Lovers of historic architecture should consider tiny Malta in November, which still basks in glorious warm weather as much of Europe starts to shiver. The baroque palaces, churches and fortifications of its harbour-hugging capital Valletta look much the same as they did 400 years ago, and are extra lovely when observed from a traditional dghajsa (open boat) water taxi. If a life on the high seas has always appealed, then charter a course for the Cayman Islands come November, when the serene Caribbean isle hosts Pirate Week, a fun-filled festival that includes costume contests, street dancing and a horde of swashbucklers ‘invading’ the island and capturing the governor.
It’s unfortunate and heartbreaking how many times I have recommended San Juan, Puerto Rico in the last few years. Once they get the power back on I’m sure it’ll be back to normal fairly soon after that, but I’m guessing probably March or later. And fortunately, Nate missed the Cancun area for the most part. Have you considered somewhere in the Cancun/Playa del Carmen/Cozumel area? I’m particularly fond of Playa del Carmen, and that flight to Cancun should be pretty reasonable for you.

Sri Lanka doesn’t really have a good infrastructure for budget travelers at this point. There are loads of nice hotels if you are willing to pay US$40 or more per night, but almost nothing below that except for a few hostels. I haven’t been to Palawan but I have been to Boracay and Palawan can’t be too much cheaper. Boracay doesn’t have many budget options either, so my guess is that Thailand or Cambodia is your best bet.
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!
If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger
If you are looking for first-rate destinations that are among the cheaper European cities, I’ll suggest Prague, Budapest, Krakow, and Berlin. You could visit all four of them by taking trains, or choose any one, two, or three. In December you can get quite a nice room in any of those cities, with Berlin being the most expensive by a bit. Food and attractions are also quite affordable in those cities.
If you are looking for a cheap, beautiful, and relaxing beach destination during December then Goa is ideal. This has become hugely popular with package tourists from Europe and Israel (and more recently Russia), and the facts that pretty much everyone speaks English and there aren't many cultural opportunities means that it's a perfect place to just vegetate in a beach chair for a week or two.
Venice can get pretty cold and they also have those famous Acqua Alta floods in winter, so read up on that before you go. But Rome and Munich should be easy to visit in December. One suggestion I will make is to consider visiting Rome for 3 or 4 nights and then base yourself down on Sorrento for the remaining 2 or 3 nights. Rome is one of those cities that is crowded and chaotic even in winter, to the point that just crossing the street can be frustrating, so many people get tired of that after they’ve seen the main sights. And Sorrento, on the other hand, is a lovely small city that is close to Amalfi, Pompeii, Naples, and the Isle of Capri, so it’s an ideal base to visit all of those. Sorrento is also cheaper than Rome, and a surprising number of locals speak English there, so it’s easy and pleasant. That time of year I’m not even sure if the tourist buses are running to Amalfi, although the local ones will be.
The last one is a 10 day trip for spring break 2018 most likely to be from March 9th to March 18. I’m thinking Europe but I don’t want to stay only in one country. I have so many options that I need someone to shorten the list in a way that it will work out. I want to go to Amsterdam, Rome,Venice,London,Barcelona,Zurich,Madeira,Dublin, and Madrid. (Amsterdam & Barcelona are a must).
As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.
I’ve spent a few weeks on Boracay, but not in early November. From what I’ve read, the monsoons there are usually not too bad, and it’s mainly a matter of a couple of hours rain in the afternoon on the bad days. Throughout the Tropics it’s very rare to get rain all day on any given day, and I’ve spent many months in those areas during rainy seasons. So early November isn’t ideal, but if it’s the only time you can go I still think you’ll enjoy it. One nice thing about Boracay is that the hotels are all basically on the beach or right off the beach, so even if it does start raining you can be back in your room in like 2 or 3 minutes. Best of luck with this. -Roger
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
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