If you’re a bit more on the timid side, you can always use Yelp and TripAdvisor to get good insights on places people have visited. As a disclaimer, some of the ratings may not be accurate on these sites, so make sure you go through and read some of the more recent reviews that people have written. We did this for a few of the places we visited and had no issues.
The eleventh month of each year brings nice fall foliage, a nice pre-holiday calm, and tons of things to give thanks for—especially when it comes to traveling. From the Big Apple to the Sunshine State and all the way to the Pacific Coast, it’s easy to rest and relax before the seasonal hoopla by escaping into the grey blue skies and cooler temperatures of late fall by attending a star-studded annual parade, adventuring into the wonderful world of Disney with the kids, or even getting away to a tropical paradise to experience a warmer weather vacation getaway.

When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.

In her dynamite cookbook “Martha Stewart’s Vegetables,” the queen of domesticity shows how acorn squash can be a canvas for a variety of flavors. Roasted with sesame seeds and cumin, the squash takes on the warmth of the Mediterranean. Tossed with bacon, maple syrup and a touch of cayenne, it echoes the comfort of the breakfast table. And paired with orange peel, sage leaves and a touch of grated Parmigiano offers the perfect balance to rich gravy and herbed stuffing.

Warm weather, Caribbean beaches, and fascinating history beckon visitors to this coastal city during December. Once a 16th-century Spanish port, Old Town Cartagena, surrounded by ancient stone walls, is a UNESCO World Heritage site. Visitors strolling through its streets will see original Spanish Colonial architecture among new restaurants, restored homes, and boutique inns. From street food to upscale restaurants, Cartagena offers the best in local seafood, meat, and fresh fruits. In December, the city becomes a festival of lights, with nativity scenes, decorations, and holiday celebrations culminating with New Year’s Eve fireworks. Holiday shoppers will want to take home gifts of colorful handcrafts sold at markets throughout the city, with special Christmas markets arriving in December. Colombia supplies nearly 90 percent of the world’s emeralds, and a quality gem from a reliable source would make a memorable keepsake. Nearby Rafael Nunez International Airport makes arriving by air quite convenient, and visitors will find a range of lodging in and around Cartagena. For a luxurious vacation, the new Conrad Cartagena offers four pools, a private beach club, a golf course, seven restaurants, tennis courts, a spa, and stunning ocean views from every room.

Thank you for the insightful details about South America and the others! Peru, Costa rica sound ideal! Always wanted to work at a sustainable place is Costa Reecs. However, I am also quite interested to know what Brazil , rather the different parts of Brazil are like, since it is so huge would be interesting to visit during the same time of the year.. Since I love and play Capoeira too, I’m pretty tempted to visit Brazil and draw inspiration. 🙂 And what is Colombia like?
Blisteringly hot in summer, Tokyo is a breeze in the cooler months. Fight the dizzying jet lag and head out for the world's best sushi or ramen, shop in the city's amazing department stores, and visit the parks surrounding the Imperial Palace in the center of the city. Escape the crowds somewhat by heading to Yanaka Ginza, which retains a bit of old Tokyo and has plenty of places to eat and shop. Do make time for a side trip to Hakone, where you can visit a Shinto shrine and see magnificent Mount Fuji on a clear day.
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.
For anyone considering a multi-destination South American trip in November, Santiago should definitely be looked at. The daytime temperatures should be pleasant and warm, and it's bone-dry all summer, so it's a great combination. Hotels in Santiago don't have their peak price season until New Year's, so in November you'll easily be able to find a very good rate at one of the nicer places.
Since you’ve been to several of the top places in Asia already, and you love it, I think Bali might be your best bet. As I’ve written many times recently, I feel that the main tourist area of Kuta/Legian/Seminyak is just too crowded and overdeveloped to recommend, although it is interesting for a couple days and some nightlife. The arts and crafts town of Ubud is still nice, although also a bit crowded, but it’s not anything like a city so I still think you’d enjoy it.

As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.
In Rome, the Coliseum and Ancient Rome are outdoors, but the city also doesn’t get as cold as the others so most likely you’ll be fine if you bundle up a bit. In Venice, they often have those floods during December, but they come and go every 6 hours so even if you get unlucky you’ll still be able to get around half the day, and it’s a small city anyway.

As far as finding work on the road, the only decent-paying job that is fairly easy to get that I’m aware of is teaching English, but I think those gigs tend to last at least a few months. Right now Thailand is trying to get rid of any foreigners who are working in hotels and bars without permits, so Cambodia might be better at the moment. I’m one of the thousands of people who work online while traveling, and it seems much easier to make a decent living that way compared to working in hostels and such. Good luck with whatever you decide, and maybe I’ll see you on the road at some point. -Roger

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

With a vibrant downtown, great restaurants, culture, and a recent multi-million renovation to the Ritz Carlton, Naples, one of the areas most luxurious hotels, December is when the town really starts to get into gear. You can spend your time on the miles of gorgeous Gulf Coast white sand beaches, take an Everglades Safari, or head to the Artis-Naples which hosts world class dance, theatre, music, and comedy. And that is to say nothing of the five-star shopping.


The fastest high-speed trains between those cities only take 2.5 hours, although most departures are closer to 3 hours. Definitely take the train and also buy the ticket as far in advance as possible for the lowest fare. Not only is it FAR quicker than flying (and of course the coach), but it’s far more comfortable and more enjoyable. This is a link to the official Spanish rail site. The scenery isn’t all that special, but it’s still interesting. Have a fantastic trip. -Roger
If you really want to see the city up close, visit in November or December, when the crowds have dispersed. Hotel prices are comparatively low, and gondoliers are more appreciative of customers. And once you have your fill of religious art, head for the Peggy Guggenheim museum, which displays 20th-century American and European art in a home and garden setting. Note: October through January is the time of acqua alta, when Venice may flood. Usually it's not severe, and the city puts up wooden walkways for visitors and residents to traverse the water.
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!
Preheat oven to 425 degrees. Line a rimmed baking pan with a sheet of parchment paper. In a medium bowl, toss the green beans, garlic and olive oil together until completely coated. Then, spread the coated green beans on the lined pan in a single layer without crowding. Season with salt and pepper, then roast in the pre-heated oven for 15 minutes. Remove from oven once during this time to turn the beans so they cook evenly. When finished roasting, remove from oven and place beans on serving tray. Before serving, drizzle with extra virgin olive oil and sprinkle with grated Parmesan cheese. This makes a great recipe for Thanksgiving dinner sides.
The Canary Islands are always an option and the weather in November is pretty decent. I spent almost a month on Tenerife a couple years ago and I thought the nightlife was mostly pretty cheesy, although at least the drinks are cheap. I think in summer the nightlife there might be good, but in the other months I think it’s pretty quiet because it’s mostly older visitors from northern Europe.
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.

The “city that never sleeps” is a delight in December, even if the weather makes it necessary to bundle up a bit. For holiday spirit and things to do any time of year, New York City is a top destination. Broadway and off-Broadway shows are exceptional entertainment, and the Radio City Music Hall Christmas Spectacular with the famous Rockettes is a perfect holiday event. The New York City Ballet at Lincoln Center presents the classic "Nutcracker," a seasonal tradition. At the New York Botanical Garden, the toy train will wind its way through a miniature Lower Manhattan for the amusement of kids as well as nostalgic adults who may have once had their own train sets. The dazzling Rockefeller Center Christmas Tree, New York City’s centerpiece each year with nearly 50,000 lights, will once again overlook the famed ice skating rink and golden Prometheus statue. Window shopping takes on new meaning during December when department stores along Fifth Avenue entertain passers-by with intricate decorations and displays. Holiday markets at Bryant Park, Columbus Circle, and Union Square also invite browsing and shopping along with warm drinks and food. For a convenient stay, the Renaissance New York Midtown Hotel offers spectacular views and Versa, a year-round rooftop restaurant and bar. Or enjoy the Innside by Melia New York in the trendy Chelsea area with its newly opened seafood-focused dining spot, The Wilson.
I like your comment about how “rainy seasons” are almost always overstated. I totally agree based on my own experiences and research, although there are a few places where they should be taken more seriously than others. On my most recent December trip to Bali (2.5 years ago, I think), I spent 30 days there and the rain only became a problem that one time I mentioned. It was just an insane cloudburst while taking a minibus from Kuta to Ubud, and in the end it’s actually probably my best Bali story. Aside from that, it’s very humid during Bali’s wet season, but even that really didn’t slow me down. The thing is, in Bali you are usually on or near the beach or a hotel pool (feeling the breeze) or in your air-conditioned room. Or you might be touring around to see temples and rice terraces and whatnot, and everything is outdoors and beautiful. When it does rain it’s usually over in 15 minutes, but often the rain comes over night. That kind of humidity can be a killer when visiting a city, but for me it’s a small issue on a tropical island like Bali.
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.
Much of Mexico is ideal in December, after the rainy season has ended; if you go early in the month, you’ll avoid the peak holiday-season rates that kick in around December 18. On the Pacific coast, the landscapes are still ultra-tropical green, and the ocean is bathtub-warm (80s), with exceptional clarity for scuba diving and snorkeling. Mexico City is a smart place to spend the holidays, when the locals have headed to the beach and you’ll find much less traffic in this famously congested city. (Do keep in mind, though, that some of the more sought-after restaurants and galleries will be closed.)
This year I’ve based myself in Miami, USA, primarily so I can visit many places in the Caribbean that I hadn’t been to before. I just got back from a week in Jamaica and soon I’m going to Puerto Rico, Dominican Republic, Panama, and Colombia, as mentioned. But in December I’m hitting the road again and I’ll be in Asia for the winter and probably in London for much of 2016. Sorry I don’t have more specific information to help you plan your trip, but it sounds like you’ve got some really good choices already under consideration. And I’m sure you’ll have a great time. -Roger
That really depends on your starting point. Most of the cheapest places are in Asia, but the flight would be quite expensive if you are in North America or Europe. If you are in the US, your best bets for cheap places with good weather that time of year will be the non-resort towns of Mexico, or even the resort towns if your budget is a bit higher. Let me know your starting point and more about what you are looking for and I can give you a more complete answer. -Roger
Those who adore the holidays and don’t mind the cold (the average high is around 48 degrees) might consider an end-of-year trip across the pond. Arguably Europe’s most festive destination, December in London promises charming Christmas markets, show-stopping Christmas trees, and streets covered in twinkling lights. A number of posh hotels, like 45 Park Lane and The Dorchester even have Christmas-centric packages available to get you into the holiday spirit.

Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.

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