If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.
Hotel prices definitely go up in around Christmas so it's best to come early in the month if that's possible, but it's still a pretty good bargain even during the peak weeks. Book early if you can because the better and cheaper hotels will fill up first, of course. Also consider a side trip to the Mendoza wine region, Patagonia, or the amazing water falls of Iguazu.
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.
People don’t think of Moscow for winter, but it’s such a wonderful time to be there. The weather is no worse than what you’d find in New York City, and the huge advantage is the people—or, really, the lack of people! No masses of tourist buses descending on the Kremlin, no huge lines for museums (of course, we ensure our travelers skip all museum lines anyway), and no crazy crowds in Red Square. Something magical happens in Moscow in the off-season: It actually becomes more approachable and less intimidating. (Plus, December falls in the heart of the theater season, so for culture vultures this is the best time to visit.)
The largest national park south of Alaska, Death Valley is located 295 miles northeast of Los Angeles and 120 miles northwest of Las Vegas. Much of the park is below sea level, and it is surrounded by mountain peaks, often covered in snow. December’s temperatures are moderate, generally in the mid-60s during the day and 40s at night. Daily guided walks and naturalist talks are presented by the National Park Service, acquainting visitors with the natural beauty, history, geology, and wildlife of the area. Stargazers will be in awe of the Milky Way and starry nighttime skies of this “Gold Tier” Dark Sky Park, a designation by the International Dark Sky Association. The newly renovated Oasis at Death Valley (formerly Furnace Creek), hosts the elegant 4-diamond Inn at Death Valley and the family-oriented Ranch at Death Valley, offering visitors a range of lodging options and activities. At Furnace Creek Stables, guests can explore the valley floor or foothills of the Funeral Mountains on guided horseback rides. The Stables also offer carriage and hay wagon rides. Jeep rentals, tours, and a variety of hiking and walking paths provide many ways to experience Death Valley. Play golf at the world’s lowest elevation golf course or enjoy a rejuvenating spa treatment at The Inn.
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.
Escape the cold weather to sunbathe on the beaches in Rio de Janeiro and ring in the New Year with a fun celebration on Copacabana Beach. And while you're near Copa, visit the neighborhood and beach that inspired the song, “The Girl from Ipanema.” Don’t overlook the other beaches, including Baixo Baby for families, Praia do Arpoador for surfers and Sao Conrado Beach if you want to leap from nearby peaks and go hang gliding.
From November through February there are literally no European cities that could qualify as having “great weather.” We list Tenerife below because it's technically in Europe, although not really much of a cultural destination. Antalya, Turkey (which technically isn't even in Europe), has the closest thing to a sunny climate with acceptable temperatures. 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.
Bali is wonderful, or at least parts of it are, but they now have a volcano issue and those flights are very long and never cheap. Machu Picchu is incredible, but it’s a place you visit for half a day or so, and they actually have their rainy season at the end of the year, so it’s actually not one of the better times to go. Actually, you might consider a trip to Argentina, which is warm that time of year, though rarely scorching. Buenos Aires is a wonderful city that is pretty good value now, and you can also visit the Mendoza wine region and Iguazu Falls and Bariloche, which are all even a bit cheaper than Buenos Aires.
The hotel rates all over Goa are highest in December and January, but in Anjuna or Vagator they still start at around £10 per night for a private room with ensuite. The cheap places are quite shabby, so it might be worth spending more. Vagator has an amazing beach, but it’s often filled with Russians these days. Anjuna is famous for its beach raves and music scene, but I’ve honestly heard nice things about many other beach areas in Goa.
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