If a warm weather getaway sounds appealing, consider seeking the sun in Cartagena where summer is approaching. The South American city offers history, Christmas spirit, and unique gifts for holiday shopping. Sun-drenched Phuket, Thailand’s popular island, is a place to relax during the day and party at night. St. Bart's in the Caribbean is recovering nicely from hurricane damage, an ideal spot for a winter vacation. Miami’s December weather is perfect for a warm Christmas, and Art Basel, early in the month, is an exciting time for fans of contemporary art. In Santa Barbara, a few days of pampering might fit the bill, or you can join in their holiday festivities throughout the month. Death Valley, in the middle of the Mojave Desert, offers a respite from the crowds and a chance to enjoy quiet days and starry nights.
Hotel prices remain low through all of November for the most part, so you'll have a good shot at deals at 3-star and above beach resorts that are trying to fill rooms during the slow season. Even if you are paying near the high season rates the hotels and everything else are bargains here compared to almost anywhere else. Cartagena is one of the cheapest places to travel in November on a beach, and you'll get less rain as the month goes on.
I’m in the Texas Hill Country myself at the moment (Kerrville to be exact), so we are almost neighbors. It really depends on whether you’d like a city or a beach or national parks and such. My first recommendation is Mexico City. You’ll be able to get cheap flights from Dallas, and the weather there in November is very nice and dry. Honestly, the whole huge city center is as nice as any large Texas city, and the architecture is far more interesting. You can even visit some pyramids just a bit outside of town. Before I went I assumed Mexico City would look run-down like many border towns, but it’s actually very fancy.
If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.

Thank you for the kind words. I know what you mean about the image of Thailand and Bali, particularly among Australians. On one hand you could go to either of those places and easily avoid the most notorious party neighborhoods, but it’s probably easier to head somewhere else since both of those places are so crowded that time of year anyway. I do have a few suggestions, which I’ll describe briefly and then if you want more details about any that appeal to you I can do that in a follow up comment.
If you are looking for an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.
Blisteringly hot in summer, Tokyo is a breeze in the cooler months. Fight the dizzying jet lag and head out for the world's best sushi or ramen, shop in the city's amazing department stores, and visit the parks surrounding the Imperial Palace in the center of the city. Escape the crowds somewhat by heading to Yanaka Ginza, which retains a bit of old Tokyo and has plenty of places to eat and shop. Do make time for a side trip to Hakone, where you can visit a Shinto shrine and see magnificent Mount Fuji on a clear day.
Another option is Chiang Mai, Thailand, which has wonderful weather in December as long as you don’t require constant heat. It is popular with tourists and expats, but it’s not an overly touristy city so it never seems too crowded. Other options in that general area to consider are Luang Prabang, Laos, and Siem Reap, Cambodia. Let me know if any of these sound interesting and I can provide more info if you need it. -Roger
The December weather is pretty much perfect and dry, and airfares and hotel rates are very reasonable up until Christmas itself. If you are in California you might also consider Los Cabos, although Puerto Vallarta is more interesting and usually cheaper as well. This is definitely one of the best places to go in December if you are anywhere near the Pacific Ocean.
December is a popular month to go cruising around Hawaii and Mexico. It’s an ideal family trip, especially with most kids in the US out of school for the holidays. Experience the Hawaii’s tropical paradise. Pick a popular cruise liner and visit ports of call like Nawiliwili on Kauai, Honolulu on Oahu and Kona on the Big Island. If the Caribbean floats your boat, we recommend taking a cruise to explore Mexico’s Costa Maya, Cozumel, Ensenada, Acapulco, Cabo San Lucas, Puerto Vallarta and more.

Once again, it's worth noting that the first half of December will be cheaper and far less crowded than the time around Christmas, so if it's possible you should come early for best value. Still, compared to, say, Miami Beach, Cancun and the other Mexican resort towns are far cheaper and at least as fun as well. By the way, Cancun is mainly just a strip of high-rise hotels along a lovely beach, while Playa del Carmen (about an hour south) is a real tourist-friendly town with smaller hotels as well as hundreds of restaurants and shops to choose from.


Hurricane season officially ends on November 30, so it's safe to visit the Caribbean. There's good news for skiers, too, since most of the northern hemisphere is heading toward winter as the year comes to a close and mountain regions become dusted with snow. Couples who prefer a warm-weather vacation in November or December will have to travel south to find balmier temperatures — and prices begin their uphill climb toward the high season.

As for the alcohol thing, I’m a bit of a drinker myself, so it’s hard to offer advice to an AA person. I guess one factor could be that there are many places around the world where alcohol is so cheap and the days are so warm that many people drink during the day AND at night. If I were in your shoes, I’d probably want to avoid those places. Probably the easiest places to go would be Muslim countries and India because there is little or no drinking culture there, so they have endless evening alternatives that don’t revolve around drinking.
Hurricane season officially ends on November 30, so it's safe to visit the Caribbean. There's good news for skiers, too, since most of the northern hemisphere is heading toward winter as the year comes to a close and mountain regions become dusted with snow. Couples who prefer a warm-weather vacation in November or December will have to travel south to find balmier temperatures — and prices begin their uphill climb toward the high season.
The December weather is actually warm enough to sit on the beach, but most people who come to Dubai tend to just relax and do a lot of shopping at one of the enormous and modern malls here. The restaurant scene is very interesting as well, and you can eat cheaply if you follow the local workers, or go to one of the hotel restaurants and get world-class cuisine.
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.
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central. 
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