Everyone is different. There are those who plan every last detail of their upcoming trip, and there are those who prefer to simply 'wing it'. Where do we fall on the spectrum? Well, the answer isn't clear cut.
The amount of planning and research that I carry out prior to departure day is all part of the anticipation of the trip. This feeling of eagerness is a great aspect of the whole travelling experience; at the very least it is wicked mood booster! That being said however, the thrill of spontaneity is an experience we equally enjoy. Nothing feels more freeing than to just drop it all and live in the moment. Sounds cheezy? Very. But for the best possible outcomes, we find it's best to have a mix of both planning styles (or lack thereof).
For instance, Jonathan once skyped me while he was on his way back home from a business trip and we decided last minute we wanted to go camping that very night. From a skype call from Chicago's O'Hare to swinging by the airport at 9:00pm in Montreal and proceeding to drive an hour north (followed by a 45 minute hike with all our gear); it felt wonderful to bask in the moment. During the drive north, we saw multiple displays of fireworks as it was the eve of St-Jean in Quebec. At our campsite atop a mountain we were surrounded by dozens of fireflies. Aside from the near encounter with a black bear in the morning, it was an awesome yet short-lived experience.
As a general guideline, I like to leave the truly spontaneous getaways for the short but sweet trips; the few days or even hours at a time that you have available between work, family, and social life. That isn't to say there isn't any flexibility on longer travels; in fact, the other part of my reasoning behind somewhat thorough planning is that it eliminates the risk of confusion and maximizes the potential for having a great time. I'm not talking having every hour scheduled here.. far from it.
I've broken down how I plan/research for this kind of travel, and also explain the merits of this "system".
I prefer this method of planning as it doesn't tie you down to a specific schedule; you have the flexibility to be able to deal with weather conditions. "You do all this only so you can deal with the weather?" Nope! Jonathan and I are big proponents of efficiency and this planning 'system' allows you to not only save on the cost of gas, it reduces your carbon footprint.. good all around! It may seem like a long process but in reality it's just something I casually do for about half hour to an hour at a time while watching Youtube or Netflix.
Knowing your potential activity options for a given day doesn't necessarily mean you aren't 'living in the moment'. It puts your mind at ease and it serves as a base from which you can veer off of and do something spontaneous. In my opinion, it's the best of both worlds :)