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NEED ADVICE: 2 Months in Italy, 1 Month through Spain, Greece, and France

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I will be staying in Rome for 2 months with a host family (Geovisions - teach English program) and backpacking across Spain, Greece, and France for the last month, although, I haven't fully finished my itinerary on that yet. I was hoping to receive advice on which type of luggage I should bring and the type of travel.

Option 1:
Rolling suitcase + carry-on bag to hold my DSLR + lens + daily items.
Carry-on bag: http://www.langly.co/products/alpha-pro

Option 2:
Traveling backpack + messenger bag style camera bag for DSLR + lens
Backpack options: http://www.tombihn.com/PROD/TB0906.html
Messenger bag: http://www.onabags.com/store/messenger-bags.html

These options aren't 100%, just a few that I came up with. What are your thoughts on what I should do?

As I'll be spending 2 months living in Italy, I am planning to explore every city (Milan, Florence, Naples, Bologna, Venice, Le Marche, etc) and would like to know the cheapest option for getting around (besides walking). To get from Italy to Spain/Greece/France, I was looking at taking the EUrail. Would you suggest I get a "Select Pass" or buying the passes, "Point to Point"? Unless it's preferred to take Ryan Air.

I have less than 3 months to complete this plan and appreciate all your help.

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