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Italy in 11 days... Possible?

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DH and I are planning a trip to Italy in July. We will fly into Venice and out of Rome. I have family in Trieste and Rome so these stops are a must. DH is about to start med school so, with school loans, school, and 1 income this is it for many years! With that said we want to make the most of our time there. Below is our ideal itinerary. Is it too much in too little time? Or possible?

Day 1 arrive in Venice in morning site see, walk around
Day 2 Murano or just more site seeing in Venice
Day 3 Trieste to visit family
Day 4 Trieste, evening train Trieste to Florence
Day 5 half day trip to Chianti walk around Florence in evening
Day 6 half day trip to Pisa, night train Florence to Rome
Day 7 Rome
Day 8 Rome
Day 9 day trip to Pompeii
Day 10 flight back to states

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