From England I would say your cheapest and best late December destination with warm weather and reasonable prices is going to be Phuket. There are some other Thai islands that might be a bit cheaper, but they would be more complicated to reach, and they’d have fewer activities for the boys. Here are some Phuket resorts good for families. You can see that the price range is wide from cheapest to most expensive. In late December it’s peak season so you’ll pay at or near the top of those ranges.
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.
There are always those travelers who celebrate the end of summer and the opportunity to don a sweater and take out the wool scarves and quilted jackets. For them, Iceland would be a perfect destination, with a chance to see the Northern Lights and adorable sled dogs. Montreal is another place with a winter chill, and at the end of the month, you might even find an early Christmas market. San Antonio gets into the holiday spirit at the end of November as well. Sedona offers chilly nights and gorgeous scenery, while Hilton Head Island still enjoys autumn weather and activities.
The rainy season is still finishing during November in Central America, but a bit north and south of that it's dry enough to make visiting very worthwhile. Better yet, it's still low season for hotels in most places even though the weather has gotten nice. Latin America is filled with excellent bargain choices and it has some of the best places to visit in November.
Fortunately, it rarely rains at all in Cairo, so even though December is one of the wetter months, that means nothing and you are unlikely to see even a drop of rain. Hotel prices do reach their peak in Cairo starting late in December, so it's best to go early in the month if possible. Egypt is definitely one of the cheapest places to travel in December, and the weather is surprisingly nice as well.
Thank you, and I’m always happy to hear that people find this useful. Buenos Aires is a wonderful city and it feels very modern and very European, at least compared with most of the rest of South America. I would think that bringing a baby there would be similar to bringing one to, say, London or Paris. Rio de Janeiro is perhaps the most beautiful city location on earth, and it’s got some very rich areas (mostly along the beaches) and many dodgy areas. They also seem to struggle more with infrastructure there so bus service isn’t very modern and that sort of thing. That said, I haven’t been since they hosted the World Cup and Olympics and I’ve read that much of the situation has improved. Long story short, I think you might just have to be a bit more careful in Rio when choosing a hotel and neighborhood and that sort of thing, but generally I think you’d be good.
For the record, the official Hurricane Season runs from June 1 to November 30, but hurricanes in November are extremely rare, so we have likely seen the last of them for this season. The devastated islands will need help rebuilding, and the remaining islands are hoping that visitors know they need the business as well, and that there is no risk of big storms starting in December and usually earlier. -Roger
For those looking for an even calmer slice of paradise without all the holiday festivities, try Waimei on Kauai’s southwestern shore, which offers calm waters and sandy beaches that are especially attractive in the early winter months. Get away from all the gloomy weather of the East Coast by trying out a Waimea vacation rental—it’ll definitely make for makes the perfect base to explore all Kauai has to offer.
All of my best suggestions are in the article above, but I’ll try to expand a bit more. The tricky thing, as you probably know, is that November is part of the heavy rain season in most of Thailand and the other popular southeast Asian countries. There are wet months in summer with just short rain storms, but in November it can often be rainy all day.
One thing I can assure you of is that those countries are very modern and well organized, and they know how to deal with winters well. So you really don’t have to worry about getting stuck or things being cancelled. As for getting around, the trains are modern, and they can be reasonably priced if you buy a couple months in advance. Otherwise, flying is probably your best bet because it’s a large area and you’ll probably want to go well to the north, and the trains might take many hours. You could even rent a car, which could be good if there is more than one or two of you. Have a great trip. -Roger
Actually, most of the popular European cities have fairly mild winters, in that they don’t spend much time below freezing and snowstorms are rare as well. It’s hard to make suggestions without knowing about your tastes, but I will tell you that the most popular European cities are London, Paris, and Rome, and none of them get snowed in often. If you are going to Italy, you should also go to Florence and maybe Venice as well.
As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.
Even if you can't sunbathe, the weather is still reliably pleasant all the time, with almost no rain. Weekly and monthly apartment rentals here are very popular, but there are plenty of hotels and hundreds of restaurants for those coming for shorter periods. If you want to be with the most English speakers you'll want to focus on the southwest area of the island around Los Cristianos and Playa de la America.

Eat Breakfast In – I know this isn’t always possible, and it’s certainly not a deal breaker, but we ate breakfast in most mornings. This started my day off on the right foot, and I could make my eggs exactly how I like them. I didn’t get tired of eating bacon and eggs all week, but if you do there are so many keto breakfast options if you’d prefer a variety of foods. For me, this was budget friendly, and I didn’t have to buy a ton of extra groceries. Also, I have a big family with two of my four kids being 3 and under. It takes us forever to get out, so cooking breakfast is an easier option for us. If you’d rather eat out, I get it! Keep scrolling for other helpful tips.
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.
Another option would be Cambodia and/or Vietnam. The town of Siem Reap, which is just next to the Angkor Wat Temples is the real highlight. Phnom Penh is worth a quick look, but not on a shorter trip. Vietnam itself is a wonderful and gorgeous country, and you can see a lot of the highlights in 10 days or so. It’s also very cheap, even around Christmas. You could fly into Hanoi and then go see Ha Long Bay, and then take a train down to Hoi An. After that you could go to Nha Trang for the best beach experience or the hilltown of Sapa. The city of Ho Chi Minh City is quite crowded and you might not like it for more than a day or two.
Based on your description, you definitely want to go to Costa Rica. The neighboring countries have many similarities, but Costa Rica is the shining star in Central America for tourism. They have endless national parks and nature sights, but also lovely beaches and adventure activities. The area in the north around the town of Tamarindo is the more luxurious part of the country, but there are many other beach towns on both coasts that could work for you. You will also probably want to spend one or more days in the Arenal volcano area, which has many other great activities. The Caribbean coast is more laid back and less family oriented, so better to focus on the Pacific. Have a great trip. -Roger
If you have a flexible schedule, or if you just happen to have some time off in November, you are in luck. This is honestly the best month of the year for finding cheap destinations that also have fantastic weather. Since most people don't start their winter travel until mid or late December, it means crowds are small and hotel prices are low through huge sections of the travel world. Those wondering where to go on holiday in November have many great choices at bargain prices, although airfare may cost a bit.
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!

Early in your message you say the last week of November, and then later you mention “late December,” so I’m not sure which it is. But if it’s late November, I think Italy could be a great option, as the weather there is still quite nice, at least in the south. You could go to Venice for a day or two and then Florence and Rome, and then maybe spend 5 or so days in Sorrento. I spent 5 days in Sorrento in mid November two years ago and the weather was very nice, even if it wasn’t warm enough to sit on the beach.
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.
As for alternatives, the most obvious are the various islands of Thailand, with Phuket being the largest. It’s peak season in December in Thailand, but still pretty affordable by most standards. I spent a month in Phuket the following December, interestingly enough, and I prefer Bali even though it’s hotter and more humid. Hopefully this helps and let me know if you have other questions. Helping people figure out where to go is something I really enjoy. -Roger
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.
I totally agree about the solo traveling thing being down to luck in many cases. Right now I’m on a long trip around Europe again, and from one night to the next I might meet a bunch of interesting people, or be sitting there alone in a sea of locals with no interest in chatting with foreigners. At least in a place like Goa, everybody is on holiday, so I’ve had good luck meeting people.
I am wanting to plan a college graduation trip for 10 days/2 weeks during the last days of December and early January. We live in Az. The graduate would like to do the Galapagos or Austraila or New Zealand. I am thinking it is too late to plan the Galapagos as those trips seem to get booked so far in advance. We want to have a memorable trip. Are these destinations you would suggest? Any other suggestions? We want to be somewhat active, not just driving and looking at sights.

I know Italy is the world’s top wine producer and they obviously make a lot of olive oil as well. I’ve seen on many travel shows how it’s fairly easy to visit the olive oil places, and of course most wineries have places where you can see the process and taste it. The thing is though, that even Sicily is quite chilly in December so they might close down for the season. You definitely won’t get sunbathing weather in December at all. I would say you are best off in May, June, September, and October to get good weather and not have to deal with the insane crowds in July or August. Tuscany is the easiest to reach of the 3, but because of that its beach towns are most likely to be crowded in those warm months. I hope this helps and let me know if you have any other questions. -Roger
Those who adore the holidays and don’t mind the cold (the average high is around 48 degrees) might consider an end-of-year trip across the pond. Arguably Europe’s most festive destination, December in London promises charming Christmas markets, show-stopping Christmas trees, and streets covered in twinkling lights. A number of posh hotels, like 45 Park Lane and The Dorchester even have Christmas-centric packages available to get you into the holiday spirit.

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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