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Italy itinerary help - beyond the basics

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Hello! I will be traveling with my husband and four year old son to Italy for 3-1/2 weeks in mid-September. We will be flying into Florence and out of Venice. We will be renting a car and like to stay in country places with swimming pools when we are not in cities. Since we are traveling with our son, we like to rent 2 BR places with kitchen, dishwasher, washing machine etc.

I am looking for suggestions on the itinerary and specific places to stay. We have been to Italy a few times before (including getting married in Chianti and honeymooning all over) as well as a trip to Orvieto, Lucca, Rapolono di Terme, and Viterbo about 2-12 years ago.

Thanks so much for any input into the itinerary.
Here's our potential itinerary:
Sept 12 - Arrive Florence. Stay Fiesole or somewhere country-ish with pool within one hour of Florence Airport. Or possibly stay in Florence itself.
Sept 17 - Stay somewhere in Umbria or Marche as home base for area.
Sept 24 - Bologna (or other suggestions - visited Mantova in the past and really loved it!)
Sept 27 - Lake Garda or Lake Como
Sept 30 - Verona (thought it was really delightful when we visited in the past)
Oct 2 - Venice for five nights

A few questions:
1) We are considering staying in Fiesole when we first arrive as a base for visiting Florence. We are thinking it will be more relaxing than staying directly in Florence. Other suggestions for cute towns or specific places to stay about one hour from Florence airport?
2) Suggestions for specific neighborhoods or apartments in Florence (need 2 BR with lift preferred)
3) Suggestions for specific towns or places to stay in as a base in Umbria or Marche. What do people think of Spello or Spoleto?
4) Is Lake Garda worth a visit? On our honeymoon, we visited Lake Como and stayed in Bellagio which was delightful. But since we are going to Venice, I'm thinking that Lake Garda would be easier.

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