It's been said Jackson Hole is where Aspen meets Palm Springs. Ski season, however, really starts in mid-December. There's world-class—not to mention some of the most vertiginous—skiing in the continental U.S. Plus, miles and miles of trails and nature to enjoy less vertically trekking through Grand Teton National Park and Yellowstone National Park. To put much of this at your fingertips, the Four Seasons Jackson Hole has a ski concierge and is a ski-in/ski-out property.
Hi Roger, What a great list! Answers to this question may not involve “great” weather. My 40+ yo boyfriend has never been outside the US (!) while I’ve traveled a bit (France, Spain, Italy, Greece, Iceland, Lebanon, E/W Canada, Mexico) and he’d rather go somewhere we both haven’t. We’re in Richmond VA and we’ll be travelling 11/22 – 26 this year. We love being outdoors and solo adventuring, don’t mind putting on rain jackets and lightly hiking/biking around old sites in 50-80 degree F weather; we enjoy delicious cuisine in hole-in-the-wall restaurants and staying in quirky hostels/Airbnb but also spending at least one day being tourons on a big red bus if available. Any ideas in eastern/western Europe? He’s really looking forward to going there. Thanks!
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.
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.
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.