I've been referring to Rick Steves' Europe Through the Back Door for information on itinerary skills.My notes taken from this book can be found in my Research wiki.
According to RS' Itinerary Planning, here's how I put together my trip.
1) Research and decide on the places you want to see. Make a list and circle the destinations on a map.
France - Alps - Italy - Cinque Terre - Greece - Germany - Romantic Road - Rhine - Netherlands
2) Establish a route and timeline. Figure out a logical geographical order and length for your trip.
I realized that Greece is too far out of the way for this trip.
Paris - Rome - Florence - Venice - Germany - Amsterdam
3) Determine the mode of transportation.
My trip is linear and consists of cities that are all on the train line. After researching the locations and timeline, a 15 day pass is the best option for both budget and convenience.
4) Make a rough itinerary.
I worked out a geographically logical plan that fit into a 22 day venture. (I took a lot of guidance from a sample trip I found in this book - it pointed out some great places to stay overnight in that were off the beaten path).
Paris (3)
Gimmelwald (3)
Cinque Terre (2)
Rome (3)
Florence (1)
Venice (1)
Munich (1)
Rothenburg (1)
Bacharach (2)
Haarlem (2)