When less busy and an extended weekend seems in order, I go to ctrip.com (note: I live in China, but I'm sure there are equivalents for flight/train details whe

When less busy and an extended weekend seems in order, I go to ctrip.com (note: I live in China, but I'm sure there are equivalents for flight/train details where you are) and see where on a mental list of places I like / I would like to go in China / East / Southeast Asia seem cheap, and if something seems really cheap, I get a Friday and/or Monday leave approved then book the flight. For what to do and places to stay I tend to go to the Reddit sub-page for the city/region and wing it from there. Reddit can have quite a bit of noise and group-think, which just takes getting used to, but the signal can be a true gold mine. I don't post unless I've got something really specific about a place that's not been asked before. And simply as a European in Asia for a long time, where other foreigners and internationally-minded locals tend to migrate here and there quite a lot, a network gets build over LinkedIn, WeChat, Facebook, etc, that there's invariably someone I've crossed paths with living where I want to do, so if I need a 'meat search engine' answer to a question I have it, or can suggest to hang out for those I know better. So, that may or may not be applicable to you, but that's how I plan, or really don't plan much at all. Do always have medical insurance when travelling. Check if your employer covers this. I've thankfully never needed to use it, but it gives a peace of mind for low probability high risk events.