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23 days in Italy - itenerary HELP

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Hi All!
My hubby and I are planning our first trip to Italy for Spring 2015. We have 23 days but are having a really hard time figuring out where to go. We know we want to spend the first few days in Lake Como just to relax. We also definetly want to go to the Dolomites and do some hiking. And at the end of our trip we want to do Rome and the Amlafi Coast area (pompeii and what not). We originally planned to change hotels every 1-2 days and we decided we would rather stay put and take day trips from a central location. We are most interested in outdoors and history. We are NOT interested in nightlife or fine dining. I welcome all of your advice and suggestions. Itinerary and a list of my key questions follow.
1. We have 5 days planned for Florence - what day trips are reasonable from this location
2. Is Assisi worth one night? - If not please make a suggestion
3. Suggestions for a nice/romantic place to stay in Lake Como
4. For hiking the Dolomites is Bolzano or Castelrotta the better choice for sleeping or do you have a better suggestion?

Itinerary
Day 1 - Arrive in Milan - transfer to Lake Como
Day 2 - Lake Como, sleep in Varenna (?)
Day 3- Lake Como, sleep in Varenna (?)
Day 4 - To Dolomites via Verona, sleep in Bolzano or Castelrotto (?)
Day 5- Dolomites, sleep in Bolzano or Castelrotto (?)
Day 6- To Venice
Day 7 - Venice
Day 8- To Cinque Terre
Day 9- Cinque Terre
Day 10- April 17: Pisa, then to Florence
Day 11- April 18: Florence, sleep Florence
Day 12 - April 19: Florence
Day 13- April 20: Florence - day trip to Siena
Day 14- April 21: Florence (?)
Day 15- April 22: To Assisi (by bus)
Day 16- April 23: To Sorrento
Day 17- April 24: Sorrento, Naples
Day 18- April 25: Sorrento, Pompeii
Day 19 - April 26: Sorrento, Capri
Day 20- April 27: Morning to Rome, sleep in Rome
Day 21 - April 28: Rome, sleep in Rome
Day 22 - April 29: Rome, sleep in Rome
Day 23- April 30: Fly home

Thanks for your help and suggestions!

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