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How much flexibility to railpasses allow?

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In middle of january me and a3 friends (we we will all be 19yo students) are hoping to go backpacking in europe.

When my dad did this as a youngster, he got a railpass and completely winged it. However, this was before compulsory reservations were brought in.

Is it possible to still wing it? Can reservations be made a couple of days in advance, or do they have to be weeks in advance?

price isnt a big issue as i think ive accurately come up with a cost including all reservations, i just want to know if winging it is realistic.

We hope to travel
Paris -> Brussels -> Amsterdam -> Hamburg -> Berlin -> Contiki tour to Hungary -> Lichtenstein -> Venice -> Rome -> Pisa -> nice -> paris.

but we want maximum flexibility from hungary onwards, are we being realistic?

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