My fiance and I plan to travel for a month starting Oct. 20. We’re thinking about selecting a region that would allow 4 destinations with great food, outdoor activities (hiking, swimming, horses, yoga, etc), nice accommodations that don’t break the bank, and some sight-seeing. We’re planning to get married on the trip, too. Any suggestions? Super appreciate your insight!
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.

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. 

Interestingly, December though February do get a bit cool in Cairo, so it's not a great winter break, but in November it's still pleasantly warm and bone-dry so you can enjoy the outdoors for long periods of time. If you don't mind staying in a locally-owned hotel you can save a lot of money and see some old-world charm at the same time. Reservations in advance aren't necessary, but it's best to book your first couple of days just to avoid all the confusion once you arrive.
If you are looking for a place to go abroad for a few months starting in early December, you are right on the money with Thailand as the best starting location. The weather is really nice that time of year, and it’s quite easy to keep things extremely cheap if you need to. Many of us in the travel writing community have spent months or years traveling around southeast Asia, and I’ve probably spent close to two years there myself. Bangkok is the obvious place to start and it’s an amazing city. After that you can either go north to Chiang Mai and Chiang Rai and then over to Laos, or you can head south to one or more of the islands. Cambodia has a lot to offer, and especially in Siem Reap, and Vietnam can be entertaining for all three months of your first visa there.
Another destination that might not exactly have “great” weather in December, yet deserves to be on the list, Sharm el-Sheikh is famously Egypt's most popular Red Sea beach resort. Those following the news might still hesitate to book a trip here, whether that is a rational decision or not. But at the very least this is one to consider in the future, as it's an amazing bargain once you get here.
The final month of the year marks the time when people in northern climates start looking around for an escape to the sun. Fortunately, there are big parts of the world that have their best weather of the year at this time, and are very cheap as well, once you get there. The best places to visit in December are of course close to the equator or even below it.
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.

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.
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.
What a fantastic site you have. I am in Dallas, TX and looking for a 7-10 day getaway in late November or any time in December, depending on when my passport renewal comes in. I am going solo and have a reasonable budget. My goal is relaxing mostly but as a solo upper 40’s male, it wouldn’t be bad to run into some people (and ladies) to visit with some of the time. I thought of SE Asia but travel time burns up much of the trip. Do you think all-inclusives are worth it? And any recommendations for places I won’t be overrun with families and screaming kids?
However, I also happen to be an athlete and about a month ago I reached the point where I had almost no power, no energy, constant hunger (and “hanger”) and cravings for practically anything bad like alcohol, sweets, carbs, artificial sweeteners or energy drinks. I tried to fight it. I started over multiple times. At one point I just couldn’t stick to any sensible dietary routine for longer than a day or two. Intermittent fasting, OMAD (one meal a day), TMAD (two meals a day) and keto all seemed to stop working.
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.
Venice can get pretty cold and they also have those famous Acqua Alta floods in winter, so read up on that before you go. But Rome and Munich should be easy to visit in December. One suggestion I will make is to consider visiting Rome for 3 or 4 nights and then base yourself down on Sorrento for the remaining 2 or 3 nights. Rome is one of those cities that is crowded and chaotic even in winter, to the point that just crossing the street can be frustrating, so many people get tired of that after they’ve seen the main sights. And Sorrento, on the other hand, is a lovely small city that is close to Amalfi, Pompeii, Naples, and the Isle of Capri, so it’s an ideal base to visit all of those. Sorrento is also cheaper than Rome, and a surprising number of locals speak English there, so it’s easy and pleasant. That time of year I’m not even sure if the tourist buses are running to Amalfi, although the local ones will be.
For those from the Northern hemisphere in need of decent a blast of winter sun, the picturesque coastal town of Essaouira is the perfect place to put your feet up and relax. Fresh-caught fish sizzles on beachside grills, whitewashed houses with blue shutters lend a Mediterranean vibe, and you can lose hours wandering through the dozens of art galleries and workshops.
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.

As for the alcohol thing, I’m a bit of a drinker myself, so it’s hard to offer advice to an AA person. I guess one factor could be that there are many places around the world where alcohol is so cheap and the days are so warm that many people drink during the day AND at night. If I were in your shoes, I’d probably want to avoid those places. Probably the easiest places to go would be Muslim countries and India because there is little or no drinking culture there, so they have endless evening alternatives that don’t revolve around drinking.
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.
The rainy season is over so it's an ideal time to base yourself in Chiang Mai for some outdoor activities in the area. There are temples like crazy in the city center between the old walls, but even more interesting ones in the area just around Chiang Mai. There's also great trekking and such, available quite affordably from any travel agency in the city.
As chilly temperatures arrive in the northern hemisphere, it’s spring in Buenos Aires, an ideal time to visit. The city’s jacaranda trees are decorating the streets in purple petals, hotel prices are attractive, and the weather is comfortable and dry. A cruise along the Rio de la Plata would be a good place to start, for a relaxing overview of neighborhoods, homes, markets, and the waterfront. On Sundays, get some authentic local flavor at Feria De Mataderos, about an hour from downtown, with gauchos on horses, craft vendors, musicians, tango dancers, and regional foods.
The rainy season in Cartagena winds down by early November, so this is an ideal time to come, especially toward the end of the month if you can get cheap airfare before and/or after Thanksgiving. The temperatures are pretty much the same here every day of the year, so the key is to work around the autumn rainy season to when it's dry but before hotels fill up.
Thank you for the insightful details about South America and the others! Peru, Costa rica sound ideal! Always wanted to work at a sustainable place is Costa Reecs. However, I am also quite interested to know what Brazil , rather the different parts of Brazil are like, since it is so huge would be interesting to visit during the same time of the year.. Since I love and play Capoeira too, I’m pretty tempted to visit Brazil and draw inspiration. 🙂 And what is Colombia like?
Thanks. I’ve been to other places in Egypt, but have yet to make it to Sharm el-Shiek. It’s hard to find places that are that inexpensive these days. Most of my best suggestions are in the article above. If your main priorities are beaches, sunshine, and nightlife, my favorites are Goa, India; Boracay Island, Philippines; and almost any of the Thai islands. Goa has many family-oriented beach towns, although some others are not so family oriented so you have to choose carefully there.

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.

It’s unfortunate and heartbreaking how many times I have recommended San Juan, Puerto Rico in the last few years. Once they get the power back on I’m sure it’ll be back to normal fairly soon after that, but I’m guessing probably March or later. And fortunately, Nate missed the Cancun area for the most part. Have you considered somewhere in the Cancun/Playa del Carmen/Cozumel area? I’m particularly fond of Playa del Carmen, and that flight to Cancun should be pretty reasonable for you.
If you’ve got 5 to 7 days and are starting in India I don’t think you want to fly halfway around the world, so it’s probably best to go somewhere between Dubai and Bali. Dubai has cheap flights from most places and it’s very family oriented with large play parks inside shopping malls and that sort of thing. You could get an apartment there in one of the many apartment-hotels for a reasonable price, and the December weather should be pretty good as well.
My two years in southeast Asia was over a few trips, although I did have my own apartment in Bangkok for 3 months and in Chiang Mai for another 3 months. As an American I didn’t have a national health restriction and I didn’t even have travel insurance. I don’t recommend it for everybody, but healthcare in those areas is extremely cheap and of pretty good quality. I went to a hospital once in Chiang Mai and I saw an English-speaking doctor for about US$7, and spent another US$25 or so on a prescription. My longest total trip was 3 years and 7 months (only a few years ago), and I went in and out of Southeast Asia a few times in that period.
Christmas markets sprout up all over the country this month, and from the smallest towns to the biggest cities they’re a great place to mingle with locals, learn about regional handicrafts, and sample seasonal delicacies. Depending on the venue, you can find anything from medieval reenactments to outdoor concerts. But they’re usually at their prime once darkness has set in and the fairy lights are out in full force (which means there’s also time in the day for museum visits and city touring before indulging in the market flurry). Some travelers skip dinner altogether for a smorgasbord of yuletide samplings at the wooden market huts!
I’m happy to try to help. It’s hard to say whether one 30-day trip would be better than several shorter trips. On one hand, it’s much more efficient to go for a month because it obviously saves you all the going back and forth. Also, one week is a short time to go 7 or 8 time zones away, as it takes pretty much an entire day each way, and at least a few days to adjust to the time change. Hmmm…
The secret to a pleasurable European vacation in November? Go south. While cities like London, Paris, and Berlin feel the winter chill this time of year, Lisbon has the good fortune of a subtropical Mediterranean climate—which means temperatures are in the mid 60s. Book a room at the landmark Tivoli Lisboa in the center of the city. The luxury property sits on Avenida da Liberdade, a bustling boulevard that’s akin to New York’s Fifth Avenue. Ask the hotel to arrange a “Vintage Lisbon” walking tour and explore the city’s rich art and architecture scene.
I’m in the Texas Hill Country myself at the moment (Kerrville to be exact), so we are almost neighbors. It really depends on whether you’d like a city or a beach or national parks and such. My first recommendation is Mexico City. You’ll be able to get cheap flights from Dallas, and the weather there in November is very nice and dry. Honestly, the whole huge city center is as nice as any large Texas city, and the architecture is far more interesting. You can even visit some pyramids just a bit outside of town. Before I went I assumed Mexico City would look run-down like many border towns, but it’s actually very fancy.

Uruguay is an interesting place. It seems to be a less modern and less developed version of next-door Argentina. Buenos Aires is a larger and more interesting city than Montevideo. There is a town there called Colonia, which is worth a couple days if you like old and charming cities. But most people who go to Uruguay either go to one of the posh beach resort towns (mainly Punta del Este), or they go to the tourist cattle ranches, which are surprisingly popular. If you haven’t been to Argentina yet you might find that it has more and different options, such as the Mendoza wine region and the mountain resort town of Bariloche.
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.
If you crave warmth but think the beach bores you, head to the Southwestern United States. New Age meets Old West in Santa Fe, Phoenix is still toasty and its cultural season is in full swing, and Denver makes for a great trip. And if you've never seen the Grand Canyon, winter is a good time to visit since the crowds have thinned out (but do dress warmly).
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.
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