This is one of those things I know in the end as much as I am scared beyond my wits I just have to do it. This is usually what happens when I think about trips: I question what I should do and start researching it. I immediately shut the browser remembering that a planned trip is not a trip at all. In the end I never plan anything and ultimately don't end up going. What I figured I'd do is plan minor things like hotel and transportation then leave the rest to the wind. Some healthy balance between my need to be in control and need to experience life.
The problem with that is that you miss out on cool places and sights to visit. I grind through travel sites and try to find blogs written by locals to build a list of things to do. For example, I did a stopover for a few days in New York on my way from the Netherlands to Canada. I would've never found great views of the city, ultra-hip places, the best pizza or the architectural gems if I didn't do some research beforehand. But I had no plan on what to do when. For me travel is about being flexible and just having an awesome day. It's a balance that works for me. I immediately shut the browser remembering that a planned trip is not a trip at all.