The Maldives is amazing for relaxing beach holidays and it’s within your range. The tricky thing for most people is that it’s quite expensive for a shorter trip. Of course the Maldives is famous for its water villa resorts, and those water villas start at around US$350 per night. Nearly all of those resorts also have island villas and rooms and those can start at as low as US$100 per night, but you also have to pay for a speedboat or sea-plane transfer from Male Airport to your resort. That can be as low as US$100 per adult for the closer speedboat islands, and up to US$600 per adult for the more remote sea-plane islands. On a shorter stay, that obviously adds to the price. Speaking of that, I run another site all about overwater bungalows and I have links from an article on this site about the cheapest overwater villas in the world. Have a look at that list as it will show you the more affordable options in the Maldives, as well as even cheaper options in Malaysia and elsewhere.


In India I’ve always had good luck with the trains by booking at least a couple days in advance, and also being flexible and only going when an AC3 ticket is available. As you know, the actual train stations are nightmares. But every hotel has a person who can fetch a ticket for you by going through the back door and bribing someone at the train office. Like a AC3 ticket might cost US$20, and for an extra US$4, your hotel will go buy it for you and it’ll be waiting at the front desk later that day. It’s a pretty sweet system.
In India I’ve always had good luck with the trains by booking at least a couple days in advance, and also being flexible and only going when an AC3 ticket is available. As you know, the actual train stations are nightmares. But every hotel has a person who can fetch a ticket for you by going through the back door and bribing someone at the train office. Like a AC3 ticket might cost US$20, and for an extra US$4, your hotel will go buy it for you and it’ll be waiting at the front desk later that day. It’s a pretty sweet system.
I too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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