My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger
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In colder weather it’s probably better to focus on the great cities rather than places more known for scenery and outdoor activities. If your budget is generous then my top choice would be London, Paris, and Amsterdam. You could fly into any of those and then visit the others by high-speed train. The train that connects London to Paris and Amsterdam is called the Eurostar, and the earlier you buy your tickets the cheaper they will be. Paris and Amsterdam are linked by normal high-speed trains, which are also cheapest when you buy early. Speaking of that, your dates are prime travel dates over the Christmas holidays so the airfares will be kind of expensive and they will only go up from here. In other words, buy as soon as you can.
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.
Most hotels these days include at least a small refrigerator, and some even include a full kitchen and stove. This is great because it allows you to shop locally for some fresh food options. Search online for nearby farmer’s markets or grocery stores and see if you can pick up some local meats or fresh veggies to have in your room. This is more likely to be an option in the warmer months.
You still get warm ocean breezes and 70-degree temperatures, plus the Hawaiian islands go all out for the holidays. Locals host potlatch-style parties where the Christmas goose is replaced by a luau pig, and the resorts deck themselves out like tropical North Poles, including a massive tree-lighting ceremony at the Outrigger on Oahu and tree-decorating contests at Mauna Kea on the Big Island. Residents there climb to the top of the 13,000-foot-tall volcano, shovel snow into their trucks and speed back down to build snowmen in their yards before it melts.

A charming, historic city to visit any time of year, Edinburgh is especially festive during December. Walking through its cobblestone streets takes you back to medieval days when sheep, cattle, and grain were sold in what is now the center of the city. Today, the Royal Mile includes shops, cafes, and museums. Edinburgh Castle, a must for first-time visitors, dates to the 12th century, with its dramatic silhouette overlooking the city. For those seeking holiday celebrations, the Royal Botanic Garden is decorated with lights, music, and illuminated trees. European-style Christmas markets pop up at Princes Street Gardens and George Street, offering traditional crafts, gifts, food, and warming drinks, most welcome during chilly December. The annual Hogmanay celebration welcomes the New Year with fireworks, food, and festivities. Don’t miss the delicious and ubiquitous fish chowder called “Cullen skink,” and be sure to try haggis, served with “neeps and tatties” — mashed turnips and potatoes. Buttery shortbread and whisky from the country’s more than 100 distilleries are also Scottish specialties. A stay at the elegant and historic Balmoral Hotel will enhance any visit to Edinburgh, and while you’re there, you’ll notice that Scottish actor Sean Connery was a guest, as was J. K. Rowling who finished the last Harry Potter book in one of its suites.
Similar to so many on this list, Cape Town begins its busy season in the second half of December, so November is ideal in that the weather is nearly perfect and you don't have to worry about high-season crowds or prices. This is a city that has things available at almost any price level. Many of the hotels cater to the 4-star resort crowd, but there are also plenty of hostels and cheap hotels so backpacker-types should be able to get by on a low budget.
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.
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
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.
Mother Nature is the gift that keeps on giving this December. In the snowy Swedish village of Jukkasjärvi day-long darkness provides the backdrop for the most magical light show on earth, the swirling aurora borealis, while opportunities to hang out with Rudolf and co. or try husky sledding, snowmobiling and cross-country skiing abound. Swap the blanket of white for a kaleidoscope of colour in the Amazon rainforest. Now is the ideal time to spot dazzling birdlife, especially the rainbow-feathered macaws that come to munch on the mineral-rich clay in Peru’s Tambopata National Reserve.
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
Interestingly, December though February do get a bit cool in Cairo, so it's not a great winter break, but in November it's still pleasantly warm and bone-dry so you can enjoy the outdoors for long periods of time. If you don't mind staying in a locally-owned hotel you can save a lot of money and see some old-world charm at the same time. Reservations in advance aren't necessary, but it's best to book your first couple of days just to avoid all the confusion once you arrive.
In colder weather it’s probably better to focus on the great cities rather than places more known for scenery and outdoor activities. If your budget is generous then my top choice would be London, Paris, and Amsterdam. You could fly into any of those and then visit the others by high-speed train. The train that connects London to Paris and Amsterdam is called the Eurostar, and the earlier you buy your tickets the cheaper they will be. Paris and Amsterdam are linked by normal high-speed trains, which are also cheapest when you buy early. Speaking of that, your dates are prime travel dates over the Christmas holidays so the airfares will be kind of expensive and they will only go up from here. In other words, buy as soon as you can.

“Winter in Eastern Canada” might sound more like a 19th-century prison sentence than it does a pleasant vacation, but Quebec City does the cold better than anywhere in North America. Blanketed in snow, QC looks like the world’s most elaborately constructed Christmas village. The cobblestone streets in Old Quebec densely packed with storefronts beckoning you to come in for hot food and baked goods, and boisterous bars overflow with a cacophony of Quebecoise. In December the streets are draped with Christmas wreaths and populated with carolers, plus there’s an authentic German Christmas market -- a true novelty in a city so overwhelmingly French.


You might also consider Malaysia and perhaps a stop in Singapore. Malaysia is actually more modern than Thailand so everything is easy and reliable. They have cheap VIP buses that are very comfortable. Penang in the north is really nice and also interesting. Kuala Lumpur is a modern and pleasant big city. A bit south of that is the colonial town of Malacca, which is also very nice and worth a look. Going south from there you can reach Singapore in a few hours, and that is an amazing city, although accommodation there is expensive.
Sri Lanka could also be great, and it’s very different. In fact, you might even consider a trip to India itself, which is obviously similar to Sri Lanka. But Sri Lanka is far easier to do in about 12 days, with most of your time spent in the mountains and a bit along the southern coast. Colombo is mainly just good for flying in and getting your bearings. Sri Lanka is also a bit more expensive than Vietnam, but both are great value. And again, you could instead go to Kerala and Goa in India on a short trip, although those are more about relaxation than culture. Let me know if you have any other questions, and I hope this helps. -Roger

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.

If you book a resort hotel from home you'll probably think Goa hotel prices are much higher than you were expecting, but if you book a family-run place once you arrive you'll still find fantastic bargains. It's probably wise to book a few nights online before you get to India, because it can be incredibly confusing at first. After that you might be able to find a similar place for half the price by just checking around the same area.


Another option would be Cambodia and/or Vietnam. The town of Siem Reap, which is just next to the Angkor Wat Temples is the real highlight. Phnom Penh is worth a quick look, but not on a shorter trip. Vietnam itself is a wonderful and gorgeous country, and you can see a lot of the highlights in 10 days or so. It’s also very cheap, even around Christmas. You could fly into Hanoi and then go see Ha Long Bay, and then take a train down to Hoi An. After that you could go to Nha Trang for the best beach experience or the hilltown of Sapa. The city of Ho Chi Minh City is quite crowded and you might not like it for more than a day or two.
For traditional holiday atmosphere, think about Rome or Vienna, with Christmas markets, nativity scenes, and decorated cathedrals. In Edinburgh, they know how to welcome the new year with several days of celebrations culminating in New Year’s Eve. For travelers seeking a wintery destination, Tromso in Norway has skiing, reindeer, and a chance to see the Northern Lights. Bundle up for a dogsled tour or join a whale watching excursion.
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.
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.
For those looking for an even calmer slice of paradise without all the holiday festivities, try Waimei on Kauai’s southwestern shore, which offers calm waters and sandy beaches that are especially attractive in the early winter months. Get away from all the gloomy weather of the East Coast by trying out a Waimea vacation rental—it’ll definitely make for makes the perfect base to explore all Kauai has to offer.
A charming, historic city to visit any time of year, Edinburgh is especially festive during December. Walking through its cobblestone streets takes you back to medieval days when sheep, cattle, and grain were sold in what is now the center of the city. Today, the Royal Mile includes shops, cafes, and museums. Edinburgh Castle, a must for first-time visitors, dates to the 12th century, with its dramatic silhouette overlooking the city. For those seeking holiday celebrations, the Royal Botanic Garden is decorated with lights, music, and illuminated trees. European-style Christmas markets pop up at Princes Street Gardens and George Street, offering traditional crafts, gifts, food, and warming drinks, most welcome during chilly December. The annual Hogmanay celebration welcomes the New Year with fireworks, food, and festivities. Don’t miss the delicious and ubiquitous fish chowder called “Cullen skink,” and be sure to try haggis, served with “neeps and tatties” — mashed turnips and potatoes. Buttery shortbread and whisky from the country’s more than 100 distilleries are also Scottish specialties. A stay at the elegant and historic Balmoral Hotel will enhance any visit to Edinburgh, and while you’re there, you’ll notice that Scottish actor Sean Connery was a guest, as was J. K. Rowling who finished the last Harry Potter book in one of its suites.
Those wanting to hike to Machu Picchu will also find this to be an ideal month, since getting in a group will be easy even without much advance notice. The train to Machu Picchu is expensive year round, and reservations should be easier to get the day before this time of the year. Hotels are always cheap in Cusco so you can afford to get something nicer than you are used to this month.
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If you do want to go to Thailand then Bangkok is the obvious starting point and it’s a wonderful city. You also want to visit Ayutthaya, which you can do on a day trip but it’s better to stay a few days. Chiang Mai is the highlight of the north, partly because it’s insanely cheap and the weather is a bit cooler than Bangkok. Luang Prabang is another town not to miss and it’s fun for at least a few days. Don’t bother spending much time in Vientiane though.
The secret to a pleasurable European vacation in November? Go south. While cities like London, Paris, and Berlin feel the winter chill this time of year, Lisbon has the good fortune of a subtropical Mediterranean climate—which means temperatures are in the mid 60s. Book a room at the landmark Tivoli Lisboa in the center of the city. The luxury property sits on Avenida da Liberdade, a bustling boulevard that’s akin to New York’s Fifth Avenue. Ask the hotel to arrange a “Vintage Lisbon” walking tour and explore the city’s rich art and architecture scene.
If you are looking for beach weather in December then most of your list won’t work, and several of them are only on rivers. Starting from Kolkata you have many good choices that are much closer to you than anywhere in Europe or the Canary Islands, or the Caribbean for that matter. In fact, I’m a bit confused by your list because there are so many different types of places on it, many that aren’t warm or on beaches.
Plus, Colorado is home to the world-renowned Breckinridge, a historic town at the base of the Rocky Mountains’ Tenmile Range that’s well-known for its ski resort, year-round alpine activities, and Gold Rush history. You’ll also find tons of shops, galleries, and restaurants housed inside colorfully-painted Victorian buildings, along with four whole mountain peaks that provide 2,358 acres of enough variety to suit even the most seasoned of skiers, boarders, or even snow-shoers. It’s also important to mention that last season, the Summit County municipality saw 447 inches of snow. Lifts open up in November, so what are you waiting for?!
Since you mention the temperature in Fahrenheit, I’ll assume you are in the United States. You might have to go to the Southern Hemisphere to reliably get 84F or higher, but you can get over 80F in most of the Caribbean. You’ll get low 80s in Hawaii in early December as well. Fortunately, neither of those places get too crowded until just before Christmas, so either should work.
Those wanting to hike to Machu Picchu will also find this to be an ideal month, since getting in a group will be easy even without much advance notice. The train to Machu Picchu is expensive year round, and reservations should be easier to get the day before this time of the year. Hotels are always cheap in Cusco so you can afford to get something nicer than you are used to this month.
Yes, Australia is pretty expensive by most standards, although it shouldn’t seem too bad since you are coming from Singapore. Hotels in Australia are pretty expensive no matter where you go, although quite a bargain compared to the same thing in Singapore. Restaurants in Australia will seem quite expensive compared to the hawker centers, but not bad compared to Singapore’s sit-down restaurants.
If you are looking for an island that is moderately priced in late November I would probably head to Thailand. The rainy season typically ends in the middle of November in Phuket and Ko Samui and the other popular islands, although you might still get a few quick storms in late November. One nice thing is the crowds don’t start coming until mid December so you have a huge selection of hotels at really good prices.
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.

My girlfriend and I want to plan a trip anywhere from December 24th ish to January 6th ish mainly for my bday and new years to get away from south Florida! Last year we went to Colorado which was awesome but I’m not sure we want another cold vacation though it’s not out of the question! Saw your blog and Bali looks awesome but very expensive flights! Been to Costa Rica which was pretty cool and always kinda wanted to see machu pichu too. Even maybe somewhere in Europe or the Mediterranean would be great but have to keep the budget down too as we don’t have a ton of money to blow! Any insight or recommendations would be greatly appreciated! Thank you!

Regarding Thailand, I’m not familiar with any islands that are beautiful and not touristy. Phuket has beaches all over the island and many of them are isolated so the only guests are those staying at the resort in front of them. If you search other travel sites, including travelfish.org, which I think is the best site for southeast Asia and it’s run by a friend of mine, you can find more information about more obscure Thai islands. One challenge could be that you might have to take two or three total flights and then a ferry ride to reach them.


If you ask at a hotel in India about getting train tickets, they almost certainly know a way of getting them for you. They share in the profits of the commission, so they will usually find a way. However, perhaps in Goa it is less common because the train stations are a long way from the beaches so it could be a 3-hour return trip to the station instead of a 20-minute trip in the cities.
The Brazilian currency has been falling in recent years, and if this trend continues then Rio de Janeiro will be squarely back into the bargain category. It's certainly not as cheap as it used to be, but for the amazing beaches and scenery it's easily worth it as long as you plan well and stay safe. In fact, Rio has some of the best beaches in November anywhere in the world, and a vibrant city right next to them.
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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