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Planning a month in Italy - could really use some help!

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Hello all, I have begun the tedious task of planning an extended vacation in Italy for my Grandpa and I. His parents immigrated from Italy in the 20's and so we are going to visit their birth places. This trip obviously means a lot to us and it would be great to receive tips from experienced Italy enthusiasts!

To begin with, we are looking to save as much money as possible, considering the length of the trip, so I've pretty much ruled out the summer months. I was considering some time between Feb-April. We will rent a car.

He would like to have a 'base' somewhere near Rome, and we will definitely be visiting Ortona, which I understand is within driving distance. He may want to visit parts of Foggia too, but we covered that one pretty good last time so I'm not too sure. He would like to spend about two weeks in this area, then start moving north. I believe Florence and Pisa will be necessary stops, and Venice will probably be as far as we end up.

Can anyone provide tips as to where to stay for extended periods right outside of Rome (or in Rome if the price is right)? We may need a couple of bedrooms if his brother decides to go. Any tips on restaurants and markets is appreciated. If you have any stops along the way to Venice that you particularly enjoy I would love to hear about it, as we may add it to our itinerary.

The good thing is, my Grandpa is very relaxed and flexible, which makes travel with him a breeze, but it also makes things difficult to plan since he is not terribly specific about anything. He doesn't know how to use a computer so I'm gathering as much info as possible to show him. Admittedly this is a bit overwhelming, especially since he is very spontaneous and decided last night that we need to go asap. :)

Thank you for any help you can provide.

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