As for alternatives, the most obvious are the various islands of Thailand, with Phuket being the largest. It’s peak season in December in Thailand, but still pretty affordable by most standards. I spent a month in Phuket the following December, interestingly enough, and I prefer Bali even though it’s hotter and more humid. Hopefully this helps and let me know if you have other questions. Helping people figure out where to go is something I really enjoy. -Roger
This year I’ve based myself in Miami, USA, primarily so I can visit many places in the Caribbean that I hadn’t been to before. I just got back from a week in Jamaica and soon I’m going to Puerto Rico, Dominican Republic, Panama, and Colombia, as mentioned. But in December I’m hitting the road again and I’ll be in Asia for the winter and probably in London for much of 2016. Sorry I don’t have more specific information to help you plan your trip, but it sounds like you’ve got some really good choices already under consideration. And I’m sure you’ll have a great time. -Roger
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.

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.


The Canary Islands are always an option and the weather in November is pretty decent. I spent almost a month on Tenerife a couple years ago and I thought the nightlife was mostly pretty cheesy, although at least the drinks are cheap. I think in summer the nightlife there might be good, but in the other months I think it’s pretty quiet because it’s mostly older visitors from northern Europe.
December is the end of the rainy season in Boracay, but by the middle of December you would probably only get a few quick tropical showers a week. Room rates are a bit lower at that time as well, so it can be a great time to visit. If you were looking for a place to go for 2 or 3 days, I wouldn’t recommend it because it does take some time to get there and you could be a bit unlucky with the rain. But if you are going for longer than that I’d highly recommend it. It’s a wonderful little island that feels like you’ve gone back in time to before mass-market tourism in places like Phuket.
If I were you I’d fly to Bangkok and stay at least 2 or 3 nights in the famous Khosan Road area, which has a bad reputation with some people, but it’s really fun. It’s also cheap, and a short walk from most of the main cultural sights. After that you could fly to Ko Samui or Ko Phagnan or Ko Phi Phi, and easily find the better party spots. You could also go to Phuket, but I prefer the others for younger people. Phuket has loads of nice beaches for families and couples, but the one “party town” (Patong Beach) is a bit over the top, and mostly geared for groups of men who want to go to the “beer bars” and strip clubs and whatnot. The smaller islands will have a more mixed crowd, including many backpacking females. Hopefully this helps. Let me know if you have any other questions. -Roger
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.
I have been reading the thread with great interest. I took my 2 daughters aged 11 and 18 to SE Asia in December and they loved it. Siem Reap – lovely vibe over new year and not too busy. Would stay longer than 3 days because the heat and humidity slows you down and you would rather want to cool down in the hotel pool in afternoons and try and squeeze in more than 1 wat in a day. Easy to get around and good food and vibe in Pub Street.
November can be an ideal month to visit Boracay Island, even though you'll probably see a few quick rainstorms each week. This stunning and laid-back island is in the Tropics, so you can get a quick cloudburst a few times a week this time of year, but they are easy to avoid and the sunsets that form as the clouds are leaving again are often so gorgeous that it's all worth it.
Last month we had a week long vacation to Sardinia. You can watch the vlog here. I managed to stay keto the entire vacation, without too much effort. It was quite easy to stay keto actually. I did give myself a talking to before we came and I decided that I was going to do a totally keto vacation to show you guy that it absolutely can be done.  I thought that I was going to fail at the first hurdle when we got to the lounge in the airport. It was all carbs.
It would be hard to beat Chiang Mai for its combination of great November weather and low prices. Even though it's officially the start of the high season for hotels, the beginning of the month is usually very slow anyway, so bargains are common. Hotels in Chiang Mai are among the best bargains in the entire world, so even if you do have to pay full price for a room it'll be cheaper than a dorm bed in most European cities.
Those who adore the holidays and don’t mind the cold (the average high is around 48 degrees) might consider an end-of-year trip across the pond. Arguably Europe’s most festive destination, December in London promises charming Christmas markets, show-stopping Christmas trees, and streets covered in twinkling lights. A number of posh hotels, like 45 Park Lane and The Dorchester even have Christmas-centric packages available to get you into the holiday spirit.

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Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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