As far as trip-planning in general, I’m no expert, but I’ll pass on my own technique which has worked well at least for me.

0. If you don’t have the passport yet, apply for it right away. It lasts 10 years, so don’t risk waiting too long and not being able to start a trip as planned because it hasn’t come yet.

1. Decide in advance what kind of things you want to see or do: art? historical places? cities, villages, or countriside? Then throughout the years, write down places and what is interesting about it in a computer file as you discover them through ordinary reading of your books, magazines, and internet surfing. If you are going to want to go to concerts, opera, or theatre, start surfing to some of the web pages and study the schedule of upcoming productions.

2. If your list is going to include a big city, then buy one of the tour guides for that city at Barnes and Noble, and start perusing it for additional ideas of interest.

3. As the time approaches to buy airline tickets, print out a google-map spanning the places you have selected, and start to work out the path to follow to get as much as possible as efficiently as possible.

4. Reserve accomodations for the first and last night in advance. Additional reservations may be done, especially if you are worried about availability due to time or place. However, allow at least a few nights here and there to not be reserved so you can adjust your itinary on the fly.

5. Renting a car opens up lots of possibilities, especially for visiting the hinterlands. If you are going to spend all the time in just a few cities, then the railroad might be a better choice.