Is this thread just about holidays, ie no one wants to know about my current fascinating project management concerns?
Assuming so, I’m a fairly solid planner for holidays - flights/apartment (switched to apartments since taking the kids with us - having kids with you increases your planning requirements comfortably two-fold I would say) booked at least a term in advance, airport parking and transfers where necessary booked shortly after, some form of guidebook purchased a month or so in advance and digested (plus some Duolingo done if I have the time). Have a rough plan of what we want to do while there, but play this a little by ear when on the ground. As mentioned above, pre-planning allows you time to go with the flow once you arrive.
The TV on the contrary plans approximately nothing. We went up to Scotland to visit her family and spend a couple of days at The Fringe and she said she was going to sort it all. To zero surprise, she basically left it until a couple of days beforehand to do anything. This resulted in us staying in an expensive hell hole in Edinburgh - so bad that we complained to Booking.com and got half the cost back. When we flew to Croatia the other week, I went to the airport straight from work and she drove from home. She left 90 minutes later than planned and had the incoming flight been on time we would have missed it completely. As it was we had to sprint through the airport with two small children in tow to make it by the skin of our teeth. That was a fairly stressful experience 


Incidentally, anyone planning for May 2019 half term then Easyjet flights go on sale on September 20th 