Yes, these lists are reviewed and updated at least once a year. I’ve been adding new cities each year and even removing a few that have become too expensive to be on a “cheap” list. Personally, I’m an obsessive travel planner (which is why I do this for a living) and I like planning at least a few months in advance. You usually get the cheapest flights around 3 months out, although it can range from 2 to 5 months for longer flights. In other words, now is a great time to plan a November trip.

More good news comes with the fact that there are two other great resort areas that are each about 90 minutes by shuttle from Montego Bay Airport, so you can almost as easily reach Ocho Rios or Negril, both of which have a different vibe that you might prefer. Bargain hunters will also find pretty amazing prices at the all-inclusive resorts, particularly those in Montego Bay and Ocho Rios. If you prefer a quiet beach area lined with smaller hotels, restaurants, and bars, then head to Negril.
In South America, and you start getting into some longer flights here, the best and safest places are Argentina, Peru, and Chile. I’m not sure if this helps you much, but at least it should let you know that you were thinking along the right lines already, and there are no obvious places that you’d overlooked. Let me know if you have any other questions. -Roger

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.
The island has made a miraculous comeback following Hurricane Irma, and by November, nearly all of the restaurants, villas, and hotels will be back up and running. Most regulars missed out on holiday season in 2017, however, December is bound to be crazy—but if you plan a trip just before the chaos, you're golden. Many of the luxury properties that were damaged have completed renovations, so expect everything to be shiny and new. While you really can't go wrong with any of the hotels, we're partial to Le Toiny, thanks to its uber-private accommodations, spacious villas, and over-the-top attention to detail.
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
When it comes to flights over the Christmas holidays, you should book as early as possible. The airlines know they can fill every seat at a high price so they don’t have an incentive to lower fares like they do for flights in January or February. Air Asia now flies from the US to Asia and at good fares. Aside from them it’s just the major airlines as well as some Chinese airlines that do those routes.
The other place that comes to mind is Croatia, which also has reasonable weather in November. I’d recommend focusing on Split, which has many similarities with the more-famous Dubrovnik, but it’s easier to reach, much cheaper, and more authentic because Dubrovnik has become kind of cheesy as a cruise port. You could even take a bus to Mostar or Sarajevo in Bosnia for a couple days. The coast in that area is beautiful and there won’t be many other tourists that time of year. I hope these ideas help. Let me know if you have any other questions. -Roger
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
Since you might be open to flying then another nearby option to consider is Siem Reap in Cambodia. It’s a pleasant tourist town on its own, but it only exists as the gateway to the amazing Angkor Wat temples nearby. Those temples are by far the most dramatic and memorable tourist attraction in southeast Asia, and I think your daughters are old enough to appreciate it all. But again, the town of Siem Reap is nice with plenty of other things to do, so it’s a great all around stop.
The idea of holidaying in a country where the depths of winter are approaching may seem a little counter intuitive but stick with us. The aurora borealis, or Northern Lights, is the best light show on Earth, and a trip to Iceland in November is the perfect ticket to see them. Explore thermal geysers, stunning waterfalls, and epic glaciers by day then stay up late and watch the skies dance with green light by night. Just make sure you pack your thermals though – the average day time temperature only reaches highs of 4c (40F)!
This popular island in the Andaman Sea boasts mountains, rainforests, white sand beaches, nightlife, and a range of hotels from casual to ultra-luxury. Watersports of all kinds are popular, with snorkeling and scuba diving among the colorful fish and coral reefs a favorite. Boat trips take visitors to smaller nearby islands and among the limestone cliffs, caves, and karsts — steep limestone structures rising from the clear aqua sea. The white marble “Big Buddha” statue, nearly 150 feet tall, on top of Nakkerd Hills is visible from miles around, and it provides a stunning viewpoint. The island has been settled from early times and through the years with migrants from India, Arabia, China, Portugal, Sri Lanka, Netherlands, France, and Great Britain, all attracted by Phuket’s natural resources. Old Phuket Town’s shrines, temples, museums, shophouses, and buildings provide some evidence of the island’s history. Today, for lively nightlife, head to Bangla Road at Patong Beach for restaurants, pubs, music, open air cafes, and street performers. For many visitors, Phuket’s beaches are the main attraction, and with more than 30 around the island along with ideal December weather, everyone can find the perfect spot for sunning and swimming. For the ultimate in luxury, the beachfront Banyan Tree Phuket offers villas with private pools and open-air bathtubs, an award-winning spa, several dining options, golf, and a tranquil saltwater lagoon.
From November through February there are literally no European cities that could qualify as having “great weather.” We list Tenerife below because it's technically in Europe, although not really much of a cultural destination. Antalya, Turkey (which technically isn't even in Europe), has the closest thing to a sunny climate with acceptable temperatures. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
Without knowing more about your interests, my top suggestion would be to focus on Sydney and Melbourne and the areas around both. The Blue Mountains near Sydney are also nice for a couple days or so. The main challenge you’d have in seeing a lot of Australia is that it’s all so spread out. You can hire a car for Melbourne and Sydney and that whole area, but it’s better to fly to get to Uluru (near Alice Springs) or Brisbane or Cairns/Great Barrier Reef or Perth. You’d be driving for days in between those places if you started from the southeast area where most people live.

While it's true that it might be a stretch to call Cusco's November weather “great,” this is perhaps the best month of the year to visit, and the weather is quite good anyway. The high season for hotels in Cusco ends in October, yet the rainy season doesn't begin until late December, so November is that perfect combination of small crowds, low prices, and very good weather.
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 is the end of the rainy season in Boracay, but by the middle of December you would probably only get a few quick tropical showers a week. Room rates are a bit lower at that time as well, so it can be a great time to visit. If you were looking for a place to go for 2 or 3 days, I wouldn’t recommend it because it does take some time to get there and you could be a bit unlucky with the rain. But if you are going for longer than that I’d highly recommend it. It’s a wonderful little island that feels like you’ve gone back in time to before mass-market tourism in places like Phuket.
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.

Unsurprisingly, the end of December is the beginning of the peak season for resort prices, so those who are able to come earlier in the month will be getting better deals. Still, the all-inclusive resorts are locked in heavy competition all year so this area can be a great deal compared to the alternatives, even in high season. If you are looking for where to go in December for an all-inclusive beach holiday, this is your best option for most people.

I am from South Africa and our family are planning to travel to Thailand in December for 30 days. What ittinary could you suggest. Our Start off would be Bangkok (2 days then take overnight train to Chiang Mai stay about 3 days not sure then fly to Phuket but dont want to spent time their. What Islands can you recommend? Is it worth it to perhaps consider to work in a trip to Cambodia or Vietnam or even Malaysia.

Needless to say, Australia is a huge country so you could spend 6 months there and not get bored, or you could spend one week there and barely see any of it. The obvious destinations are Sydney and Melbourne, both with plenty to do for non-beach people. Melbourne is known a bit more for culture and food, while Sydney is more pleasant and still very interesting. There is also the Great Ocean Road, which is a very scenic drive just a bit south of Melbourne.


The only other suggestion I have, which gets almost no rain in November, is Goa, India. There are about 20 different beach areas in Goa, and some of them (Anjuna and Vagator) are famous as party beaches, while many others are more mellow and family oriented. It’s also very cheap and beach massages and that sort of thing are excellent value. Let me know if you have more questions about that. I hope one of these things works out for you. -Roger

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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