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backpacking through Italy

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I am putting together a 20-day itinerary for a backpacking tour of Italy at the end of May 2014.

I've researched a little bit about the different places that I would like to see on my trip. Being that this is the first time I am traveling to Italy, I don't know how feasible it is to do all the things I would like to do in the time frame that I have. Any advice, recommendations, or tips on accomodations, train passes and routes, sight seeing spots, diners, shopping, etc.

Here is my itinerary for 20-day itinerary-well, 18 days two days must be allotted for the travel to Italy and back home.

Fly into the Fiumino Airport

3 days in Rome: will be doing all the regular tourist attractions and some exploration of the city.
then train to
3 days at the Amalfi Coast: day trip to Positano and if all possible, go to Capri for a day.

then train to
4 days in Siena, Tuscany, and Florence
then train to
5 days in Cinque Terre -would it be possible to take the train into Switzerland to Chamonix and see Mount Blanc as day trip?

then train to
3 days in Venice

And fly out of Venice airport to come back home.

Looking forward to hearing from everyone. Thanks in advance for your suggestions and comments.


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