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Tuscany base in May for 2 weeks with an 8 year old

We are spending a 2.5 month sabbatical in Europe this spring with our 8 year old. Current plan for Italy is:
1. 4 nights Rome
2. 3 nights Naples (to see the start of Giro d italia , Pompei, Capri if time)
3. 1 week Sicily
4. 2 weeks in Tuscany
5. 2.5 weeks exploring Lakes region/Dolomites in a camper van

Any suggestions for a smaller town base in Tuscany (ie not Florence) where we can chill out a bit but still be able to day trip or overnight some place interesting ( for example, hike in the hills or a day or two at the beach if warm enough in late May)

We are thinking about Lucca as a base for 2 weeks? Any other towns that you can suggest?

Another option is a week in Lucca and week near Siena in an agriturismo.

One of greatest concerns is keeping our 8 year old from getting bored.

Any suggestions/thoughts?

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