If you are mainly just looking to relax, you've found the perfect place, with warm weather and amazing off-season deals. The all-inclusive resorts tend to be much cheaper in the long run, although they do make it more difficult to experience the local culture and explore the whole island. If you don't care about leaving the resort and you want the best all-inclusive value in the Caribbean, head straight to Punta Cana, which is mentioned just below.
Another reason to consider Dubai is that the busy airport has cheap non-stop flights coming in from almost every major airport in Europe and Asia. As a result it's popular to book long weekend trips of 3 or 4 days to Dubai, where you can enjoy some sunshine and shopping before flying back home where it gets colder by the day. You might also consider stopping for a few days in Dubai and then moving onto somewhere else with cheap direct flights such as the Maldives.
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.

New Zealand will also be crowded, but the country is otherwise mostly empty so it is still wonderful. You could fly to Auckland for one day or so and rent a campervan/motorhome. Drive it for 3 or so days on the North Island, and then onto the ferry to the South Island for the rest of your time. The South Island is far more scenic and less crowded. You’ll be doing some driving and looking, but after a few hours of that you can stop at a campground and have plenty of things to do such as hiking or water sports and much more.
Oh no. I don’t mind rain but that would be a little disheartening. I come from a tropical place and it wasn’t until I moved to Canada that I realized that “rainy seasons” don’t really mean much. More so, I went to Punta Cana last October during the cold period and it was gorgeous every day, and what little rain fell was usually overnight or little drops that you could stay on the beach unbothered.
Overall, I’m declaring this vacation a great success! Not only did we have a wonderful time at the parks riding all the rides and enjoying the shows, I did not feel at all deprived or put upon food-wise, and not even once did I go hungry. All but one of our meals, including those at the hotel, were counter-service only establishments and I was able to find something filling and tasty for each meal. After this experience here are my recommendations for eating on vacation:
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
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.

I too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
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.
From England I would say your cheapest and best late December destination with warm weather and reasonable prices is going to be Phuket. There are some other Thai islands that might be a bit cheaper, but they would be more complicated to reach, and they’d have fewer activities for the boys. Here are some Phuket resorts good for families. You can see that the price range is wide from cheapest to most expensive. In late December it’s peak season so you’ll pay at or near the top of those ranges.

Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
Montego Bay is home to one of the Caribbean's busiest airports in addition to a few hundred hotels and resorts, so it's an ideal destination for even a shorter getaway in November. The rainy season is over but the busy holiday peak season doesn't begin until just before Christmas, so the weather is perfect and hotel prices are still very low. Flights should be cheap from most hub cities as well, so even a long weekend is within reach for budget travelers this month.
From England I would say your cheapest and best late December destination with warm weather and reasonable prices is going to be Phuket. There are some other Thai islands that might be a bit cheaper, but they would be more complicated to reach, and they’d have fewer activities for the boys. Here are some Phuket resorts good for families. You can see that the price range is wide from cheapest to most expensive. In late December it’s peak season so you’ll pay at or near the top of those ranges.
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.
On the morning of our last day we hit the hotel cantina again for another round of breakfast bowls and bacon (Meal 5), which I had with fatty coffee. Afterwards we headed out for our final day. After riding a few things and checking out some of the tours, we found a place for a late lunch/early dinner at around 4 pm. This was the only sit-down, table service place we patronized on the entire trip and it was worth it. The menu didn’t seem to have a lot to offer the carb-conscious, but after explaining briefly to my server that I avoid carbs and sugar, I settled on the Kobe beef burger, bunless, and the server offered to replace the side of fries or rice with a bowl of stir fried veggies. My plate arrived (Meal 6) and looked gorgeous! The veggie bowl consisted of onions, peppers, mushrooms, snow peas, baby bok choy, and some carrot sticks which I mostly ate around. After stirring in a smidgen of the offered soy sauce and Sriracha, I must say I was greatly pleased with this side. The chef also garnished my plate with a small sample of cucumber salad, which was delicious. The burger was as thick and round as a steak and was probably the best restaurant bunless burger I’ve ever had. It was served with a sesame-soy sauce mayonnaise as a condiment which really complimented the burger well. This was probably my favorite meal of the trip and it was well worth the price and effort of sorting through the menu.
November is a perfect time to visit Bermuda, with temperatures in the mid-70s and pink sand beaches that are less crowded than in high season. There are many ways to explore the 21-square-mile island, from under the sea where you can snorkel or dive among coral reefs or shipwrecks to the Bermuda Railway Trail, an 18-mile abandoned rail bed that winds through scenic landscapes and shorelines. The Crystal Caves take you into an underground world with a subterranean lake and white limestone stalagmites. The 36-acre Botanical Gardens, established in 1898, inspired John Lennon during a two-month Bermuda stay that led to his Double Fantasy album.
I’m hearing very mixed things about Cuba visits. The main downside for Americans is that you still have to go as part of a package deal, and those packages are all incredibly expensive for what you get. It sounds like the Cuban government is charging very high taxes and fees on companies selling tours to Americans, so they are really only popular among people who are especially curious about visiting Cuba. In other words, they are poor value unless it’s at the top of your list already. I hope this helps. Let me know if you have any other questions. -Roger

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.
As for Indonesia vs. Philippines, I’ve been to Bali quite a few times but I haven’t been to Bandung. And for the Philippines I’ve spent time in Manila and in Tagaytay just to its south, and I don’t think I’d recommend those for a longer trip. And I also spent two weeks on Boracay Island, which is quite nice, but it’s small and also a place I wouldn’t recommend for a longer trip like yours. For information on Indonesia you might go to my friend’s site – travelfish.org – which is an excellent resource. Unfortunately, they don’t cover the Philippines yet. Best of luck with what you end up doing. -Roger
Also, as far as I hear, the worst that ever happens is they take your stuff. So if you leave your passport and most of your money in your hotel room, and keep your phone or camera hidden most of the time, there isn’t much to lose. I’m making it sound worse than it is really. I wouldn’t hesitate to go to Rio again, but of course I’d be aware of those few situations to avoid.
Vacationing to Sicily during Italy’s traditional “off-season” has been trending in recent years, according to American Express Travel. What gives? Well, for starters there's Sicily's fabulous Mediterranean setting, as well as its rich baroque aesthetic and festive Catholic traditions. Plus, the crowds are more manageable than they are in the summer, which makes travel for families and large groups a breeze.
However, I also happen to be an athlete and about a month ago I reached the point where I had almost no power, no energy, constant hunger (and “hanger”) and cravings for practically anything bad like alcohol, sweets, carbs, artificial sweeteners or energy drinks. I tried to fight it. I started over multiple times. At one point I just couldn’t stick to any sensible dietary routine for longer than a day or two. Intermittent fasting, OMAD (one meal a day), TMAD (two meals a day) and keto all seemed to stop working.
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.
While Cancun has become the king of the Mexican beach resort towns in the few decades since it was formed, it's only one of many, and all of them on both coasts have very nice weather in December. In fact, Cancun is probably the most expensive of them, so especially if you are coming from the west coast you are better off in Puerto Vallarta, Acapulco, or Los Cabos instead.

Every year it goes the same way. My mom calls me up a few weeks before Thanksgiving and asks me, “You are bringing green bean Casserole this year, right?” before she launches into a chorus of “You have to! No one else makes it just like you do!” Green beans have become “my thing” around the Thanksgiving holiday, and it’s the dish that I am expected to bring to dinner each year.
There are snack stands everywhere at the theme park, and I can tell you from the experience of at least yearly visits that most choices at the stands are decidedly NOT keto-friendly. In recent years they’ve added what I’m sure they consider “healthy” choices, but most of those consist of yogurt and fruit with dip. You may, upon occasion, come across some carrots and celery with dip, but it’s very hard to find.
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.
In November you can find excellent resort deals all over the Dominican Republic, but Punta Cana is typically the first choice, especially if you are looking for an all-inclusive resort with all the luxury extras at a great price. The resort is actually a collection of little beach areas on the eastern tip of the island, so it's very secluded and well away from some of the confusion closer to the capital city.
Orlando’s theme parks are a major draw for families (and big kids, too!), but this iconic experience doesn’t necessarily come cheap. During the pre-Christmas November lull, however, hotels often offer attractive discounted rates, meaning potential savings and – more importantly for the kids – less time spent standing in line. Those looking for a more alternative American adventure should consider the island of Puerto Rico in November. While there’s a chance of rain (but a greater chance of balmy beach-lounging days), the out-of-season discounts are as appetising as the island’s take on Thanksgiving dinner: turkey stuffed with mashed plantain.
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