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My (Almost) Final Itinerary - Italy 17 days

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OK...Here I go. I have posted several threads and have read numerous suggestions. Here is what I came up with. While reading this, please keep in mind I don't have any hotels booked yet, so edits are welcome. I am looking for suggestions based on the Musts(and wants) I list below.
With arriving in Rome and departing from Rome, I NEED Rome to be my last destination.
We arrive in Rome at 8am on June 9th and Depart Rome on June 25th at 1pm Days: 17 including arrival and departure. Given that I will be in Florence by 1pm, please suggest what I can do on our first day since we will have many hours.

Here is what I am looking to do:
I want to limit myself to 3 or 4 hotels, but I PREFER 3.
I prefer NOT to stay in Venice.
I can stay in Siena or another hill top area with nearby restaurants and wineries.

My MUSTS:
Major sights in Florence and time for just roaming the streets
Pisa.
Emilia Bologna Region - Please include restaurant recommendations and must see sights/walks/drives
Venice
Siena/Greve and other tuscan towns within reasonable distance of Siena and Greve. I would like to drive(Car) in Tuscany visiting Siena, Greve, San Gimignano.
Capri
Pompeii
Hike Amalfi Coast(PLEASE recommend a good hike trail)
Amalfi Coast drive and leisurely day
Positano
Amalfi
Ravello
Minimum, 3 full days in Roam

Things/places I would like to do/visit

Visit Orvieto. I think it's best by train from Rome, so please keep that in mind.
Visit Cortona
Visit Verona
I would to visit the Cinque Terre.

Here is what I was thinking:

Itinerary Option 1:

Day 1: Arrive in Rome 8am and head to Florence by train
Day 2: Explore Florence
Day 3: Venice
Day 4: Pisa
Day 5: Emilia-Bologna Region(Visit Bologna, Modena and Parma) -
When in this area, I would like to visit the Savigno to dine at Amerigo dal 1934
***Should we take car or train
Day 6: Visit Siena/Greve/San Gimignano (CAR). Thinking of leaving car in Siena and depart back to Florence by train.
Day 7: Depart Florence for Sorrento - What is the best way to get here?
Day 8: Capri
Day 9: Pompeii
Day 10: Amalfi Coast
Day 11: Hike - Please recommend some hiking trails
Day 12: Depart Sorrento for Rome
Day 13: Rome Sights
Day 14: Rome Sights
Day 15: Rome Sights - Trip to Orvieto
Day 16: Rome Sights
Day 17: Depart for home

Itinerary Option 2:

Day 1: Arrive in Rome and head Sorrento. What is the best way to get here?
Day 2: Capri
Day 3: Pompeii
Day 4: Amalfi Coast drive/tour
Day 5: Hike (Recommendations on which hikes PLEASE)
Day 6: Depart Sorrento for Siena. What is the best way to get here? (Car or Train) If by car, what is 1 good stop in between worth while seeing? Please keep in mind I would like a car here.
Day 7: Explore Siena
Day 8: Depart Siena for Florence (car)
Day 9: Explore Florence
Day 10: Venice (Train)
Day 11: Pisa trip (Train)
Day 12: Emilia-Bologna Region(Visit Bologna, Modena and Parma) -
When in this area, I would like to visit the Savigno to dine at Amerigo dal 1934
***Should we take car or train
Day 13: Depart Florence Rome (Train)
Day 14: Rome sights
Day 15: Rome Sights
Day 16: Rome Sights
Day 17: Depart for home

Itinerary Option 3

Day 1: Arrive in Rome 8am. Train to Florence Hotel.
Day 2: Explore Florence
Day 3: Venice (Train)
Day 4: Pisa trip (Train)
Day 5: Emilia-Bologna Region(Visit Bologna, Modena and Parma) -
When in this area, I would like to visit the Savigno to dine at Amerigo dal 1934
***Should we take car or train
Day 6: Depart Florence for Siena (Car)
Day 7: Explore Siena
Day 8: Depart Siena for Sorrento (Train or Car...please suggest transportation)
***If we drive, what is 1 good stop on the way to Naples then to Sorrento?
***If take the train, which should I take? After arriving in Naples, how do I get to Sorrento?
Day 9: Capri
Day 10: Pompeii
Day 11: Amalfi Coast drive/tour
Day 12: Hike (Recommendations on which hikes PLEASE)
Day 13: Depart Sorrento for Rome
Day 14: Rome Sights
Day 15: Rome Sights
Day 16: Rome Sights
Day 17: Depart for Home.

Should I book trains prior to arriving in Rome after finalizing my itinerary? I will have a RailPass with 8, 9 or 10 train rides. With this pass, even if I book seats now, I will be able to cancel my seats(I think).

Thanks in advance for everyones feedback. Just like I tend to overpack for all my vacations, I seem to be overpacking this trip with activities. I want to make my time as much stress free as possible, but see as much as possible.

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