Italy should be at least a bit warmer than England this time of year, but not by all that much in a typical year. Also, if you only have about 9 days I think I’d try for no more than 3 or perhaps 4 total cities (Venice can be appreciated in about 24 hours if you are in a hurry). And of course, Paris and Amsterdam will both be quite chilly, so I think I’d save those for another trip. My recommendation would be to spend the whole trip in Italy so you aren’t so rushed. Do Rome for at least 3 nights and Florence for 2 or 3 nights, and then Venice for 1 or 2 nights. You could still have time to pop down to Sorrento for a couple nights to see Naples and Pompeii and whatnot.
Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
I too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
Vacationing to Sicily during Italy’s traditional “off-season” has been trending in recent years, according to American Express Travel. What gives? Well, for starters there's Sicily's fabulous Mediterranean setting, as well as its rich baroque aesthetic and festive Catholic traditions. Plus, the crowds are more manageable than they are in the summer, which makes travel for families and large groups a breeze.
The most important holiday in Japan is oshogatsu (New Year), and the month leading up to it is packed with fun festivals and markets. Standouts are Shimai Kobo (December 21) and Shimai Tenjin (December 25) both of which offer great ceramics and handicraft shopping, in addition to lots of good things to eat and drink. From December 8 through the 17th, thousands of lanterns will be placed around Arashiyama, including in the enchanting bamboo forest. If you’re there on New Year’s, you’ll catch the famous the bell-ringing ceremonies -- get up real early and see the monks at Kyoto’s largest temple, Chion-in, or drop by a small-scale local shrine instead.
Oh, did you want a sunny tropical vacation that doesn’t require a passport? Done. Hurricane season is over, flights are cheap, and the water is still warm enough for swimming (and scuba diving). Almost all the tourists come here via cruise ship, which means you’re mostly not competing with them for hotel rooms -- Windward Passage, Emerald Beach, and the Bolongo are all open for business after Hurricanes Irma and Maria last year. On December 16 you can catch Jazz By The Sea down at Coral World Ocean Park, and on December 21 watch the St. Thomas Lighted Boat Parade, where contestants (boats) are judged on lights, originality, and holiday cheer.
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.
You could go somewhere that’s cute in December, or you could go somewhere that’s iconic. If you choose the latter, here’s absolutely everything you need to know about traveling to Yellowstone. In brief: There are tons of winter activities (snowmobiling, skiing, etc.), and even though most of the roads will be closed, there’s oversnow transport to get you around the park. Look for wolves at dawn and dusk, watch frost-covered bison plowing through the deep snow, and see the steam rise off Mammoth Hot Springs. If you’re a backcountry camper who knows what they’re doing, permits in wintertime are free.
It's actually a bit chilly in Hanoi in December, but generally very dry and exceedingly pleasant around the clock, so it's a very good time to visit. Nearly everyone who visits Hanoi will be doing it as part of a larger tour of Vietnam or other countries in Southeast Asia, and this is one of the cooler cities this time of year, therefore a nice balance to some of the places that are still quite hot.
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.
Unfortunately I’ve only been to Cartagena in Colombia, although I know of some travel bloggers who live in Medellin and love it there. The mild weather year round is one reason people love it. I don’t speak much Spanish, which is a problem in much of Latin America, but evidently there is a pretty big scene of various expats and English speakers, so Spanish isn’t so critical. In other words, I like the sound of your idea and I imagine it’ll be great, but I haven’t been there yet so I am really not qualified to give real advice. Best of luck with whatever you choose. -Roger
Thank you for the kind words. Interestingly, had you not included that you’ve been to Costa Rica, I’d say that was the obvious suggestion because they really do that sort of thing well and it’s at least a bit better organized than its neighbors. And if you were less concerned over travel time, I’d have some interesting suggestions for you in Asia. However, as you know, it takes nearly a full day just to get to Asia from the US or Canada, and then a few days to adjust, so you might be best off saving that for later.
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.