An 800 mile road trip with my inlaws sitting in the backseat of my car. Worst weeks vacation of my life.
1988- I finally got leave after four months of deployment in Honduras, intent to come home to propose to my fiancée (my wife of 28 years), but her brother was killed AND my 97-yr-old great-grandfather died of heart failure within the first week. I almost wished I had never left the jungle.
A cross country trip, in the backseat of a small car, with my screaming two year old. Oy vey....I'm still cringing.
As a kid, going to Disneyland in California.
All the good rides were closed for repairs / maintenance.