One of my favorite trips involved planning as far as a train trip and booking a hostel. But beyond that my group basically blew off every plan we had and hung around the hostel because they had a really nice free pool table and really good cheap food and booze.
That is probably one of my top three trips of my life. I find my memories compressed because it was basically 5 days of Groundhog Day but it was a great time.
Making a daily log sounds miserable to me but then again I strongly dislike journaling.
Then again the phenomenon you bring up might contribute to what people love about Disney World so much. You have to do a lot of planning to get a lot out of it, and therefore you remember everything you did clearly because so much time was spent planning. I think I could tell you every restaurant I went to on my last trip since I had to fight for reservations and I was setting each day’s plan months ahead of time.