I did my first workation with my wife just over a year ago. We would have loved to stay longer, but in the end we were only able to stay for a month due to our circumstances. So it was perhaps a bit of a dip in the deep end as far as workations are concerned, but it was definitely a great experience that we can fully recommend. However, we found the planning challenging to say the least, so here is a short list of what you need to look out for first and foremost.