My "pin in the map" story was back in my university days in the eighties. I was backpacking Europe with a Eurail pass. I was halfway in my trip and had just taken an overnight train to Brindisi. I was burned out. While waiting to embark on the ferry to Greece, I saw a bunch of students get off the boat. One of them had the deepest of tans. I asked him where he got his tan. He said "Man, you have to go to Skyros, nothing there but goat farmers." After a couple of nights in ugly (to me) Athens, I hopped on a bus to Kimi and took a ferry to Skyros. Only two others disembarked and we were the only 3 tourists on the whole island. I ended up sharing a room with a guy from the UK and stayed a week to completely decompress living on calamari and tomato and olive salads. Left Greece with a really dark tan.
I have very fond memories of that first trip in Europe. I had a general idea of what I wanted to see, and armed with the latest volume of "Let's Go Europe", I would just hop on and off trains, go to the local tourist office to find a hotel. When all the cheap hotels in Venice were booked up, I just hopped back on the train and backtracked to Padua to find a place to sleep.
Nowadays, I am on tripadvisor and this forum, planning months in advance. All hotels and trains are pre-booked and usually all tix for attractions are bought online ahead of time. The only spontaneous thing we did in our November Spain trip was to make a last minute day trip to Toledo on our last day. Even then, I was a bit nervous because we still had to get back to the Madrid hotel to pack and check out later that night at 3am to catch a flight home.