I’m at 17 years. I’ve traveled to fulfill obligations since, but the last time I planned PTO to go somewhere and relax with no set agenda was 2006.
You’ve got me beat. I’m sorry.
Mine was in 2013. If someone had told me that “being your own boss” meant this, I think I would’ve hesitated.
I guess I’m very different. I went on a trip for a week in May, and have 4 more planned into next year, though I intend to “WFH” during some of them. I don’t want to burn all my vacation time. I’ve worked out a way to force myself to go on more trips for fun and my hobbies.
That said, a trip like this still tends to have some things planned, because you need to buy tickets or whatever in advance a little bit. I am lucky in that I can do this.
Last year I’ve spent a week in an hospital… nah, scratch that, it was unplanned and had my work phone with me.
“Planned, just to relax, no set agenda”, that must’ve been sometime in the 1990s, so at least 25 years.
We all had Penn & Teller tickets (totally worth $100 a pop in '06), but the rest of the long weekend was “fuck around in Vegas with our mid-20s livers and cheap hotel rooms we only want to sleep in.” My college roommate won his and his fiancee’s entire trip costs with five minutes to spare before the airport pickup.
2016 for a week in Corfu on my honeymoon.
Unless you’re counting a week off here and there to just chill at home, in which case, April.
