You may include in your tour Pisa (Piazza dei miracoli), Lucca, Pitigliano, Volterra.

Driving but especially parking in Florence is not easy especially in the center where some areas are not accessible to cars. Outside the town is generally easy, roads are good and June is not yet the peak touristic season therefore in the small towns parking should be easier.

If you can modify your reservation it may be better to find an accomodation out of Florence for the days you want to visit Tuscany.

You might want to look at Tau Touring (based in Lucca). We've had such grand luck with repeated booking with this group and I believe they have a vehicle that would accommodate your group. They will supply a van and driver.....but you'll find that their driver are so well-versed and hospitable that you don't need an additional "guide".

Oops.....should be driverS (....are so well versed).

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