This is a tricky one. Pretty much every destination in the Tropics has its peak rates of the year during the weeks you have in mind. That said, there are still some fairly cheap destinations in the Caribbean, even at peak rates. However, since you live in South Florida and understandably don’t want to go someplace even hotter during the only semi cool time of the year, it sounds like you are ruling out most of the Tropics.
I totally agree about the solo traveling thing being down to luck in many cases. Right now I’m on a long trip around Europe again, and from one night to the next I might meet a bunch of interesting people, or be sitting there alone in a sea of locals with no interest in chatting with foreigners. At least in a place like Goa, everybody is on holiday, so I’ve had good luck meeting people.
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.

Hey Roger. My girlfriend and I are planning to go during Christmas for 13 days from San Diego, CA to South America mainly on the west side. We are not up for beaches but rather historical, adventurous, and scenic places. We are keen on Cusco (Peru) (Inca Trail), Quito (Ecuador), Costa Rica (Rain Forest), Bogota (Columbia). Please can you help us with your expert advice on which cities are a must for first timers to South America. We are not picky and simply want to have a fun time. Thank you for your time.

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.
But if you wanted more to explore the area near Singapore then Malaysia and Thailand are the obvious choices. The three most popular stops in Malaysia are Malacca, Kuala Lumpur, and George Town on the island of Penang. I quite like all of those so it’s hard to recommend one over another. I really like Kuala Lumpur and have spent quite a bit of time there, but honestly compared to Singapore it seems a bit untidy and old fashioned. In other words, if you are tired of a big and busy city like Singapore, then don’t plan much time in KL. Malacca and George Town are both smaller tourist cities with great food and interesting sights. There is frequent and cheap bus service from Singapore going through Malacca and onto KL. Then more buses from there to Penang and onto Bangkok.
Congratulations. In order to help you I’d have to know your starting point and also whether you are more interested in cities and culture or beaches and relaxation. November is a tricky month for beaches since it’s a very rainy month in most of the best and cheapest beach areas and islands in the Northern Hemisphere. But if you give me a bit more info I will try to help you the best I can. -Roger
Brazil, on the other hand, has a famous problem with petty crime in tourist areas so I wouldn’t recommend it for a woman and young child. Another to consider is Puerto Rico, which has a lot to offer including great weather, and it’s also more or less part of the US, so it’s fairly safe and well organized. Hotels in Puerto Rico are a bit expensive, but you should be able to get an apartment rental in the San Juan area (gorgeous, by the way) for a modest price if you are staying for more than a few days. Let me know if you have any other questions. -Roger
The sizzling summer days are in the past, and it’s time to enjoy your favorite outdoor activities whether they’re hiking, window shopping, al fresco dining, relaxing poolside, or strolling through Palm Springs — an adventure in itself. The Uptown Design District boasts home décor stores, boutiques, retro and resale shops, some specializing in the mid-century modern style that Palm Springs is known for. Further downtown, restaurants, small shops, and designer boutiques invite diners and shoppers. 
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.
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.
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

As for alternatives, you might have a look at my recent article with my recommendations for the best places to go in Asia in December. It’s got many more choices than the article above, with weather information for all of them. Closer to India, I think Sri Lanka is very nice in December, although it’s somewhat similar to India in many ways and you may want something more exotic. In that case I think Thailand and Malaysia are the best choices for family holidays.
Located on the north Pacific coast of Costa Rica, the 15-mile peninsula is home to lush jungles, postcard perfect beaches, and five-star hotels. It is decidedly remote (the nearest “town” is a 45 minute drive away) but sometimes, remoteness is exactly what a winter getaway calls for. Though Papagayo is the kind of place where you might be tempted to never leave the confines of your resort—there’s an Andaz, a Four Seasons, and a community of luxury villas to rent—it also caters to adventure lovers, with activities like ziplining, jetskiing, and four-wheeling through the jungle. Stick with later in the month to avoid any lingering rain (rainy season goes from May to early November.)
Thank you. If you want a sunny destination that is affordably reachable from Germany in November, the Canary Islands is the obvious choice. Tenerife is the largest and easiest to visit, and it’ll be warm enough to sunbathe and everything else in November if you stay in the area in the southwest of the island around Los Cristianos or Playa de las Americas. The “culture” around there will be a small mix of locals and a larger mix of people from northern Europe, so it’s interesting, although not as authentic as some prefer. Still, for great weather and great prices in November, it’s your best choice.
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.
As for alternatives, you might have a look at my recent article with my recommendations for the best places to go in Asia in December. It’s got many more choices than the article above, with weather information for all of them. Closer to India, I think Sri Lanka is very nice in December, although it’s somewhat similar to India in many ways and you may want something more exotic. In that case I think Thailand and Malaysia are the best choices for family holidays.
Located on the north Pacific coast of Costa Rica, the 15-mile peninsula is home to lush jungles, postcard perfect beaches, and five-star hotels. It is decidedly remote (the nearest “town” is a 45 minute drive away) but sometimes, remoteness is exactly what a winter getaway calls for. Though Papagayo is the kind of place where you might be tempted to never leave the confines of your resort—there’s an Andaz, a Four Seasons, and a community of luxury villas to rent—it also caters to adventure lovers, with activities like ziplining, jetskiing, and four-wheeling through the jungle. Stick with later in the month to avoid any lingering rain (rainy season goes from May to early November.)
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.
×