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Italy and Greece in 14 days

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Hello guys, this is my first post and would love to get some help on my trip planning to Italy and Greece in Sept this year!! I only got 2 weeks because of work :( and here's what i came up so far:

Day 0 - departing canada
Day 1 - arriving Rome around noon and check in hotel etc, asuming most day is pretty much gone, dinner and rest up for the vacation
Day 2 - Rome city
Day 3 - Vatican city
Day 4 - Pompeii (1 or 2 days??)
Day 5 - if 1 day in Pompeii, then fly from Rome to Santorini today
Day 6,7&8 - Santorini
Day 9&10 - another Greek island or Athens?
Day 11 - fly to Florence
Day 12 - Florence
Day 13 - Florence, and come back to Rome in the afternoon
Day 14 - Rome
Day 15 - coming back to Canada

Feel free to criticise and yell "impossible" or "wasting time" at me. Thanks a lot!!!

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