If it’s not on there already, a visit to Iceland should be added to your bucket list. November will be chilly, but you’ll miss the high season crowds and arrive during peak viewing season for the Northern Lights (November through March) when the nights are longest. The infusion of colors, mostly bright green and at times a mix of purple, pink and red, is a breathtaking sight. November is prime time to visit the gorgeous ice caves, crystal and sparkling in stunning shades of blue with cave tour options that include hiking or snowmobiling.

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.

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.
I’ve done most of my travel as a solo, and I’m now a couple years older than you, so I know exactly what you are asking about. If you had even 2 full weeks I’d suggest going to southeast Asia, but as you say, the travel time could be a killer for a shorter trip. Still, it’s a unique experience with a lot of positive aspects to it, so you should keep it in mind. If you are still considering it, I’d suggest flying to Bangkok for 4 days or so, and then spend the rest of your time on one of the islands such as Kho Samui or Phuket. If you want more information on that, let me know.

Let’s get started. For the November trip you are going to have a lot of competition for those flights and hotels because those are prime Thanksgiving flight dates. I would normally recommend Puerto Rico, but they won’t be ready for visitors until next year from what I hear. Just a few days ago I published a new article on which Caribbean destinations have no hurricane damage. There are a lot of great choices, including all of the busiest ones, that were untouched by the storms. You might also consider Cartagena, which is probably the cheapest option once you get there. It’s got a wonderful walled historic town area, and it’s a short bus or taxi ride to the modern area with beach hotels and such. The sand there isn’t great, but the value is very good. I wouldn’t go outside of Cartagena at the moment.

Thank you. If you are looking for an all-inclusive or large resort hotel on a beach, you can’t do any better than Punta Cana for value and facilities. You can also find really nice resorts in the general Cancun area, and the flight would probably be cheaper, but the nightly rate would be quite a bit more. Both have really nice beaches, although with Cancun you have to pay attention to the specific location because not every resort is on a wide stretch of sand.
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

In India I’ve always had good luck with the trains by booking at least a couple days in advance, and also being flexible and only going when an AC3 ticket is available. As you know, the actual train stations are nightmares. But every hotel has a person who can fetch a ticket for you by going through the back door and bribing someone at the train office. Like a AC3 ticket might cost US$20, and for an extra US$4, your hotel will go buy it for you and it’ll be waiting at the front desk later that day. It’s a pretty sweet system.
It’s unfortunate and heartbreaking how many times I have recommended San Juan, Puerto Rico in the last few years. Once they get the power back on I’m sure it’ll be back to normal fairly soon after that, but I’m guessing probably March or later. And fortunately, Nate missed the Cancun area for the most part. Have you considered somewhere in the Cancun/Playa del Carmen/Cozumel area? I’m particularly fond of Playa del Carmen, and that flight to Cancun should be pretty reasonable for you.
This classic Thanksgiving side came from Julia Child. We don’t see many creamed vegetables any more, except maybe creamed corn or spinach, so this might be a bit of a novelty. And it’s delicious. If people complain about the richness, just remind them that Thanksgiving dinner is supposed to be a feast, right? (And you can get by with an awful lot be invoking the name Julia Child).
If you didn’t want to go to Asia you could instead consider the ABC islands, which don’t get much rain and haven’t had a major storm in many decades. Aruba, Bonaire, and Curacao are known for good snorkeling as well and you’d get good hotel rates that time of year. Two weeks might be a long time to spend on those islands though, so I would go to Asia if you can. Late November is a perfect time of year for a visit there, and you can even include a few days in Siem Reap to visit Ankor Wat. Let me know if you have any other questions. -Roger
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger