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 

Weirdly enough, Central America and South America aren’t really known as top “culture” destinations, as the colonial history has mostly wiped out the indigenous history in the larger places. There are Aztec, Maya, and Inca ruins and sights, but not really enough to build a whole trip around. I’d say the most interest of those would be the Inca culture of Peru, specifically around Machu Picchu and the valley around Cusco. Alternatively, visiting Argentina is pretty much like visiting Europe from a culture standpoint. It’s quite nice there and prices are low if you know about the blue market for currency, but otherwise it may not be what you are looking for.
While Cancun has become the king of the Mexican beach resort towns in the few decades since it was formed, it's only one of many, and all of them on both coasts have very nice weather in December. In fact, Cancun is probably the most expensive of them, so especially if you are coming from the west coast you are better off in Puerto Vallarta, Acapulco, or Los Cabos instead.
It’s going to be pretty cold in December all over Europe, although not quite so bad in the south, of course. As far as where to go, I’ll refer to our Europe 3-star traveler index, which lists every major city in Europe from cheapest to most expensive. The price is the typical daily expense per person for a couple traveling and staying in 3-star hotels. Once you scan through that list you should have some ideas.
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.
Thanks. I’ve been to other places in Egypt, but have yet to make it to Sharm el-Shiek. It’s hard to find places that are that inexpensive these days. Most of my best suggestions are in the article above. If your main priorities are beaches, sunshine, and nightlife, my favorites are Goa, India; Boracay Island, Philippines; and almost any of the Thai islands. Goa has many family-oriented beach towns, although some others are not so family oriented so you have to choose carefully there.
Assuming you might be in the US or Canada, my first hunch is Costa Rica, or Panama, which is a bit cheaper though not as well organized. Costa Rica has good surfing on its Pacific beaches, and there are very few all-inclusive resorts, which means that the restaurant scenes in resort areas are vibrant and interesting. Costa Rica also has limitless adventure opportunities, like zip-line tours and such, although they aren’t exactly cheap. Going inland you’ve got loads of national parks, as well as the famous volcano and its little spa town.

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.
Unlike most cities on South America's west coast, Buenos Aires has fairly consistent rainfall all year long, and you might see a bit of the wet stuff even during December. Still, the temperatures should be ideal for being outdoors, and this is really mostly an indoor city anyway, so when it does rain you'll be able to pop into a shop or museum or cafe and have a great time.
Let’s just say that November in Colorado is a truly exciting time of year. The city of Denver hosts several hot annual events, including Mile High Holidays, The Starz Film Festival, and the International Wine Festival. There’s also Denver Arts Week, which is a week-long celebration of the visual and performing arts held during the same month. What’s more is that snow aficionados looking to get an early start on winter sport fun should make resort reservations come November. The earlier you claim those spots, the cheaper the prices tend to be.
Italy should be at least a bit warmer than England this time of year, but not by all that much in a typical year. Also, if you only have about 9 days I think I’d try for no more than 3 or perhaps 4 total cities (Venice can be appreciated in about 24 hours if you are in a hurry). And of course, Paris and Amsterdam will both be quite chilly, so I think I’d save those for another trip. My recommendation would be to spend the whole trip in Italy so you aren’t so rushed. Do Rome for at least 3 nights and Florence for 2 or 3 nights, and then Venice for 1 or 2 nights. You could still have time to pop down to Sorrento for a couple nights to see Naples and Pompeii and whatnot.
It would be hard to beat Chiang Mai for its combination of great November weather and low prices. Even though it's officially the start of the high season for hotels, the beginning of the month is usually very slow anyway, so bargains are common. Hotels in Chiang Mai are among the best bargains in the entire world, so even if you do have to pay full price for a room it'll be cheaper than a dorm bed in most European cities.
Pretty much everywhere is going to be at or near capacity for those dates because half the world is on Christmas break. Between Australia and New Zealand, I think New Zealand would be far more interesting for 10 to 14 days. In Australia you pretty much have to spend a few days in Sydney, a few days in Melbourne, and a few days at the Great Barrier Reef, all of which require flights and will be very crowded over those weeks.
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
Overall, I’m declaring this vacation a great success! Not only did we have a wonderful time at the parks riding all the rides and enjoying the shows, I did not feel at all deprived or put upon food-wise, and not even once did I go hungry. All but one of our meals, including those at the hotel, were counter-service only establishments and I was able to find something filling and tasty for each meal. After this experience here are my recommendations for eating on vacation:
As for your Europe trip, I highly recommend spending 3 nights in any city you visit. If you change cities every day or every other day you’ll end up spending most of your holiday on trains or in airports rather than seeing the places you flew all that way to see. So if Amsterdam and Barcelona are musts, I would add exactly one other city if you’ve only got 9 days. Unfortunately it’s not on your list, but the best and easiest one to add between them is Paris. There is a train from Amsterdam to Paris in a bit over 3 hours, and another high-speed train to Barcelona from Paris in 6 hours 27 minutes with no changes. Paris is easily one of the most impressive European cities for tourists, but if you’ve been there before and don’t want to go again you can obviously choose something else.
Make like a Viking and soak those sore muscles in one of the many outdoor heated pools, some hidden away and others modern day gathering spots. The famed Blue Lagoon is Iceland’s best-known geothermal spa with temperatures of 98-104 degrees Fahrenheit. The lagoon’s waters are rich in minerals like silica and sulfur and are reputed to have healing powers for skin problems. There are saunas, lockers, showers, and towels available for a reasonable fee as well as restaurants and a lagoon side bar. Whale watching, though not prime season, is always an option in Iceland, as is dog sledding — on snow if available or dry land if not. Either way it is an amazing experience, and the meet and greet part allows you get up close to these beautiful dogs.  The younger crowd might enjoy the Iceland Airwaves Music Festival to be held in Reykjavik this Nov. 7-10 showcasing hundreds of acts, both famous and newcomers. Venues include bars, bookshops, theaters and concert halls.
Two other suggestions would be India or Sri Lanka. Except for a few beaches in Goa, neither of those attract the party crowd, and both are excellent for scenery and culture. India is cheaper as long as you minimize time in Mumbai and other big cities, but that is good advice for many reasons. Sri Lanka is a bit better organized, and on your budget it is good value and easily affordable. There are good beaches along the south coast of Sri Lanka, but India is probably better for beaches.
You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
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.
Hi Roger, What a great list! Answers to this question may not involve “great” weather. My 40+ yo boyfriend has never been outside the US (!) while I’ve traveled a bit (France, Spain, Italy, Greece, Iceland, Lebanon, E/W Canada, Mexico) and he’d rather go somewhere we both haven’t. We’re in Richmond VA and we’ll be travelling 11/22 – 26 this year. We love being outdoors and solo adventuring, don’t mind putting on rain jackets and lightly hiking/biking around old sites in 50-80 degree F weather; we enjoy delicious cuisine in hole-in-the-wall restaurants and staying in quirky hostels/Airbnb but also spending at least one day being tourons on a big red bus if available. Any ideas in eastern/western Europe? He’s really looking forward to going there. Thanks!
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.

Malaysia is a favorite of mine, although it’s not really known for beaches. Again, it really depends on what you are looking for. Kuala Lumpur is my favorite city in Asia because it’s got such a great mix of things and it’s also pretty affordable, but not everyone is looking for a big modern city. I’m happy to help with more recommendations if you let me know more about your goals. -Roger
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.
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