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.
Uruguay is an interesting place. It seems to be a less modern and less developed version of next-door Argentina. Buenos Aires is a larger and more interesting city than Montevideo. There is a town there called Colonia, which is worth a couple days if you like old and charming cities. But most people who go to Uruguay either go to one of the posh beach resort towns (mainly Punta del Este), or they go to the tourist cattle ranches, which are surprisingly popular. If you haven’t been to Argentina yet you might find that it has more and different options, such as the Mendoza wine region and the mountain resort town of Bariloche.
November is a pretty slow month all over the Caribbean. I just tried a few random dates in the middle of the month and I’m seeing all-inclusives starting at US$142 for two people including all taxes on Expedia.com. There are many more closer to US$200 per night, including many that get very good guest reviews. I stayed at Bahia Principe Luxury Ambar, which is an adults-only hotel within their huge complex there, and rooms are US$198 per night for two people, fully all-inclusive. So the resorts are showing some very good rates considering the quality you get there.
Actually, all of my best suggestions for those things are in the article above. One challenge you’ll have is that all popular tropical destinations have their peak weeks at the end of December because so many people in cold areas have that time off. So flights to Central or South America are going to be fairly expensive, although buying soon can help. For hiking and views I think Costa Rica could be a good choice, or Nicaragua. You could also go to Bariloche in Argentina, though it’s probably not worth going all that way unless you were also going to spend some time in Buenos Aires and such.
Most of the destinations below are in Latin America and Southeast Asia, so depending on where you are starting from it might be a rather long flight to get there. Many of us can take two weeks or even more around this time of year, but that fact means that all of these places do get crowded and raise hotel prices for the weeks around Christmas and New Year's. Speaking of that, we have a separate list of cheap and warm places to go over Christmas and New Year's, only listing beach areas around the world with affordable hotels during that period.
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.
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.
I haven’t heard much about Zika in quite some time, but I just checked the current CDC map and evidently it’s still out there. I also remember hearing that it’s really only pregnant or potentially pregnant women that are at much risk, so perhaps that is what you are implying with the kids in their 30s. I’m no expert on Zika and I’ve visited many places on the map in recent years without much worry.
The Canary Islands are always an option and the weather in November is pretty decent. I spent almost a month on Tenerife a couple years ago and I thought the nightlife was mostly pretty cheesy, although at least the drinks are cheap. I think in summer the nightlife there might be good, but in the other months I think it’s pretty quiet because it’s mostly older visitors from northern Europe.
As the year winds down the parties amp up, none more so than in Scotland’s capital, where Hogmanay celebrations see flaming torches, fireworks displays and night-long parties take over the usually quiet cobbled streets. Slightly more sedate, the Caribbean’s southernmost island Trinidad simmers with stirring Spanish-style musical performances as the locals usher in the start of the dry season.
Of course in November you can pretty much forget about Europe if you want warm weather and little chance of rain. Fortunately you can go almost anywhere in Latin America and through many parts of Southeast Asia on a cheap flight, and you'll be in the sun with shockingly low prices, easily making the flight duration and cost worthwhile. The best holiday destinations in November are found all over the world, which you'll see on the list below.
One thing about Cancun that is interesting. Cancun itself is essentially a very long beach sticking out into the Caribbean that is lined with high-rise hotels and time-share properties. Except for a busy area at the corner of that peninsula, most of the hotels are spread out quite a bit, so there aren’t many things that most guests can walk to. Many people love it and are happy to basically stay in their own hotel most of the time, and maybe take a taxi down to that busy corner area once in a while. Personally, I’m a much bigger fan of Playa del Carmen, which is a full-on tourist town about 50 miles south of Cancun. It’s got hundreds of small hotels, restaurants, bars, shops, and everything else a visitor wants. The beaches aren’t quite as nice, but I find the town to be very fun and vibrant. Also, up and down the coast from south of Playa del Carmen to north of Cancun there are large resorts that are far from each other and on huge properties. Many of them are all-inclusive, so that is another option.
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.
The food, including its famous ceviche dishes, is a particular highlight here, and the tourist district of Miraflores is packed with interesting and cheap restaurants. Basic and cheap hotels are in the same neighborhood, so it's a better alternative to the historic center of Lima for most people. By the way, the rainy season in Cusco starts in December, so the trails can sometimes be cut off, although many people go anyway.
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.