First as far as the short tours go, I've tried to stretch things by including holiday weekends such as Memorial Day/Labor Day or 4th of July. Christmas isn't ideal time in northern hemisphere, but I've either gone south (Florida, California, Texas) at times business is slower.

Now as far as longer tours go, I've probably been fortunate in choice of industry/company and luck but while working I've been able to get absences of 3mo, 12mo and 10mo in the past 15 years. Those were while working 23 years at the same company (no longer work there). There were a few things that helped me be able to get those absences:

1. I worked with my bosses and made sure it wasn't a surprise. I had very good relations with all my bosses and around evaluation time several years before I already planted the seed that I really wanted to get the next project or two done but then be able to take a break, refresh and jump into something new. About a year before I became more concrete with rough dates and times. In months leading up, I made sure I had groomed successors and otherwise everything was in place.

2. I worked at a large company, where occasional leaves of absence occur for legally protected reasons such as maternity or military service. Hence, there were policies and procedures in place and the organization knew how to deal with them. Extended travel is not the same legally protected leave, but with the right relationship with management I've been fortunate.

3. When not on bike tours, I worked very hard and was generally considered a top performer. I also kept up my skills and set aside some extra $$. That gave me the ability if necessary to use the extended bike trip as a transition to another company, but my current company also saw this and was willing to meet my life goals (discussed early as per #1 above) and hence they also saw benefits of putting me into "LOA status" and finding the next assignment on my return.

There was an element of luck involved here and I was fortunate to work in an area of software that has paid fine. I also made some choices in my personal life in living well below my means, saving and otherwise being willing to take a risk - to prioritize those extended tours as something worth working towards in life. For example, I've been car-free for 10 years, took in room-mates to help with the mortgage, bought a lot less house than I could afford, etc.

So the combined sequence for me has been to work four or five years, take an extended sabbatical and jump into a different role usually with the same company. At some point that luck might run out, but I've been fortunate so far.