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14 days in Italy

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I am a 43 year old single male traveller, going to Italy from 8-21 July. Landing and departing Rome. On a tight budget and don't want to spend more that 100 euro max/night acc. I have an idea layed out for my trip.

Landing at Fiumicino midday on the 8th and take train to Pisa, then two days in Santa Margharita and then two days that I'm not sure what to do, then two days Venice, 3 days Florence and then to Rome until I depart the evening of 21 July. How does this sound?
I always suffer from jetlag (or perhaps just tired as I just cannot sleep on a plane). I prefer to sleep in as few as possible places as I feel I'm losing half a day everytime I need to relocate.

What should I do with the 2 uncertain days in my itinary?
How does my itinary look in general?
I would love to spend a little time in the very small villages, but will it be possible to get transport there?
Is it better to rent a car than to use the train?I do not want to drive into cities as I struggle to adapt to left hand driving. I see that a train pass is a good thing but if a understand correct you still need to pay extra for a reservation- is that correct.
Do I need a phrase book or do most Italians speak English (which is my 2nd language)

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