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.
Unlike most cities on South America's west coast, Buenos Aires has fairly consistent rainfall all year long, and you might see a bit of the wet stuff even during December. Still, the temperatures should be ideal for being outdoors, and this is really mostly an indoor city anyway, so when it does rain you'll be able to pop into a shop or museum or cafe and have a great time.
As Christmas approaches the city will fill up much more, so if you can go early in the month you'll be much better off. But even if you can't go before the last week of the month you'll still find Mexico City to be a tremendous bargain compared to pretty much anywhere else in North America. It's a great shopping destination, and not just for goofy souvenirs, so that's something to think about as well.
If you are looking for a cheap, beautiful, and relaxing beach destination during December then Goa is ideal. This has become hugely popular with package tourists from Europe and Israel (and more recently Russia), and the facts that pretty much everyone speaks English and there aren't many cultural opportunities means that it's a perfect place to just vegetate in a beach chair for a week or two.
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.
Spend the past two days discussing your ideas. Group thoughts; Is that adventurous and cultural enough? We want a “wow” factor. We have vacationed in Cayman Islands about a dozen weeks since the kids were little (been there done that.). We have ruled out Asia only because don’t see a huge Wow factor for the amount of travel. What about African Safari? Still not ruling out your ideas, just want to know what is Wow about Puerto Rico? Costa Rica?
Similar to so many on this list, Cape Town begins its busy season in the second half of December, so November is ideal in that the weather is nearly perfect and you don't have to worry about high-season crowds or prices. This is a city that has things available at almost any price level. Many of the hotels cater to the 4-star resort crowd, but there are also plenty of hostels and cheap hotels so backpacker-types should be able to get by on a low budget.
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This diverse and rapidly growing capital city of Texas is known for its live music scene, world class museums, beautiful outdoor spaces, pleasant weather, fine dining, and nightlife. A little bit city, a little bit country, Austin has no shortage of December activities for all. The Zach Theatre presents a rocking adaptation of the Dickens classic "A Christmas Carol" from Nov. 21 through Dec. 30, guaranteed to have you dancing in your seat. In its 56th year, Ballet Austin’s annual production of "The Nutcracker" returns to the Long Center Dec. 7-23. Holiday shoppers gather at the Blue Genie Art Bazaar to purchase unique handmade gifts including paintings, photography, jewelry, clothing, and more. Zilker Park transforms into a glittery wonderland with more than 2 million lights, 40 displays, interactive experiences, food trucks, and live music on two stages. The Armadillo Christmas Bazaar, an art and music festival, runs from mid-December through Christmas Eve with live music, two full bars, and local food specialties. Over 175 national and local artists display paintings, sculptures, woodworks, and an assortment of handmade gifts. Winter Wonderland at the Circuit is great family fun with holiday lights, a skating rink, Santa’s Village, petting zoo, carnival rides, and of course, live music. In the heart of downtown, the historic Driskill Hotel celebrates with an enormous Christmas tree and seasonal music. On Sunday, Dec. 16, Austin’s best bakers will share their holiday cookie collection, with the event’s proceeds supporting the Driskill’s traditional charity, “Cookies for Caring,” benefitting the community.
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.