Early in your message you say the last week of November, and then later you mention “late December,” so I’m not sure which it is. But if it’s late November, I think Italy could be a great option, as the weather there is still quite nice, at least in the south. You could go to Venice for a day or two and then Florence and Rome, and then maybe spend 5 or so days in Sorrento. I spent 5 days in Sorrento in mid November two years ago and the weather was very nice, even if it wasn’t warm enough to sit on the beach.
But if you wanted more to explore the area near Singapore then Malaysia and Thailand are the obvious choices. The three most popular stops in Malaysia are Malacca, Kuala Lumpur, and George Town on the island of Penang. I quite like all of those so it’s hard to recommend one over another. I really like Kuala Lumpur and have spent quite a bit of time there, but honestly compared to Singapore it seems a bit untidy and old fashioned. In other words, if you are tired of a big and busy city like Singapore, then don’t plan much time in KL. Malacca and George Town are both smaller tourist cities with great food and interesting sights. There is frequent and cheap bus service from Singapore going through Malacca and onto KL. Then more buses from there to Penang and onto Bangkok.
As the year winds down the parties amp up, none more so than in Scotland’s capital, where Hogmanay celebrations see flaming torches, fireworks displays and night-long parties take over the usually quiet cobbled streets. Slightly more sedate, the Caribbean’s southernmost island Trinidad simmers with stirring Spanish-style musical performances as the locals usher in the start of the dry season.
From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
Cancun is at the north end of the Riviera Maya, which also includes the island of Cozumel, so this is a huge area with over a thousand hotels to choose from. All that competition keeps prices down until the high season begins, so November is still a buyer's market. There are even ruins nearby and other cultural opportunities, so it's not all about sitting on the beach here. If you prefer a high-rise hotel overlooking a beach then stay in Cancun itself, but if you prefer to stay in a friendly town with many restaurant and shopping choices then head to Playa del Carmen, just a bit to the south, instead.
Costa Rica is kind of the Thailand of Latin America in that they have great tourist infrastructure and it’s the easiest place to get around. They also have a lot to offer with the beaches on both coasts and many natural sights and activities, plus of course the Arenal volcano, which is a really nice area. San Jose is best as a place to just pass through on your way somewhere else.
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.
A few months ago, my girlfriend and I went on a small vacation through Portland and Seattle. I wanted to document all of the food I was eating to share the experience and to provide some tips and tricks with all of the curious folks out there. Being ketogenic while being on vacation is one thing – but eating well while staying keto is another, and I’ll show you how to do it.
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.