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Backpacking Europe in the Winter

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Hi!

This message consists of:
My travel plans, questions on whether to by a Eurorail pass or flights, and questions on proper attire for winter in Europe

I am an American planning on traveling through all parts of Europe from December 26th to mid-February. I will start my journey in Lisbon with my girlfriend, and travel through Spain and France. Those are my initial plans, and I hope to do this within 2 weeks. After the two, I have no idea where I'm going or what I'll be doing.

I need help deciding whether to by a Eurorail pass or to plan to just by airplane tickets. If I were to do the latter, I am afraid of needing to pay check-in bag fees. This brings me to my next question: for a month and a half of traveling, what size backpack should I purchase? I was looking to by a 55 liter, but my friend will let me borrow his larger 85 liter. Should I borrow his backpack, or is it too big?

Finally, what shoes should I bring along? I was thinking water-proof hiking boots and a pair of sneakers. What are your thoughts?

Thanks!!

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