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Italy Itinerary- any changes you would make?

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I am going to Italy from March 21-April 5 with my boyfriend, sisters, and dad- none of us have ever been to Italy before. I would like to see as much as I can while still having a relaxing trip (last time we went to Europe we were constantly on the go- I barely remember any of it and I do NOT want that to happen this time).

This is the itinerary so far. I've never planned a trip before and I am very very lost with where to begin, what to include, etc. Some background on us: my sisters and my boyfriend will be happy with just about anything we do, My dad likes to see EVERYTHING but I'm sure he would enjoy a slower paced trip if we still see a lot of the main sites, we are all wine lovers.

I would like your opinion on if this is a realistic trip, which places in Tuscany to see/ do you agree with the places I've chosen? and what to see in Venice. I'm least excited about Venice so I have barely done any research.... that is why I left those days blank. My dad wants to see Venice in case you are wondering why we are going.

Day 1: Arrive in Rome at 7:05 am. Pantheon, Trevi Fountain, and Spanish Steps. Visit the Piazza Navona.
Day 2: Pompeii and possibly a stop in Naples
Day 3: Colosseum, Roman Forum and Palantine Hill
Day 4: Vatican City/St.Peter’s. Visit the nearby Castel Sant’Angelo and the Campo dei Fiori
Day 5: Siena (our home base for the nights in Tuscany). Explore Siena
Day 6: Day trip to Montepulciano and Pienza
Day 7: Day trip to San Gimigana and Volterra
Day 8: Chianti
Day 9: Florence: Piazza della Signoria and the Ponte Vecchio. Piazzale Michelangelo.
Day 10: Florence: Uffizi, Accademia, Bargello
Day 11: Then visit the Palazzo Vecchio, the Pitti Palace and the Boboli Gardens
Day 12: Duomo (plus the bell tower and the baptistery, & perhaps the Duomo Museum). Medici Chapels, Santa Croce, Santa Maria Novella, Orsanmichele.
Day 13: Venice
Day 14: Venice
Day 15: Head home

If this itinerary seem like a jumbled mess I apologize... I need some guidance.

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