Costa Rica, as you probably know, is all about nature and adventure sports, along with some decent beaches. It would be perfect if you are up for that sort of thing. If not, Santiago and Valparaiso (nearby cities in Chile) could be good for more of an urban adventure. Or Buenos Aires is even nicer and more interesting (and probably cheaper if you bring cash) if you can get a deal on a flight there.

Bali, which is just south of the equator, would be a good choice in November. It does rain a bit that month, but they are summer storms that tend to only last 30 minutes or so. It’s a wonderful island with great prices on most things, including massages. The complicated thing about Bali is that the main tourist areas of Kuta, Legian, and Seminyak are now so crowded that they can be unpleasant. I spent a month there again earlier this year, and I don’t think I’ll go back to that part of the island. 

My recommendations depend on your starting location so for now I’ll just assume you are starting somewhere in the USA. If you are looking for a really nice beach AND really good night life your best choices are the Cancun area, Puerto Vallarta, and San Juan, Puerto Rico. If you are in the eastern US or Canada it’s probably faster and cheaper to go to Cancun and if you are in the west Puerto Vallarta is better. San Juan will be more expensive because there just aren’t many cheap hotels in the good parts of the city. For the Cancun area I would recommend Playa del Carmen (about an hour south of Cancun Airport) because there are fairly cheap hotels near the town center, which is packed with bars and restaurants. In Cancun itself the best nightlife is in the heart of the hotel zone, and all of the hotels there are pretty expensive. Let me know if you have any other questions. -Roger
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
As for Indonesia vs. Philippines, I’ve been to Bali quite a few times but I haven’t been to Bandung. And for the Philippines I’ve spent time in Manila and in Tagaytay just to its south, and I don’t think I’d recommend those for a longer trip. And I also spent two weeks on Boracay Island, which is quite nice, but it’s small and also a place I wouldn’t recommend for a longer trip like yours. For information on Indonesia you might go to my friend’s site – travelfish.org – which is an excellent resource. Unfortunately, they don’t cover the Philippines yet. Best of luck with what you end up doing. -Roger
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.

If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger
From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
On the hunt for a non-traditional ski vacation? Look no further than the Japanese Alps. According to American Express Travel, the region has seen an increase in bookings during the holidays in recent years. And while December has historically been less popular than Japan’s peak season—April-November—adventurous travelers are now intrigued by the wilderness of Japan in the winter. The Hida, Kiso, and Akaishi alps are home to indigenous snow monkeys, volcanoes, and lava plateaus, plus, visitors are drawn to the area for its pristine ski offerings, natural hot springs, and rural hiking.
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger 
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