I am not a planner.
Sometimes a friend will suggest we do something together and if it's further out than the weekend my usual response is: "I don't know, that's too far out to plan!"
The only time I deviate from being a planner is for big important events. Especially when I have to buy an airline ticket.
I blogged before about some trips I've gone on where I have had no itinerary. I love those type of trips. They left me free to roam around on my own and to find my own adventures. But I can see why people make plans to see certain things in a new city they visit. Don't most places have a "must see" thing that one should visit while in the city or area? I sometimes had a vague feeling while wandering around in my travels that maybe I was missing out on something. But that feeling soon left as I found something to do.
I know a lot of people that are planners. I've even seen friends make plans months in advance with spreadsheets and all; planning out the trip to the minute. At best I think about packing things a day or two before my trip. I may grab a guide book if I'm going to a new city to see it it mentions good things to see. But I don't trust guide books all the time. My last trip to Key West the guide book said that an area on the pier was fun and a little more adult in the entertainment and it promised a great view of the sunset. When we got there it was very crowded and families with little children were everywhere. EW! We ventured out on our own and had a better time doing our own thing.
One of my favorite things to do is check the brochure rack at a hotel. They usually will let me know what is happening in the area and I'll go from there.
If you're a planner let me know what drives you. If you're like me and love to be spontaneous share a story or two, if you'd like.