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Need help with Rome-Florence itinerary.

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Hello
I am planning a first time trip to Paris and Italy with my 20 year old daughter at the end of July/beginning of August. I have spent a lot of time researching the itinerary and would love some help!

Here's the plan so far:
Fly from California to Paris, spend 4 nights
Fly from Paris to Venice, spend 2 nights
Take the train from Venice to Florence, spend 5 nights
Take train from Florence to Rome, spend 5 nights (fly home from Rome)

My questions are:
1. Does the split of days between cities look ok? We enjoy great food, wine, shopping, exploring, probably more interested in historic sites than art, also looking to relax-not run from exhibit to exhibit. Prefer smaller towns to big cities, but we hear Rome is great, so want to explore it and the historical sites. We are really excited to do day trips to Tuscany!
2. We want to visit towns in Tuscany. Is it better to just have Florence be our base and do day trips to Tuscany? If we want to enjoy great food, wine and scenery-would it be a good idea to do day trips by bus from Florence to Chianti, Siena, etc. or rent a car and explore the beautiful towns ourselves? Is renting a car expensive, or a hassle-is it hard to drive there? Or since we are heading to Rome from Florence, should we visit the Tuscany area on our way to Rome? So many options!
3. I keep reading about paying cash for hotels for a discount. Is this advisable? I would love to get the discount, but how hard is it to find ATM's and get cash out multiple times during the trip?

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