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Family of 4.Italy 18days(Rome,Tuscany,C.Terra,Venice): accommodations

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Family of 4 with 2 teen girls traveling from Oregon to Amsterdam for 3 days & mainly Italy for 18 days. We have yet to arrange any accommodations and plan the trip. Husband is a museum and art enthusiast so he wants time in Florence and Rome. On the other hand, wife prefer the quieter pace of the hill towns. With 3 weeks, we can do both. I need help with specific accommodations and suggestions with our itinerary.
June 16 direct Pdx to Amsterdam, spend 3 days there with first day of recovering from fatigue. Where to stay?
June 20 early flight from Amsterdam to Rome.
July 9 early flight home from Venice via Amsterdam.
We don't need a car in big cities of Rome, Florence, Venice, and Cinque Terra. Will plan to rent a car in Tuscany.
Amsterdam 3 days, Rome 4-5 nights, Tuscany and Florence 6-7 nights,Cinque Terra 3 nights, Venice 4 nights
Here's our tentative itinerary.
Day 1-3:(6/17-19) Amsterdam: Canal Boat Ride, Anne Frank House,museum. Need place to stay for 4 of us.
Day 4-8:(6/20- 24) Fly to Rome & stay 4 nights.Get Rome Pass.Where to stay?
Day 9-14.(6/25-7/1) Rent car for 1 week in Tuscany 6nights with a pool. [b]Where to base our stay?[/b] Plan to spend 2-3 days in Florence. Plan to visit hill towns Sienna & others
Day 15: (7/2) Train to Pisa, Luca on way to C. Terra
Day 16-18:(7/3-7/5) C.T. Village hikes, Where to stay for 3 nights?
Day 19- 22:(7/5-7/8) Travel to Venice. Train vs Car? Where to stay in Venice.
Day 22(7/8)Venice Stay at airport hotel to fly back home on early flight 7/9.
Questions:
1. Suggestions/ changes to Itinerary?
2. Should we plan to visit another town?
3. Where to stay when exploring Florence and Tuscany hill towns. I will probably like this part of the trip the most when we are out of the busy major cities. Find a place with a pool. Stay outside of Florence?

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