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Italy 14 days Rome Siena Florence CT, help with itinerary

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Greetings, We have never visited Italy and do not want to be drained at the end of our vacation. Our questions is should we add a day to Rome (for 5.5 days) and take a day off of CT at the end?
Mon 9/9 arrive Rome and stay until Sat 9/14 or Sun 9/15
Sun 9/15 to Siena
Tu 9/17 to Florence (possibly renting a car to drive into the country for a day)
Fri 9/20 to CT
Sun 9/21 travel as late as possible to Milan just to sleep before an early morning flight home on Monday at 630am.
We were thinking if we left Rome on Sat 9/14, we would spend another day at CT.
We thank all for any help they can give us,
Kimberly

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