As you suspected, this is a tricky one. Most of the places that would work for you are having a very rainy month in November, so it’s not a good time. Thailand would actually be a good choice if you can deal with the travel time. The rainy season there ends in October and yet the crowds don’t start appearing until December, so you get low hotel prices with nearly perfect weather. As mentioned, all of the good options in Central or South America have a wet season in November. Argentina could be a good option, as November is late spring there, and it has everything you are looking for. The flights to get there are also fairly long though.

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.

Another destination that might not exactly have “great” weather in December, yet deserves to be on the list, Sharm el-Sheikh is famously Egypt's most popular Red Sea beach resort. Those following the news might still hesitate to book a trip here, whether that is a rational decision or not. But at the very least this is one to consider in the future, as it's an amazing bargain once you get here.


This sounds like a really fun trip you have in mind. I think the challenge is that most of Europe is much closer to 50F than 80F in November, and a good chunk of Europe is already colder than that. I’m running a new series highlighting the best places in Europe (and Asia) to go each month of the year, and I think that the best Europe destinations in November would be helpful to you. Another tricky thing is that you’ve been to many of the warmer places already, and I do understand your boyfriend’s desire to go someplace that neither of you have been.
That definitely helps! Though I think I was quite unclear in the first place. Being in the same region is definitely not a constraint. We’ve been considering Africa as well, for example! Also, a couple of days of beach time is also sort of desirable, and we’re not really into visiting cities as such. Ideally, we wish to have some time to spend on beaches/resorts/hotels along with some time in a place like a safari or something.
That definitely helps! Though I think I was quite unclear in the first place. Being in the same region is definitely not a constraint. We’ve been considering Africa as well, for example! Also, a couple of days of beach time is also sort of desirable, and we’re not really into visiting cities as such. Ideally, we wish to have some time to spend on beaches/resorts/hotels along with some time in a place like a safari or something.
Hotels in Buenos Aires are starting to reach their summer peak prices in November, especially toward the end of the month, but still they are a fantastic bargain by European or North American standards. The weather in November is also pretty much perfect, and while there's always a threat of rain in BA, it's mostly an indoor city so it shouldn't be too much of an inconvenience.

You’ve got a pretty good budget so you can afford to go almost anywhere, assuming you are okay with renting one or two houses or villas instead of 4 hotel rooms. If you are willing to fly all the way to Asia, your best bets would be Bali or one of the Thai islands, probably Ko Samui or Phuket. In all of those places you should be able to rent a house or villa near the beach and then do activities and day trips very easily.
If I were you I’d fly into Bali and spend a couple days in the Kuta area to get your bearings and then head to Ubud, which is in the foothills and easily reached by shuttle bus. It’s also fairly crowded, but it’s still quite nice and there are scores of little spas and yoga places and that sort of thing. Then after a few days there, head up to the northern coastal town of Lovina, which is sort of like how Kuta was 25 years ago. It’s still only partly developed and there are still many open spaces, which is no longer true in the Kuta area. It’s cheaper than Kuta, and somewhat like Boracay in how mellow it is. You could also take a ferry from Bali to the island of Lombok, which is the next large one over. Things there are also more like Boracay and less chaotic than the Kuta area. Again, I really love Bali and still recommend it, but unless you are an Australian surfer, it’s best to stay somewhere other than the general Kuta area.
Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.

On the hunt for a non-traditional ski vacation? Look no further than the Japanese Alps. According to American Express Travel, the region has seen an increase in bookings during the holidays in recent years. And while December has historically been less popular than Japan’s peak season—April-November—adventurous travelers are now intrigued by the wilderness of Japan in the winter. The Hida, Kiso, and Akaishi alps are home to indigenous snow monkeys, volcanoes, and lava plateaus, plus, visitors are drawn to the area for its pristine ski offerings, natural hot springs, and rural hiking.
If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger
As for alternatives you might consider Argentina, where of course it will be late spring in November. Buenos Aires is a wonderful city and recently they’ve been going through a financial meltdown again so their currency has dropped a lot, making things unusually cheap again. You could spend 3 or 4 days in Buenos Aires and the rest in the Mendoza wine country or Iguazu Falls or Bariloche for some adventure. From everything I have heard it’s all safe and civil there, so it’s just a matter of the local currency going down in value.

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.
There are always those travelers who celebrate the end of summer and the opportunity to don a sweater and take out the wool scarves and quilted jackets. For them, Iceland would be a perfect destination, with a chance to see the Northern Lights and adorable sled dogs. Montreal is another place with a winter chill, and at the end of the month, you might even find an early Christmas market. San Antonio gets into the holiday spirit at the end of November as well. Sedona offers chilly nights and gorgeous scenery, while Hilton Head Island still enjoys autumn weather and activities.
You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
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