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14 Nights in Italy

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Lovers of Italy
After traveling in France with wife, I will head off, unfortunately, solo for Italy. My plan is as follows: arrive Venice 30 Sept for 4 nights, depart via train for Spello 4 Oct, rent car and stay for 4 nights, depart via train for Rome 8 Oct, depart Rome for Boston via Madrid with overnight in Madrid. Sounds weird but I save on the free air miles 'taxes' by going that route vice direct to Boston even with the hotel thrown in. I have some doubts about whether I am trying to do too much, ie would it be better to spend more time in Venice, say 5 or 6 nights and go directly to Rome. On a previous trip, I was able to spend 4 quick days in Rome and fell in love with the place and want to do some 'slow travel' there. See the art, walk the city, sit in the piazzas and relax with a carafe of wine....every day! Actually, the same can be said about the entire 14 days. Opinions welcome. Lastly, I arrive in Madrid at 530pm and depart next day at 1230pm. Any ideas?
Thank you

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