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.
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.

Much of Mexico is ideal in December, after the rainy season has ended; if you go early in the month, you’ll avoid the peak holiday-season rates that kick in around December 18. On the Pacific coast, the landscapes are still ultra-tropical green, and the ocean is bathtub-warm (80s), with exceptional clarity for scuba diving and snorkeling. Mexico City is a smart place to spend the holidays, when the locals have headed to the beach and you’ll find much less traffic in this famously congested city. (Do keep in mind, though, that some of the more sought-after restaurants and galleries will be closed.)
Portugal does have one of Europe’s best autumn climates, but as you’ve noticed November can be a bit rainy. That said, in my experience it rarely rains for long periods in that part of Europe so I think it’s very unlikely that a big part of your trip would be “rained out.” Also those cities have lots of great indoor attractions so if you see that it’s supposed to be clear in the morning and drizzly in the afternoon, you can plan to explore neighborhoods in the morning and plan to visit a museum or castle in the afternoon. It’s a bit of a crap-shoot and generally Portugal has nicer weather than most of the rest of Europe at any given time. I hope this helps. -Roger
This looks great and I wish I could be of more help. As I mentioned before, my first safari will probably be in 2017. I have a couple safari articles on this site from writers who have done them, and I’ve read a lot about the experience and the extremely positive reviews that most of them get. But having not yet done one, I wouldn’t feel comfortable offering specific advice. There are hundreds of articles on the internet that discuss these safaris, so I recommend you seek advice from someone with plenty of first-hand experience. Just be careful not to rely too heavily on a commercial safari outfitter, and try to seek advice from a travel blogger or other regular consumer. Have a great trip. -Roger
New Zealand wines are world famous, and wine tours are popular with visitors. Auckland, New Zealand’s largest city, is set on the waterfront, with beaches, parks, and cruises to the nearby islands. The capital city of Wellington on the southern tip of North Island is home to New Zealand’s national museum, a great place to learn about the country’s cultural history. Christchurch and Queenstown are located on the South Island. There's so much to do in New Zealand — and it's convenient to reach on Air New Zealand’s nonstop flights from Los Angeles, San Francisco, Houston, and Honolulu, with a nonstop from Chicago to Auckland beginning Nov. 30.
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.
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.
Hey Roger. My girlfriend and I are planning to go during Christmas for 13 days from San Diego, CA to South America mainly on the west side. We are not up for beaches but rather historical, adventurous, and scenic places. We are keen on Cusco (Peru) (Inca Trail), Quito (Ecuador), Costa Rica (Rain Forest), Bogota (Columbia). Please can you help us with your expert advice on which cities are a must for first timers to South America. We are not picky and simply want to have a fun time. Thank you for your time.

If you are looking for beach weather in December then most of your list won’t work, and several of them are only on rivers. Starting from Kolkata you have many good choices that are much closer to you than anywhere in Europe or the Canary Islands, or the Caribbean for that matter. In fact, I’m a bit confused by your list because there are so many different types of places on it, many that aren’t warm or on beaches.
If this were last year I might have also suggested San Juan, Puerto Rico or Cartagena, but both of those have issues at the moment. If for some reason you don’t like what you see in Costa Rica, there are also some really nice resorts in Panama, especially in the San Blas Islands area. Aside from those you’d probably have to fly longer than you prefer. I hope this helps. -Roger
Early December is the end of the rainy season in those areas. The storms tend to be short by that time, but still you will probably get a few quick downpours a week. I’m not an expert on getting around in the Philippines, though I do know that it’s rarely fast or easy. If you want a place to relax then Boracay Island might be the best. Sorry I couldn’t be of more help. -Roger
Later in the month, the day after Thanksgiving begins Christmas season with the Ford Holiday River Parade and Lighting Ceremony. Decorated floats wind through the illuminated trees and bridges along the river. Luminaria, San Antonio’s annual free contemporary arts festival (Nov. 10-11) will take place in Hemisfair and other downtown venues, unveiling a special program at the Mission San Jose, a UNESCO World Heritage Site. San Antonio has been recognized as a Creative City of Gastronomy by UNESCO’s Creative Cities Network. Influences of Mexican, Spanish, German, French, and Native American cuisine and ingredients combine to form the city’s culinary heritage, increasingly attracting foodies to its hundreds of unique restaurants.
This creamy-yet-virtuous gratin of greens from Ivy Manning is crowned with crunchy homemade bread crumbs tossed with nutty-tasting brown butter. Make ahead: The gratin can be assembled up to one day in advance. Allow the gratin to cool completely before covering it with plastic and storing it in the refrigerator. Add 10 additional minutes to the baking time.
December is a fun time to be in Rajasthan (though a busy one—this is peak season). The weather is cooler—something to relish, as it means long explorations into the bazaars, wonderful walks around the forts, and a chance to explore the villages on foot without overheating. Evenings are spent wrapped in beautifully decorated Rajasthani shawls and blankets as you dine outside by firelight. The winter light is beautiful, particularly in the villages, making this an ideal time for any travelers with a passion for photography.
Obviously you’d get a refund if an airline canceled your incoming flight, so I guess it’s more a matter of being able to book an alternative without much notice at that point, and that can be tricky. I’ll probably be coming from Hong Kong or Kuala Lumpur, and those flights are always pretty cheap. If I was coming from Europe or North America, I’d probably just wait and hope that the ash cloud starts to subside, and also get a back-up destination ready. If you mainly just want to hang out on a lovely beach and do some water activities and such, then I’d take a look at Boracay Island. However, it’s small and doesn’t come close for cultural activities or natural sights, although other parts of the Philippines are better in those regards.
Resolve – My number one asset to staying on track was my resolve. I made my mind up before we left that I would not give in when tempted and that I would be entirely aloof for donuts, desserts, fries, and other favorite treats. I just kept reminding myself that I could enjoy those foods again perhaps on our next weekend getaway or at the end of our vacation if I chose to have a cheat day. Otherwise, they would be dead to me because I didn’t want my kids feeling guilty eating treats in front of me. I don’t want them ever to relate being good or bad based on what they ate so again; I had to have the mindset that it wasn’t a big deal.
That was very nice of you to take the time to mention this. Interestingly, I’ve been to Bali exactly twice so far (going again in early 2016) and both times have been in December. As you have probably noticed, the rainy season in Bali can be VERY rainy at times, which is why I didn’t put it on the list during the worst months. I still clearly remember standing in almost 2 feet of water trying to push the minibus I was riding in to a dry enough area to start the engine again. That was on the way to Ubud, but most of the time the rain isn’t problematic and I’d go back again again in December if given the chance. Just don’t expect any Christmas decorations or celebrations because they pretty much ignore it there, even in tourist areas. Have a great trip. -Roger
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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