The length of your trip should be based on the season you go in. Or vice versa. What is your intention for this trip? To see stuff or to go on vacation? If it's to see stuff, you probably want to go in spring. The weather is perfect for spending all day outside. You wont boil or freeze.
If you're planning to do more of a vacation and hit beaches, obviously you want to go in summer. Just keep in mind that the good beach countries like Spain, Portugal, Italy and Greece are ridiculously hot during summer.
I'm not a planner, so I'd just buy a ticket to the cheapest city to fly in to (probably London) and then start talking to my fellow hostelites. Go smoke a doob in Amsterdam, then catch a train to Paris. Maybe a Ryanair or Easyjet flight to Rome, take a train to Amalfi, take another train to Brindisi and then a boat to Greece. Then just take trains up through Eastern Europe and check out the smoking hot chicks in Croatia. Train to Prague, flight to Munich, fly home from there.
Take it as it comes. I was a master at making people stay at my hostel in Rome. So many people arrived thinking they would do Rome in two or three days and then they'd end up staying a week and cutting out a couple other cities. The people who planned their trip down to the day were stressed. The people who were just going with the flow (always the Aussies and Irish) were having the best times.
Another thing to keep in mind is where you're going to stay. If you go in high season, you probably have to book your hostel well in advance. This reduces your ability to just go when and where you want. If you go in spring, you can usually just book your hostel online the night before you head to the next town.
If you arrive in a town without having made sleeping arrangements, there are usually guys at the train station selling beds at hostels. Only pay for one night and then go assess the town to see if you're in a good location. Chat with other backpackers to see where they're staying and how much they're paying.
There is a cool comraderie that develops between backpackers the minute they land in Europe. Everyone is approachable. Just chat someone up and they'll know something you don't know and vice versa.
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