Hi Roger, Just wanted to thank you for taking the time to compose this list. I always refer to your destinations (with great weather) lists prior to booking future-dated vacations. I was a little worried that you didn’t mention Bali but there was more than enough in the comments to reassure me that it would be a great spot to visit in December. I also saw your other post for places to visit over Christmas and NYE. Thanks again!
If you have a flexible schedule, or if you just happen to have some time off in November, you are in luck. This is honestly the best month of the year for finding cheap destinations that also have fantastic weather. Since most people don't start their winter travel until mid or late December, it means crowds are small and hotel prices are low through huge sections of the travel world. Those wondering where to go on holiday in November have many great choices at bargain prices, although airfare may cost a bit.
Unfortunately I’ve only been to Cartagena in Colombia, although I know of some travel bloggers who live in Medellin and love it there. The mild weather year round is one reason people love it. I don’t speak much Spanish, which is a problem in much of Latin America, but evidently there is a pretty big scene of various expats and English speakers, so Spanish isn’t so critical. In other words, I like the sound of your idea and I imagine it’ll be great, but I haven’t been there yet so I am really not qualified to give real advice. Best of luck with whatever you choose. -Roger

I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -Roger
If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.

My top recommendation would be San Juan, Puerto Rico. It offers a wonderful mix of history and culture and nightlife and great food, alongside excellent beaches and abundant activities. Hotels and rental apartments are mostly in the mid-range for the Caribbean, but food and drinks and most other things are great value. You could get a place in the Condado area, which is close to the lovely Old San Juan neighborhood and plenty of nightlife all around. And then perhaps you could rent a car and stay for a few days at one of the smaller beach towns elsewhere on the island. You wouldn’t even need a passport, although it does feel fairly exotic while you are there. But because it’s part of the US, it’s also well organized and safe. Most people you’ll meet will speak at least some English, and many are fluent, so it’s easy even if you don’t speak Spanish.


If a warm weather getaway sounds appealing, consider seeking the sun in Cartagena where summer is approaching. The South American city offers history, Christmas spirit, and unique gifts for holiday shopping. Sun-drenched Phuket, Thailand’s popular island, is a place to relax during the day and party at night. St. Bart's in the Caribbean is recovering nicely from hurricane damage, an ideal spot for a winter vacation. Miami’s December weather is perfect for a warm Christmas, and Art Basel, early in the month, is an exciting time for fans of contemporary art. In Santa Barbara, a few days of pampering might fit the bill, or you can join in their holiday festivities throughout the month. Death Valley, in the middle of the Mojave Desert, offers a respite from the crowds and a chance to enjoy quiet days and starry nights.
My top recommendation would be San Juan, Puerto Rico. It offers a wonderful mix of history and culture and nightlife and great food, alongside excellent beaches and abundant activities. Hotels and rental apartments are mostly in the mid-range for the Caribbean, but food and drinks and most other things are great value. You could get a place in the Condado area, which is close to the lovely Old San Juan neighborhood and plenty of nightlife all around. And then perhaps you could rent a car and stay for a few days at one of the smaller beach towns elsewhere on the island. You wouldn’t even need a passport, although it does feel fairly exotic while you are there. But because it’s part of the US, it’s also well organized and safe. Most people you’ll meet will speak at least some English, and many are fluent, so it’s easy even if you don’t speak Spanish.
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 your Europe trip, I highly recommend spending 3 nights in any city you visit. If you change cities every day or every other day you’ll end up spending most of your holiday on trains or in airports rather than seeing the places you flew all that way to see. So if Amsterdam and Barcelona are musts, I would add exactly one other city if you’ve only got 9 days. Unfortunately it’s not on your list, but the best and easiest one to add between them is Paris. There is a train from Amsterdam to Paris in a bit over 3 hours, and another high-speed train to Barcelona from Paris in 6 hours 27 minutes with no changes. Paris is easily one of the most impressive European cities for tourists, but if you’ve been there before and don’t want to go again you can obviously choose something else.


Of course, the Caribbean has its own share of problems. As I just mentioned to another reader, my list of Caribbean destinations from cheapest to most expensive has 32 entries and only about 6 of them were damaged by the recent storms. I would probably choose one of those instead. November is still technically the final month of hurricane season, but November storms are extremely rare. And the islands closer to South America haven’t been hit in over 50 years or so, such as Aruba, Bonaire, and Curacao.
It’s going to be pretty cold in December all over Europe, although not quite so bad in the south, of course. As far as where to go, I’ll refer to our Europe 3-star traveler index, which lists every major city in Europe from cheapest to most expensive. The price is the typical daily expense per person for a couple traveling and staying in 3-star hotels. Once you scan through that list you should have some ideas.
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.
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.
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