Resolve – My number one asset to staying on track was my resolve. I made my mind up before we left that I would not give in when tempted and that I would be entirely aloof for donuts, desserts, fries, and other favorite treats. I just kept reminding myself that I could enjoy those foods again perhaps on our next weekend getaway or at the end of our vacation if I chose to have a cheat day. Otherwise, they would be dead to me because I didn’t want my kids feeling guilty eating treats in front of me. I don’t want them ever to relate being good or bad based on what they ate so again; I had to have the mindset that it wasn’t a big deal.
If you are very sensitive to humidity (I normally am, to be honest) then you’ll find more pleasant weather pretty much anywhere else in Southeast Asia in December. It can actually be cool at night in places like Chiang Mai that month. On the other hand, I LOVE Bali and I’ll probably spend all of next February there, which is still in the wet season. I’d still seriously think about Bali if I were you.

It would probably be a bit more expensive, but another idea that could be great would be to fly to San Juan, Puerto Rico, and rent an apartment for two weeks. It’s a wonderful place that is family friendly, and rental apartments can be good deals. It’s obviously peak season there as well so nothing will be cheap. But the weather will be fantastic and the beaches are great, even in and near the city. I hope this helps. Let me know if you have any other questions.
Hi Roger, I plan on being in boracay on Nov 6th and am just concerened about the weather. Is the start of Nov too close to the end of the monsoon season ? I don’t mind a bit of rain but ideally want to be able to spend a few hours on the beach with sunshine per day. Looking at pics it seems to be mostly clouded over all the time. Do you get sunny clear skies around that time ? I just can’t seem to get a clear answer online. Any advise would be much appreciated
Located just 90 minutes from New York City, the quaint Caribbean island is home to fantastic beaches—like the famed Horseshoe Bay and Elbow Beach—plus a unique style all its own. A balanced mix of charming British heritage and laid-back tropical vibes, Bermuda has, in recent years, become a hotspot over the holidays. The weather is typically temperate (expect temperatures in the 70s) which makes it a perfect destination for golf-lovers, families, and anyone looking for a quick weekend escape.
From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. 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.

Aside from that, this is a bit tricky because you obviously want to avoid longer flights for a short trip and especially with an infant. And some of the closer options are not close to a major airport, so they are still hard to reach in half a day or so. I think if you want to go farther than Goa, it’s probably best to look for other options in Thailand. As you know from previous visits, Thailand really has tourism figured out and it feels safe and well organized there. Cambodia and Vietnam also have beaches, but none that I’d recommend for a short trip. It’s the same with the Philippines, and the flights start getting longer. Phuket is the largest Thai island by far and it’s got over a dozen different beach areas and towns to choose from. Patong Beach is the main beach town and I wouldn’t recommend it for a family, but Kata and Karon beaches are just south of that, and they are nicely family oriented. Phuket also has a large airport, so getting there quickly is pretty easy compared to other beaches and islands in the area. Phuket’s beaches are also very nice. I wish I had more suggestions for you. Let me know if you have any other questions. -Roger


If I had more information about destinations in East Africa that would qualify I would love to include them. But unfortunately, it’s one of the few regions I haven’t been to myself, and according to every source I hear, very few foreigners are visiting as well. I know many (especially wealthy) people do the safaris in that region, or they walk up Kilimanjaro, but outside that it still sounds like there is almost no tourist infrastructure or even a backpacker scene. If you know things to be different, please let me know because I’m very open to it. -Roger


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.
Costa Rica is kind of the Thailand of Latin America in that they have great tourist infrastructure and it’s the easiest place to get around. They also have a lot to offer with the beaches on both coasts and many natural sights and activities, plus of course the Arenal volcano, which is a really nice area. San Jose is best as a place to just pass through on your way somewhere else.
On my own trip I spent 3 nights on the North Island after leaving Auckland, and then 4 nights on the South Island. The South Island is more scenic and interesting, and much less crowded, so I would have liked to have stayed another 2 or 3 nights if I had the time. So I’d recommend 3 or 4 nights on the North Island and 5 to 7 nights on the South Island. With smaller towns and smaller crowds on the South Island, that is the better place for star gazing, though most of the North Island is fairly empty as well. It’s an amazing place and I’m sure you’ll love it. Have a great trip. -Roger
As December begins in the Caribbean, the hurricane season is officially over and the weather is pretty much perfect by any standard. Punta Cana is the Dominican Republic's most popular resort areas, especially for those who aren't particularly interested in absorbing the local culture. This is a resort area with wonderful beaches and not much history.
That definitely helps! Though I think I was quite unclear in the first place. Being in the same region is definitely not a constraint. We’ve been considering Africa as well, for example! Also, a couple of days of beach time is also sort of desirable, and we’re not really into visiting cities as such. Ideally, we wish to have some time to spend on beaches/resorts/hotels along with some time in a place like a safari or something.
I think the best place for what you want is Thailand. You can choose from Phuket or Ko Samui or one of many other islands, and they all have nice beaches and good nightlife at a very reasonable price. There are other places in Asia that have warm December weather, but Thailand’s tourist infrastructure is better than the others so it’s just much easier to get around and do what you want. Let me know if you have any other questions. -Roger
We are looking to explore warm Central American destinations safe for kids and affordable in price. We love beaches. Not in the typical sun-bathing type of way, but rather appreciating the raw beauty of the nature. We also like to eat out and having activities for the kids and as a family would be excellent. Could you suggest a destination that fits the bill? Central America appeals to me but open to other suggestions you may find worth mentioning.
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.
If you are more interested in nature and adventure than culture, then the top choice would be Costa Rica. The country has many beautiful national parks and it’s filled with things like zip-lining and canopy tours, just to name a few things. There are also volcanoes and surfing beaches and much more, plus a very good backpacker infrastructure of cheaper hotels and hostels.
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.
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 with most on this list, hotels get very full and more expensive just before the Christmas holidays, so it's better to come early in the month if possible. That way you'll have your pick of places at some surprisingly good room rates, even at some high-end places on the famous beaches. If you are coming during Christmas then book a hotel NOW because they'll be full and will keep getting more expensive the longer you wait.
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.
From Atlanta, the places that come to mind with the theme of “nature” would be Costa Rica and Belize. Costa Rica is probably the better choice, as it famously has around a third of its land as natural parks. Much of it is jungle, and they have all sorts of activities including zip lining, but also canopy tours and much more. There is also the Arenal volcano there, which is really nice and has some fun hot springs around it. They also have beaches, of course, but there is plenty in the interior of the island to keep you busy. If you know a bit of Spanish, it helps, but most other visitors know little or none.
I’ll be happy to give you some suggestions, but it would really help to know your starting point and approximate budget. At this moment I am writing this reply from Cancun, which could be perfect if you are in or near the US, but if you are in another part of the world there will likely be better choices. Although thinking about it, even if you are in Europe, a place like Cancun might still be best. Let me know and I’ll give you my best answer and an alternative or two. -Roger
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 an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.
We’re a couple and are planning a 5/6 nights trip [around Christmas] from India to some place that is slightly reasonable and wonderful, of course! What we’ve been considering till now is Maldives or Cambodia or Thailand. Can you suggest anything around these or even completely different from these? The reason why we haven’t been able to finalize till now is that we’re trying to find a destination other than beaches, which isn’t as easy as it appeared!
The last one is a 10 day trip for spring break 2018 most likely to be from March 9th to March 18. I’m thinking Europe but I don’t want to stay only in one country. I have so many options that I need someone to shorten the list in a way that it will work out. I want to go to Amsterdam, Rome,Venice,London,Barcelona,Zurich,Madeira,Dublin, and Madrid. (Amsterdam & Barcelona are a must).
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.

2. We read lots of things that leads us to believe that Tanzania is great this time of year. We are choosing 7 day safari with time on back end to rest for 3 days at hotel. Anyway, my question to you is ANY tips or must do’s on a safaris. We are personalizing the trip to some extent because we are a group of 7 and are not joined by other families. Also, any DONT DO’s on a safari? Any advice on booking our flights? Websites?
Thank you for the kind words. I know what you mean about the image of Thailand and Bali, particularly among Australians. On one hand you could go to either of those places and easily avoid the most notorious party neighborhoods, but it’s probably easier to head somewhere else since both of those places are so crowded that time of year anyway. I do have a few suggestions, which I’ll describe briefly and then if you want more details about any that appeal to you I can do that in a follow up comment.
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.
It's been said Jackson Hole is where Aspen meets Palm Springs. Ski season, however, really starts in mid-December. There's world-class—not to mention some of the most vertiginous—skiing in the continental U.S. Plus, miles and miles of trails and nature to enjoy less vertically trekking through Grand Teton National Park and Yellowstone National Park. To put much of this at your fingertips, the Four Seasons Jackson Hole has a ski concierge and is a ski-in/ski-out property.
A visit to Vienna in December might be a holiday experience of a lifetime. From the festively adorned palaces, magical Christmas markets, classical concerts, and choirs to the cozy cafes and restaurants, the surreal atmosphere seems like a Hollywood movie. With nearly a dozen Christmas markets to choose from, the one in front of City Hall is notable for its giant tree, ice skating rink, carousel, and reindeer train. At another in Freyung Square, you’ll find delicious mulled wine, gingerbread, roasted chestnuts, and a variety of regional snacks in addition to jewelry, handmade toys, candles, and more. The market at Spittelberg, set amidst lovely townhouses and narrow streets filled with bars, restaurants, and galleries, is a wonderful place to sip champagne and browse the many shops. Set in front of the world famous baroque residence, the Christmas Village at Belvedere Palace should not be missed. Book a Christmas concert at the renowned Kursalon where Johann Strauss was the concertmaster or enjoy a recital at one of the many distinguished churches through Vienna. You can even take a walk or a “hop on, hop off” bus to enjoy the Christmas displays. No winter night is complete without a stop at a sausage stand for a succulent bratwurst served with mustard, horseradish, and a classic bun. In the heart of the city, the magnificent Hotel Grand Ferdinand would be the perfect home base for exploring Vienna.
Reading through your wonderful comments- looking for Xmas for 6 people that have travelled extensively. Caribbean now is “out” and still fear zika since my kids are in their 30s- or do you think zika is a scare of the past? Uruguay has been on our radar and so i thought it interesting that you had a recent comment. Galapagos is filled. Maldives? Do you think Cuba is still an option after Irma and with current US relations? Thanks
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.
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