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
Another consideration is that Thailand is generally easier to get to with far more flights that are often cheaper, and Thailand also has FAR more beach options because of its long southern coastline and especially the islands. The posh beach areas on Phuket are typically the most expensive beach hotels in Thailand, but there are other more remote beaches in Phuket with lower prices so it’s worth a look. Aside from Phuket you should also look at Ko Samui, Ko Pha Ngan, and Ko Phi Phi. You might also look at the town of Pattaya, which is the closest beach resort to the Bangkok Airport. Parts of town have a lot of single foreign men in certain bars at night, but most of the town is actually quite family friendly and very good value. Let me know if you have other questions. -Roger

If you wanted to spend maybe 7 days outside of Singapore, I think I’d do 2 or 3 in Malaysia and then the rest in Thailand. Bangkok is another huge city but it’s also somewhat exotic compared to the other two, and much cheaper as well. Or if you wanted to spend some time on a beach you could instead go to one of Thailand’s islands. Phuket is the easiest to reach, but it’s not very interesting. Kho Phi Phi or Kho Samui are probably better choices because they really feel like islands (Phuket is more of a peninsula) and there is still plenty to do.

The Brazilian currency has been falling in recent years, and if this trend continues then Rio de Janeiro will be squarely back into the bargain category. It's certainly not as cheap as it used to be, but for the amazing beaches and scenery it's easily worth it as long as you plan well and stay safe. In fact, Rio has some of the best beaches in November anywhere in the world, and a vibrant city right next to them.

If you’re a bit more on the timid side, you can always use Yelp and TripAdvisor to get good insights on places people have visited. As a disclaimer, some of the ratings may not be accurate on these sites, so make sure you go through and read some of the more recent reviews that people have written. We did this for a few of the places we visited and had no issues.