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.
When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
It's actually a bit chilly in Hanoi in December, but generally very dry and exceedingly pleasant around the clock, so it's a very good time to visit. Nearly everyone who visits Hanoi will be doing it as part of a larger tour of Vietnam or other countries in Southeast Asia, and this is one of the cooler cities this time of year, therefore a nice balance to some of the places that are still quite hot.
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.
While it's true that it might be a stretch to call Cusco's November weather “great,” this is perhaps the best month of the year to visit, and the weather is quite good anyway. The high season for hotels in Cusco ends in October, yet the rainy season doesn't begin until late December, so November is that perfect combination of small crowds, low prices, and very good weather.
Those temples are all outdoor for the most part, so cooler and dryer conditions mean you can spend more time touring the temples and still being comfortable. Almost any other month of the year and you'll be better off going back to your hotel for a few hours in the afternoon, but in December you can carry on all day if you like. The town of Siem Reap is a delight in itself, but of course it fills up near Christmas.
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.
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.