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.
If you are looking for first-rate destinations that are among the cheaper European cities, I’ll suggest Prague, Budapest, Krakow, and Berlin. You could visit all four of them by taking trains, or choose any one, two, or three. In December you can get quite a nice room in any of those cities, with Berlin being the most expensive by a bit. Food and attractions are also quite affordable in those cities.
Those wanting to hike to Machu Picchu will also find this to be an ideal month, since getting in a group will be easy even without much advance notice. The train to Machu Picchu is expensive year round, and reservations should be easier to get the day before this time of the year. Hotels are always cheap in Cusco so you can afford to get something nicer than you are used to this month.
You’ve been to Cancun, but have you been to Playa del Carmen? Personally I much prefer it because PdC is a lovely tourist town with hundreds of little hotels and restaurants and bars, unlike Cancun, which is mainly a long string of high-rise beach hotels that are so spread out that you are nearly trapped in your own hotel. It’s about an hour south of Cancun airport by taxi or shuttle. That would be another of your cheaper options, partly because flights into Cancun are pretty cheap. It will be the tail-end of the rainy season in all of these places, but that usually just means a 30-minute rain storm a few afternoons each week.
If you are open to Africa you should consider Morocco. It will be a bit chilly in December, but still warm enough to enjoy everything. The culture there is fascinating and it’s also very tourist-friendly and safe. I think it would be cheaper for you to fly to Morocco than to the Americas, and the daily costs are very reasonable as well. Those should give you some things to think about, and feel free to follow up if you have other questions.
Always happy to hear that people find this useful. If you are looking for a driving holiday with warm weather in December I think you’ve already narrowed down the best choices. New Zealand will be ideal, although maybe not for more than two weeks or so. As you might know, the South Island is more scenic than the North, but the North has many great things to see and do as well.
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.
Aside from that, this is a bit tricky because you obviously want to avoid longer flights for a short trip and especially with an infant. And some of the closer options are not close to a major airport, so they are still hard to reach in half a day or so. I think if you want to go farther than Goa, it’s probably best to look for other options in Thailand. As you know from previous visits, Thailand really has tourism figured out and it feels safe and well organized there. Cambodia and Vietnam also have beaches, but none that I’d recommend for a short trip. It’s the same with the Philippines, and the flights start getting longer. Phuket is the largest Thai island by far and it’s got over a dozen different beach areas and towns to choose from. Patong Beach is the main beach town and I wouldn’t recommend it for a family, but Kata and Karon beaches are just south of that, and they are nicely family oriented. Phuket also has a large airport, so getting there quickly is pretty easy compared to other beaches and islands in the area. Phuket’s beaches are also very nice. I wish I had more suggestions for you. Let me know if you have any other questions. -Roger
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.
Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.
Vietnam might fit the bill for what you are looking for. The most popular itineraries are to start in Hanoi and end up in Ho Chi Minh City, or the other way around. There is a nice train connecting them that is scenic in many places, and the best must-stop place in between them is Hoi An. You also don’t want to miss Halong Bay, which is just outside Hanoi. Vietnam mostly attracts cultural travelers rather than party people. The food is excellent (France used to run the place) and there is plenty of culture all around, in addition to some nice beaches in Nha Trang and Da Nang (next to Hoi An).
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.
Orlando’s theme parks are a major draw for families (and big kids, too!), but this iconic experience doesn’t necessarily come cheap. During the pre-Christmas November lull, however, hotels often offer attractive discounted rates, meaning potential savings and – more importantly for the kids – less time spent standing in line. Those looking for a more alternative American adventure should consider the island of Puerto Rico in November. While there’s a chance of rain (but a greater chance of balmy beach-lounging days), the out-of-season discounts are as appetising as the island’s take on Thanksgiving dinner: turkey stuffed with mashed plantain.