and be sure to try haggis, served with “neeps and tatties” — mashed turnips and potatoes. Buttery shortbread and whisky from the country’s more than 100 distilleries are also Scottish specialties. A stay at the elegant and historic Balmoral Hotel will enhance any visit to Edinburgh, and while you’re there, you’ll notice that Scottish actor Sean Connery was a guest, as was J. K. Rowling who finished the last Harry Potter book in one of its suites.
Weirdly enough, Central America and South America aren’t really known as top “culture” destinations, as the colonial history has mostly wiped out the indigenous history in the larger places. There are Aztec, Maya, and Inca ruins and sights, but not really enough to build a whole trip around. I’d say the most interest of those would be the Inca culture of Peru, specifically around Machu Picchu and the valley around Cusco. Alternatively, visiting Argentina is pretty much like visiting Europe from a culture standpoint. It’s quite nice there and prices are low if you know about the blue market for currency, but otherwise it may not be what you are looking for.
Let’s get started. For the November trip you are going to have a lot of competition for those flights and hotels because those are prime Thanksgiving flight dates. I would normally recommend Puerto Rico, but they won’t be ready for visitors until next year from what I hear. Just a few days ago I published a new article on which Caribbean destinations have no hurricane damage. There are a lot of great choices, including all of the busiest ones, that were untouched by the storms. You might also consider Cartagena, which is probably the cheapest option once you get there. It’s got a wonderful walled historic town area, and it’s a short bus or taxi ride to the modern area with beach hotels and such. The sand there isn’t great, but the value is very good. I wouldn’t go outside of Cartagena at the moment.
If the Caribbean sounds better, I’ll recommend Puerto Rico. The area around San Juan is fairly crowded, although not nearly as crowded as a typical resort area that is loaded with hotels. And there are many smaller resort towns on other parts of the island where people usually rent a condo for a week or two. In a town like Rincon you won’t get crowds, and you will get great beaches.
Oh, and I just noticed you asked about general safety as well. Buenos Aires is fine as long as you don’t wander into the bad neighborhoods after dark, which is pretty much true almost anywhere you go, including Europe. But Rio is sadly famous for petty crime and it’s a real issue. As long as you know what NOT to do it’s quite safe, so I’ll still recommend it as long as you read up a bit on the topic. The most common problem is when people walk down to the water on the beach after dark. As long as you know NOT to do that you should be fine, but if you did go for an evening walk near the water and out of sight of the well-lit sidewalks, the chances of getting mugged are extremely high. Again, it’s worth learning about it and it’s easy to stay safe if you do. Let me know if you have any other questions. -Roger

This is a huge question and I’d need to know more about your preferences and your budget to answer it properly. But I can give you a short version here. In my opinion, which is matched by many other people, the most interesting and dramatic cities in Europe are London, Paris, Amsterdam, Rome, and Venice. Visiting those would require about 16 days to do it properly because you’d want to spend 3 or 4 days in each city, except maybe only 2 days in Venice because it’s quite small.


I’m not really an expert on surf destinations and even less so on skate parks, although I am aware of many places that do have good surf beaches. From Ireland I think your two best bets would be either Rincon, Puerto Rico, which has the best surfing in the Caribbean and is good for longer rentals like that. You could get a reasonably priced flight into San Juan, which is also a really nice place with some surfing and great beaches, and then hire a car for the drive to Rincon.
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
Costa Rica is kind of the Thailand of Latin America in that they have great tourist infrastructure and it’s the easiest place to get around. They also have a lot to offer with the beaches on both coasts and many natural sights and activities, plus of course the Arenal volcano, which is a really nice area. San Jose is best as a place to just pass through on your way somewhere else.

Vietnam and Sri Lanka could both be excellent choices for what you have in mind. Both are best for people who already have experience in these sorts of places, which you do. Twelve days could be a perfect length of time for a classic tour of Vietnam, flying into Hanoi and spending a few days there and in Halong Bay (with a possible side trip up to Sapa), and then taking the train down to Denang for a quick transfer to Hoi An. Hoi An is really a wonderful place and 3 or 4 days there would be great. There are good beaches nearby as well. Then take the train down to Ho Chi Minh City for a few more days before flying home from there. You could also do a side trip to Nha Trang (wonderful beaches) or Dalat up in the mountains. Vietnam really is gorgeous and the food is wonderful (French influences remain) but it can be a bit complicated for new travelers because you’ll find that many people you meet are trying to hustle you a bit, particularly travel agents booking trips and tours. The hotels are generally honest and great value, and so are the restaurants. You’ll learn to ignore the annoying people quickly.


St. Bart's is a French island and a member of the European Union. First discovered by Columbus in 1493 and named after his brother Bartolomeo, St. Bart's has been populated through the years by native Arawaks, pirates, French colonists, Swedish settlers, and French citizens attracted by the island life. Owned for a time by Sweden before being returned to France, St. Bart's capital, Gustavia, was named for a Swedish king, and the language, along with French, is used for many street signs. In Gustavia, visitors interested in the island’s history can explore 17th-century forts, a lighthouse, and the small Wall House Museum. With 14 public beaches, there’s one for every taste and activity, including a swimsuit-optional spot. Boating, windsurfing, kayaking, sunbathing, shopping, people watching, and exploring the island’s shallow reefs are favorite pastimes. Last September’s Hurricane Irma caused significant damage to the island, but recovery has been swift. After closing a year for renovation, Le Barthelemy Hotel & Spa has just re-opened. Set on the Anse de Grand Cul de Sac, an ideal area for watersports, the eco-friendly hotel emphasizes wellness, with an expansive spa offering hydrotherapy, sauna, and beach yoga. This perfect December island escape is accessible by air or ferry from nearby St. Maarten.
If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.
The second option you have is food trucks – although you really have to be weary on this one. Don’t be afraid to ask them what the ingredients are, as the food is made fresh and they’re usually proud to tell you what’s in their food. Luckily, we encountered a Paleo food truck while in Portland called Cultured Caveman (pictured below) that served some keto friendly items.
Obviously you’d get a refund if an airline canceled your incoming flight, so I guess it’s more a matter of being able to book an alternative without much notice at that point, and that can be tricky. I’ll probably be coming from Hong Kong or Kuala Lumpur, and those flights are always pretty cheap. If I was coming from Europe or North America, I’d probably just wait and hope that the ash cloud starts to subside, and also get a back-up destination ready. If you mainly just want to hang out on a lovely beach and do some water activities and such, then I’d take a look at Boracay Island. However, it’s small and doesn’t come close for cultural activities or natural sights, although other parts of the Philippines are better in those regards.
I think a side trip or two will be a great idea. Singapore is a large and very interesting city, but you can see everything that you want in maybe 3 days or so. You have almost limitless options if you include the possibility of a flight. Even though Singapore itself (especially hotels) is kind of expensive, you can get cheap flights to all points of Asia from there, and the airport is awesome. Air Asia and Tiger are two great low-cost airlines with many flights out of Singapore, so you could check their destinations and find something good.
One of the best things about Puerto Vallarta is that, unlike most of the Caribbean destinations, this is a real historic town rather than a purpose-built resort community. That means that there are small and authentic (and cheap) restaurants catering primarily to locals, so you get a much more authentic experience if you prefer one. The hotel zone close to the airport is modern and posh, but you are a short taxi ride away from the lovely center of town.
Hawaii, as you probably know, would be great for what you have in mind, except that there are no cheaper options there at all. After that I agree with you that there are places in Mexico that could work. One in particular that I like a lot is the area around Playa del Carmen, which is just south of Cancun. It’s a lively and tourist-friendly town, instead of a strip of big hotels like Cancun, and there is a wide range of activities and accommodations in different price ranges.
Bali, which is just south of the equator, would be a good choice in November. It does rain a bit that month, but they are summer storms that tend to only last 30 minutes or so. It’s a wonderful island with great prices on most things, including massages. The complicated thing about Bali is that the main tourist areas of Kuta, Legian, and Seminyak are now so crowded that they can be unpleasant. I spent a month there again earlier this year, and I don’t think I’ll go back to that part of the island.
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
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.
That definitely helps! Though I think I was quite unclear in the first place. Being in the same region is definitely not a constraint. We’ve been considering Africa as well, for example! Also, a couple of days of beach time is also sort of desirable, and we’re not really into visiting cities as such. Ideally, we wish to have some time to spend on beaches/resorts/hotels along with some time in a place like a safari or something.
As for the Northern Lights, Iceland is one to consider, and its Aurora Tourism sector is pretty famous. You can get a cheap flight to Iceland from London or most other large cities in Europe, and it’ll cost about the same as a flight to Stockholm or Oslo. If you want to stay on the continent, I’d think about Sweden, even though Norway has more northern area. Both are very expensive, but Sweden is a bit cheaper and easier to get around in.
For a cheap destination in December that has great clothes shopping opportunities I can only think of two really good options. The closer of the two is Dubai. I’m not sure if you’ve been there before, but it has some of the best shopping in the world with every store imaginable and very good prices because duties and taxes are low. In spite of its reputation, Dubai can actually be visited quite cheaply if that is important. It’s famous for expensive hotels, but it’s got hundreds of more affordable hotels that can be pretty nice.
I think Spain is probably your best bet, and you can probably get there on a reasonably priced flight with a change in Dubai or Abu Dhabi. The winter weather is decent and the big cities are always packed with locals rather than so many tourists. Barcelona is probably more fun than Madrid, though both are big cities with a lot to see and notoriously good nightlife. If you get a cheap enough flight I don’t think you need to do a package. It’s pretty easy to get around Spain’s big cities just on English, as long as you do a bit of research. In 5 days you could spend 3 days in Barcelona and then 2 days in Madrid, or just 5 days in the Barcelona area. It’s a big city with plenty to see and some good day trips. You could also go to Valencia, which is also really fun and a short train ride away.
It can still be rainy in Belize in November, so it’s not an ideal time to visit. I quite like Belize and there is a lot to do there, including of course the second largest coral reef in the world. You can also head over the Guatemala border to visit Tikal and even down to Antigua for something different. You don’t get many great beaches there, but aside from that it is great.
If you ask at a hotel in India about getting train tickets, they almost certainly know a way of getting them for you. They share in the profits of the commission, so they will usually find a way. However, perhaps in Goa it is less common because the train stations are a long way from the beaches so it could be a 3-hour return trip to the station instead of a 20-minute trip in the cities.

Escape the cold weather to sunbathe on the beaches in Rio de Janeiro and ring in the New Year with a fun celebration on Copacabana Beach. And while you're near Copa, visit the neighborhood and beach that inspired the song, “The Girl from Ipanema.” Don’t overlook the other beaches, including Baixo Baby for families, Praia do Arpoador for surfers and Sao Conrado Beach if you want to leap from nearby peaks and go hang gliding.


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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.


If you're determined to travel during the holiday periods, though, book your vacation flights, hotels, and cruise far in advance. If it works with your schedule, fly on Thanksgiving Day or Christmas day; those are the least crowded days of the holiday season. And if at all possible, avoid traveling during weekends, on the days right before or after the holiday, and late in the day. It's not only crowded at airports but also northern storms can wreak havoc and create weather delays that cascade across the system.
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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