Unlike Bangkok, which has warm evenings and blazing hot days pretty much all year, Chiang Mai cools off nicely during December, at least in th evenings. This is an outdoor city with an emphasis on hiking and exploring temples so the cooler temperatures will be welcome for most people. It's still hot most days, and quite dry as well, so it balances nicely.

The Brazilian currency has been falling in recent years, and if this trend continues then Rio de Janeiro will be squarely back into the bargain category. It's certainly not as cheap as it used to be, but for the amazing beaches and scenery it's easily worth it as long as you plan well and stay safe. In fact, Rio has some of the best beaches in November anywhere in the world, and a vibrant city right next to them.
The same resort that charges US$300 per night in January will usually go for US$200 per night in November, especially earlier in the month. And this goes for all-inclusive resorts as well, which start at US$116 per night for two people in the low season when we last looked. If your main goal is relaxation in a perfect climate, Punta Cana is probably the best value in the entire hemisphere. And if you are wondering where to go in November for a beach all-inclusive then this is your best choice.
Regarding Thailand, I’m not familiar with any islands that are beautiful and not touristy. Phuket has beaches all over the island and many of them are isolated so the only guests are those staying at the resort in front of them. If you search other travel sites, including travelfish.org, which I think is the best site for southeast Asia and it’s run by a friend of mine, you can find more information about more obscure Thai islands. One challenge could be that you might have to take two or three total flights and then a ferry ride to reach them.
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.

I think the best place for what you want is Thailand. You can choose from Phuket or Ko Samui or one of many other islands, and they all have nice beaches and good nightlife at a very reasonable price. There are other places in Asia that have warm December weather, but Thailand’s tourist infrastructure is better than the others so it’s just much easier to get around and do what you want. Let me know if you have any other questions. -Roger
At the Kimpton Rowan Hotel, admire the appealing outdoor art while you have a quick bite at Juniper Table or head to the roof for dinner at the 4 Saints with its menu of seasonal Mediterranean-style dishes. From the restaurant and rooftop High Bar, you’ll feel as if you can reach out and touch the San Jacinto Mountains. The Palm Springs Art Museum, Indian Canyons, golf, casinos, luxurious spas, and the Palm Springs Aerial Tramway to the mountain top are just a few of the many things to do. Visitors can fly into Palm Springs International Airport or drive about three hours from Los Angeles.
Plus, Colorado is home to the world-renowned Breckinridge, a historic town at the base of the Rocky Mountains’ Tenmile Range that’s well-known for its ski resort, year-round alpine activities, and Gold Rush history. You’ll also find tons of shops, galleries, and restaurants housed inside colorfully-painted Victorian buildings, along with four whole mountain peaks that provide 2,358 acres of enough variety to suit even the most seasoned of skiers, boarders, or even snow-shoers. It’s also important to mention that last season, the Summit County municipality saw 447 inches of snow. Lifts open up in November, so what are you waiting for?!
November is a perfect time to visit Bermuda, with temperatures in the mid-70s and pink sand beaches that are less crowded than in high season. There are many ways to explore the 21-square-mile island, from under the sea where you can snorkel or dive among coral reefs or shipwrecks to the Bermuda Railway Trail, an 18-mile abandoned rail bed that winds through scenic landscapes and shorelines. The Crystal Caves take you into an underground world with a subterranean lake and white limestone stalagmites. The 36-acre Botanical Gardens, established in 1898, inspired John Lennon during a two-month Bermuda stay that led to his Double Fantasy album.
November brings the annual Vodafone Mexefest Music Festival (Nov. 24-25), a gathering of popular artists in venues throughout Lisbon. The Lisbon & Sintra Film Festival, in its 12th year, is a celebration of cinema with directors, actors, artists, musicians, and writers in town for the event (Nov. 16-25). Billed as the “largest technology conference in the world,” Web Summit began in 2010 as a way to connect industry and the technology community (Nov. 5-8). The year’s new wine and the ripening of chestnuts are celebrated with the Magusto, on Nov. 11, St. Martin’s Day. The holiday spirit becomes apparent at the end of the month, with colorful lights and roasted chestnut vendors along the streets. 
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