The 2nd option is a bit early in the year. The Greek Islands are cold and mostly deserted until mid April or so, and the good weather really starts in May or June. This is true in Mallorca as well. The Canary Islands are much farther south so they have acceptable beach weather almost all year, although you might get some cooler days in March as well. Even still I wouldn’t really recommend them for a younger person. In my opinion, the Canary Islands are pretty boring because the majority of visitors that time of year will be retired people from northern Europe who just want to sit in the sun. The nightlife tends to be cheesy and/or weak if you can find it at all. Let me know if you have any other questions. -Roger
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.
That’s an interesting question. On my main list of Caribbean destinations ranked from cheapest to most expensive, I have a list of the 6 islands that suffered heavy damage and are not going to be open for normal business this coming winter. But that leaves 26 other destinations on the list where things are totally normal. Fortunately for the industry in general, the busiest destinations such as Jamaica, Dominican Republic, and the Cancun area, are all still unscathed.
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.
There is no better time than December to discover a still (somewhat) under-the-radar part of the Caribbean. This verdant, five square mile island has seen a lot of activity recently, from a new mega yacht club to a Soho House to the Mandarin Oriental's first property in the Caribbean. More is on the horizon for this picturesque piece of paradise, but go before everyone else discovers it.
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.
As for the Northern Lights, Iceland is one to consider, and its Aurora Tourism sector is pretty famous. You can get a cheap flight to Iceland from London or most other large cities in Europe, and it’ll cost about the same as a flight to Stockholm or Oslo. If you want to stay on the continent, I’d think about Sweden, even though Norway has more northern area. Both are very expensive, but Sweden is a bit cheaper and easier to get around in.
The rainy season is still finishing during November in Central America, but a bit north and south of that it's dry enough to make visiting very worthwhile. Better yet, it's still low season for hotels in most places even though the weather has gotten nice. Latin America is filled with excellent bargain choices and it has some of the best places to visit in November.
If you are referring to days trips and that sort of thing, it will be much cheaper if you book once you get there. In Vietnam in particular it’s amazing how cheap tours can be if you book them through your hotel. I once did a 6-hour bus tour to Mỹ Sơn, which is near Hoi An, and I think I paid about US$6. It even included a boat ride and a basic lunch. That same day tour online would probably cost US$30 because the booking company takes a share and there is very little competition.
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.
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
Aside from Indonesia you might also consider Thailand, which has great infrastructure so it’s much easier to travel with young children. Phuket has by far the most options, and its rainy season usually ends in early November. For families I recommend Kata Beach and Karon Beach, which are both just south of the main shopping and nightlife town of Patong Beach.
If you are going for one week I wouldn’t go all the way to Thailand, but if it’s two weeks I think it’s worth it. It takes most of a day in each direction, but flights are often reasonably priced, and everything there is cheap once you get there. I’ve actually lived in Thailand for 6 months and have visited many more times and it’s actually very easy and stress free once you are there. All the important signs are in English and nearly everyone you’ll encounter as a tourist will speak enough English to help you as well. You can get around by train or VIP bus for cheap, or fly to the islands for cheap. It’s very safe there as well. You could spend a few days in Bangkok and then head to one of the islands or take a train up to Chiang Mai.

Thank you so much for the kind words and I’m always happy to hear that people find this information useful. As far as Turkey in December is concerned, I wouldn’t recommend it. I actually lived in a small town near Antalya on the Mediterranean for a bit over a year and I was surprised by the fact that almost everything closed down around 1-November and didn’t start opening again until March or April. Actually, I think Istanbul would still be enjoyable in December and so would Bodrum or any of the other larger cities including Antalya. But anywhere on the coast will be a ghost town and I’m pretty sure that Cappadocia would also be mostly shut for the winter. Ephesus probably stays open, but similar to Cappadocia, the attractions are all outdoors and they can get pretty fierce rainstorms in winter.
Europe in general and Greece in specific are not ideal in January because it’s cold and many sights are closed. I’d go to Thailand, which has a great variety of things to see and do, and January is the best weather month. Spend at least a few days in Bangkok and then either go to one of the islands like Phuket or Kho Samui, or head up to Chiang Mai for its temples and shopping and outdoor activities. You could even head over to Siem Reap to spend a couple days seeing Angkor Wat. Let me know if you have other questions. -Roger
But again, Vietnam can be a bit complicated for first-timers. Specifically, you need to book trains and tours through travel agencies, and Vietnam’s many travel agencies have a worldwide reputation for being hard to trust. They are all great salespeople but the product they deliver isn’t always what you expected. I spent 4 months in Vietnam and loved most of it, though I think it was much easier as a solo traveler who didn’t have a set schedule.
The December weather is actually warm enough to sit on the beach, but most people who come to Dubai tend to just relax and do a lot of shopping at one of the enormous and modern malls here. The restaurant scene is very interesting as well, and you can eat cheaply if you follow the local workers, or go to one of the hotel restaurants and get world-class cuisine.
Pay homage to the Native American heritage of the U S of A by taking in the sights and sounds of Arizona’s capital city for pure rest and relaxation before the holiday season. Phoenix anchors a sprawling, multicity metropolitan area known as the Valley of the Sun, which is highly regarded for its luxury resorts, vibrant nightclubs, designer golf courses, and long lasting sunshine and warmth—even through the winter months. Attractions include the Heard Museum and the Pueblo Grande Museum & Archaeological Park. Be sure to check them out!
Another tip is to look for apartments. If you’re visiting a large city, chances are they have plenty of new apartment buildings that are looking to rent out. Many of the larger hotel booking sites will offer you apartments for rent – and they’re very affordable. Not to mention, they’re much roomier and more than likely updated. You usually get a full kitchen, washing amenities (for laundry), a dinner table to sit and eat at, and a good sized bathroom that doesn’t make you feel cramped.
December might be the only month of the year in the Canary Islands where very few people would consider sunbathing. Still, compared to everywhere else in Europe, Tenerife is balmy. The largest and most English-speaking of the Canary Islands, Tenerife is no mystery to the hundreds of thousands of northern Europeans who spend a month or more here every year.
Oh, did you want a sunny tropical vacation that doesn’t require a passport? Done. Hurricane season is over, flights are cheap, and the water is still warm enough for swimming (and scuba diving). Almost all the tourists come here via cruise ship, which means you’re mostly not competing with them for hotel rooms -- Windward Passage, Emerald Beach, and the Bolongo are all open for business after Hurricanes Irma and Maria last year. On December 16 you can catch Jazz By The Sea down at Coral World Ocean Park, and on December 21 watch the St. Thomas Lighted Boat Parade, where contestants (boats) are judged on lights, originality, and holiday cheer.
Pay homage to the Native American heritage of the U S of A by taking in the sights and sounds of Arizona’s capital city for pure rest and relaxation before the holiday season. Phoenix anchors a sprawling, multicity metropolitan area known as the Valley of the Sun, which is highly regarded for its luxury resorts, vibrant nightclubs, designer golf courses, and long lasting sunshine and warmth—even through the winter months. Attractions include the Heard Museum and the Pueblo Grande Museum & Archaeological Park. Be sure to check them out!
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