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One day with teens - Florence or Tuscany?

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My family including teenagers will be traveling from Venice to Umbria in June. We will be staying at a villa in Umbria for one week. Even though we have a week in Umbria, I would like to utilize our travel day as a tour day also. Since we will already be up and going I thought it would be best to make the most of this day and reserve an extra day in Umbria for relaxing/slower paced day.

My plan is to take the morning train from Venice to Florence arriving at 9:30 am. Then we have two options:

1. Be picked up in Florence by a private guide for a day trip of Siena and maybe San Gimignano, Monteriggioni or Volterra. Drop off at our villa in Umbria at the end of the day. Since we are staying in Umbria I thought it might be nice to see some of these towns of Tuscany while we are closer in the area.

2. Store our bags at the train station in Florence. Do a morning guided tour and explore on our own in the afternoon. Train or private driver to Chiusi in the early evening.

I would love feedback on which option might be best given our itinerary, schedule, etc. If we don't do Florence on this travel day we will probably visit Florence later in the week but would have to hassle with the train again. We could also visit Siena later in the week on our own, but don't think we would venture all the way to San G or Volterra.

Thoughts/recommendations?

Thanks

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