Sri Lanka doesn’t really have a good infrastructure for budget travelers at this point. There are loads of nice hotels if you are willing to pay US$40 or more per night, but almost nothing below that except for a few hostels. I haven’t been to Palawan but I have been to Boracay and Palawan can’t be too much cheaper. Boracay doesn’t have many budget options either, so my guess is that Thailand or Cambodia is your best bet.

The rainy season in Cartagena winds down by early November, so this is an ideal time to come, especially toward the end of the month if you can get cheap airfare before and/or after Thanksgiving. The temperatures are pretty much the same here every day of the year, so the key is to work around the autumn rainy season to when it's dry but before hotels fill up.
Hurricane season officially ends on November 30, so it's safe to visit the Caribbean. There's good news for skiers, too, since most of the northern hemisphere is heading toward winter as the year comes to a close and mountain regions become dusted with snow. Couples who prefer a warm-weather vacation in November or December will have to travel south to find balmier temperatures — and prices begin their uphill climb toward the high season.
In SE Asia you have many choices, but probably the best choice for a family would be Phuket, Thailand. It’s more expensive than Goa, but the infrastructure there is much better. Patong Beach is the biggest town on the island and the main tourist hub, but for a family I’d recommend Karon Beach or Kata Beach, both of which are just a bit south of Patong, and both lovely.
My first thought was Goa, which you say you’ve been to before, but maybe you don’t realize that there are about 20 different beach areas that are different from one another in terms of vibe and types of visitors? Personally, I found that Anjuna and Vagator were both kind of mellow but also busy enough and easy to meet other people. But if you don’t like those, there are many different beaches in the south, which I’ve heard are also great and draw different groups. It’s something to think about because it doesn’t get much cheaper than Goa for beaches anywhere in the world. -Roger
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 sizzling summer days are in the past, and it’s time to enjoy your favorite outdoor activities whether they’re hiking, window shopping, al fresco dining, relaxing poolside, or strolling through Palm Springs — an adventure in itself. The Uptown Design District boasts home décor stores, boutiques, retro and resale shops, some specializing in the mid-century modern style that Palm Springs is known for. Further downtown, restaurants, small shops, and designer boutiques invite diners and shoppers. 
Never thought of Moscow as a Winter destination! It is quite the place to go especially after the world cup hype. I second Rajasthan, India as one of the best places to travel in December. Love this list, Wendy. I have even listed Rajasthan and other offbeat places to travel in December and January over here: https://www.thegonegoat.com/inspiration-and-tips/2018/11/29/the-best-places-to-travel-december-january
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.
Keep Snacks Handy When You are Out – This was my snack stash for Disney World. I had Macadamia Nuts, Walnuts, Pecans, and low carb bars. I made sure to chill the water bottles in the freezer beforehand so that as they thawed throughout the day, we had cold water. When hunger hit, instead of falling to temptation, I just grabbed my bag of snacks before I got HANGRY. Doing so made it so much easier to make keto/low carb choices at mealtime. I kept my snacks simple because we already had enough to bring with us (if you have a baby and a toddler you know what I mean). I saw lots of people with small coolers who were snacking on fresh veggies and deli meats, but, again, my goal was easy breezy. You can find a great list of Keto/Low Carb Snack ideas here for inspiration if you prefer a variety.
If you are looking for a place to go abroad for a few months starting in early December, you are right on the money with Thailand as the best starting location. The weather is really nice that time of year, and it’s quite easy to keep things extremely cheap if you need to. Many of us in the travel writing community have spent months or years traveling around southeast Asia, and I’ve probably spent close to two years there myself. Bangkok is the obvious place to start and it’s an amazing city. After that you can either go north to Chiang Mai and Chiang Rai and then over to Laos, or you can head south to one or more of the islands. Cambodia has a lot to offer, and especially in Siem Reap, and Vietnam can be entertaining for all three months of your first visa there.
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
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