December is a fun time to be in Rajasthan (though a busy one—this is peak season). The weather is cooler—something to relish, as it means long explorations into the bazaars, wonderful walks around the forts, and a chance to explore the villages on foot without overheating. Evenings are spent wrapped in beautifully decorated Rajasthani shawls and blankets as you dine outside by firelight. The winter light is beautiful, particularly in the villages, making this an ideal time for any travelers with a passion for photography.
If this were last year I might have also suggested San Juan, Puerto Rico or Cartagena, but both of those have issues at the moment. If for some reason you don’t like what you see in Costa Rica, there are also some really nice resorts in Panama, especially in the San Blas Islands area. Aside from those you’d probably have to fly longer than you prefer. I hope this helps. -Roger
In spite of its image of being blazing hot all the time, December in Cairo can actually be on the cool side, at least in the evenings. This is great though because almost all the important sights are outdoors and requite a lot of walking between them. For 9 months of the year it can get very hot doing that, so these few cooler months are ideal for visiting the famous sights.
Cambodia could work because Siem Reap is inland and the amazing Angkor Wat temples are worth a full day or two, and the town of Siem Reap itself is quite nice. You could actually combine a couple days in Siem Reap with a few days in Bangkok, and take a (cheap) luxury bus between the two. Bangkok is a really fascinating city with a lot to see, plus it’s a great transport hub. The other main non-beach option in Thailand is the city of Chiang Mai, which is wonderfully inexpensive with quite a bit to see. It’s even a bit cool during December, so that might be a nice change of pace from India. Many people are also going to Myanmar these days, although I haven’t been yet so it’s hard for me to recommend it. I’d say if you combined 2 or even 3 of these places you could have a very interesting holiday.

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.
If you are referring to days trips and that sort of thing, it will be much cheaper if you book once you get there. In Vietnam in particular it’s amazing how cheap tours can be if you book them through your hotel. I once did a 6-hour bus tour to Mỹ Sơn, which is near Hoi An, and I think I paid about US$6. It even included a boat ride and a basic lunch. That same day tour online would probably cost US$30 because the booking company takes a share and there is very little competition.
I think Spain is probably your best bet, and you can probably get there on a reasonably priced flight with a change in Dubai or Abu Dhabi. The winter weather is decent and the big cities are always packed with locals rather than so many tourists. Barcelona is probably more fun than Madrid, though both are big cities with a lot to see and notoriously good nightlife. If you get a cheap enough flight I don’t think you need to do a package. It’s pretty easy to get around Spain’s big cities just on English, as long as you do a bit of research. In 5 days you could spend 3 days in Barcelona and then 2 days in Madrid, or just 5 days in the Barcelona area. It’s a big city with plenty to see and some good day trips. You could also go to Valencia, which is also really fun and a short train ride away.
Yes I travelled a bit by train in southern India, I got lucky on my first few journeys with lack of people, then I hit some Indian holidays and it was hellish. I remember the trains being booked up for all the upgraded a/c and upper class carriages. One time even the Indians were fainting on the over packed carriage so you can imagine the heat for little old gringo me!
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.
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central.
As for flight connections, Barcelona and Madrid should have decent connections to Toronto and Delhi, while Casablanca (Morocco’s largest airport) probably does not. So Spain is the better choice by that standard. On the other hand, you can get to Morocco by ferry from Spain in a short time, so you could go to Spain and also visit Morocco for a day or two.
My first thought was Goa, which you say you’ve been to before, but maybe you don’t realize that there are about 20 different beach areas that are different from one another in terms of vibe and types of visitors? Personally, I found that Anjuna and Vagator were both kind of mellow but also busy enough and easy to meet other people. But if you don’t like those, there are many different beaches in the south, which I’ve heard are also great and draw different groups. It’s something to think about because it doesn’t get much cheaper than Goa for beaches anywhere in the world. -Roger
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.

From the Art Deco architecture to fabulous restaurants and nightlife, Miami is truly a city that appeals to every type of traveler. Art and culture lovers should plan a trip during Art Basel, which officially kicks off on December 6. The weeklong affair attracts celebrities, tastemakers, and bold-faced names, who come for the world-renowned art exhibitions, but stay for the swanky parties and events. Be sure to book a hotel well in advance, as prices skyrocket and availability becomes increasingly limited.

Depending on where you are going on vacation, you may have a measure of control over what you will be eating. For Keto dieters who are staying at a hotel and will be traveling from tourist spot to tourist spot, check with your hotel and see what kind of meal options their restaurant offers or whether there’s a continental breakfast. There may be fewer Keto-friendly options to choose from, but you will likely be able to find something to enjoy. Also, when out traveling, be sure to stop at grocery stores and purchase some Keto-friendly snacks that travel well, such as cured meats or cheeses, which can help keep you from overindulging.
From exquisitely decorated storefronts to the amazing Rockettes Christmas show at Radio City Music Hall, New York City attracts thousands of tourists every December. Visit the Big Apple during the holidays! It’s a sight to behold. We recommend visiting Rockefeller Center to go ice skating, go shopping at new pop-up shops or just enjoy a cup of hot chocolate at Serendipity 3.
I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -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.
Take Meal Times in Stride – Although I had intentions of planning keto/low carb meals by researching restaurants beforehand, especially at Disney, that never happened. Did I mention I have four kids? Yea, I don’t have a lot of downtime. Even so, I never had any problem finding foods that I could eat at restaurants. When we were out and about in Orlando, if we were thinking about eating at a restaurant that I hadn’t eaten at before, I looked their menu up online in the car before walking in. As long as they had a keto/low carb option, it was a go. I wasn’t picky. In fact, I ate either a bunless burger or bunless grilled chicken club almost every day at Disney or Universal. When my kids wanted to order pizza one night at our condo, I ate the toppings off with a fork. When they wanted Mexican food, I enjoyed Chicken Fajitas on a bed of lettuce. Whatever my family wanted, I found a way to make it work, and I never felt deprived. We typically ate breakfast at our condo, a late lunch (at Disney or Universal if it was a park day), then a late dinner out. By doing so, we also saved a great deal of money since eating inside the park can be so expensive. Since we stayed off site, the dining plan wasn’t an option.
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.
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!!
Your Munich plan sounds good. It can be fun to actually spend a full night in a town like Rothenburg ob der Tauber because it’s filled with day-trippers in the day and you almost have it to yourself at night. But it’s small enough that one night there would be enough. Nuremburg is quite a large city, and you might even stay there a night or two as well. I don’t know if I’ve ever heard of anyone saying they enjoy the cold and the rain, but if you do you’ll love it there. Fortunately, nowhere in the popular parts of Europe do they get extreme winters, and there is a good chance you won’t even see any snow in those cities. Most people are looking for the warmest places, which can be found in Portugal and Spain, but since that isn’t you I think your plan is good. Christmas is a big deal in some European cities such as Rome, but not a huge deal in others. Most businesses will be closed that day in nearly all countries, but of course hotels and many restaurants will be open. I hope this helps. Let me know if you have any other questions. -Roger

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.
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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