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Questions about traveling by train and foot in Spain, Italy, Germany

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Hello,

I will arrive in Madrid Spain on May 1st. I have bought my plan ticket and am currently looking into train tickets/reservations. I have a very tight budget. I plan to be doing more "couchsurfing" than hostel hopping. (This is my first time backpacking/traveling Europe)

Here is my itinerary;
May (Spain)
1 - Madrid (Arrival into Europe)
till
7 - Madrid (train to Valencia) book w/ http://petrabax.com/renfe/ flexi pass about $90
8 - Valencia
till
13 - Valencia (walk to Vinaroz) 144 km = 30 hours
20 - Vinaroz (train to Barcelona) book w/ http://petrabax.com/renfe/ flexi about $50
21 - Barcelona
till
31 - Barcelona (departure from Spain to Venice) book w/ kayak - Veuling (***TO VENICE*****) about $150 for flight, baggage, and additional fees...

June (Italy)
1 - Venice (Arrival into Italy)
till
8 - Venice (train to La Spezia) book w/http://www.trenitalia.com/trenitalia.html about $50
9 - La Spezia
till
14 - La Spezia (walk to Florence) 185km = 38 hours
22 - Florence (train to Rome) book w/http://www.trenitalia.com/trenitalia.html about $50
23 - Rome
till
30 - Rome

July ( Italy/Germany)
1 - Rome
till
2 - Rome (flight to Munich) search w/ Kayak - book w/ (Air Berlin $150...ect) or (Veuling $180)
3 - Munich (Arrival into Germany)
till
9 - Munich (train to Dresden) book w/ DB BAHN about $100
10 - Dresden
11 - Dresden (walk to Berlin) 180km = 40 hours
till (walk)
19 - Berlin
till
27 - Berlin (Departure to America)


My questions are:

1. I want my trip to be spontaneous; I don't want to have to leave one place just to catch a train. I want to follow my itinerary but also have room to change it. From what I gather a Flexi Pass option train reservation gives you the option to change the dates, but certain fees might be added to change the fare. SO, Would it benefit me to buy the tickets on the date of departure at the stations, keeping in mind (according to my plans) I only need to travel by train twice in each country. Will making the reservation a month or two in advance save me money, along with a Flexi Pass option ticket, benefit me more?

2. I don't want to just spend time in the cities...i don't think i will have enough money to take buses out of city and then back again. So in order to see the country I was planning on walking through some towns. Once in Valencia, my plan was to walk for several days, sleeping at night where ever I can find a place that is secluded, stopping in towns along the way for supplies, food etc. then take a train to Barcelona in order to arrive before the 24th. In each country I set aside about a week or so to walk to a destination of departure to a city. I have no clue what sort of terrain I will encounter and if it is even legal just to find a tree somewhere outside of a town and sleep till morning.

Any and all info that you can give me would be great. I have never traveled before in Europe; I have been researching site after site trying to piece together my own trip, my equipment, lodging, as well as my activities in each place. Please give me your input. I appreciate it. Thanks!

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