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.
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.
Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger

Hawaii, as you probably know, would be great for what you have in mind, except that there are no cheaper options there at all. After that I agree with you that there are places in Mexico that could work. One in particular that I like a lot is the area around Playa del Carmen, which is just south of Cancun. It’s a lively and tourist-friendly town, instead of a strip of big hotels like Cancun, and there is a wide range of activities and accommodations in different price ranges.
One reason that Vietnam isn’t as popular as it could be is that travelers often feel a bit hounded when they are there. For some reason, those in the travel business in Vietnam (working at travel agencies where you book tours and such) make tourists feel like they are being hustled. They are rarely 100% honest with what they tell you or about the prices they are charging. Still, it’s an amazing country and it’s also incredibly cheap, even if you end up paying a bit more than you were supposed to. I highly recommend it, and it won’t be a problem if you realize before you get there that you can’t take everything at face value in the way that you usually can in Thailand or Bali. Quality of hotels for the money is also very good.
Just came back from Luang Prabang, Laos. Cheap and easy to navigate. If with kids you can do an elephant training camp few days. Airport 15 min from hotels and just 2 minutes to get visa (30USD). Not so much to see, but nice vibe and cheap. If you have to choose between Luang Prabang and Siem Reap, Siem Reap has more to offer, but is much hotter than LP in December.

As chilly temperatures arrive in the northern hemisphere, it’s spring in Buenos Aires, an ideal time to visit. The city’s jacaranda trees are decorating the streets in purple petals, hotel prices are attractive, and the weather is comfortable and dry. A cruise along the Rio de la Plata would be a good place to start, for a relaxing overview of neighborhoods, homes, markets, and the waterfront. On Sundays, get some authentic local flavor at Feria De Mataderos, about an hour from downtown, with gauchos on horses, craft vendors, musicians, tango dancers, and regional foods.
Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
Myself and my girlfriend are looking at travelling to a sunny destination during the first 12 days of December. We like beach and city vacations. Being from South Africa where it is warm in December we would prefer something different to our own culture. We’ve been to Thailand and Malaysia but never India, Sri Lanka or Vietnam. What would you recommend? Thanks Esteen
We are looking to explore warm Central American destinations safe for kids and affordable in price. We love beaches. Not in the typical sun-bathing type of way, but rather appreciating the raw beauty of the nature. We also like to eat out and having activities for the kids and as a family would be excellent. Could you suggest a destination that fits the bill? Central America appeals to me but open to other suggestions you may find worth mentioning.
Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex. 
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