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3-Day Tuscan Countryside: Itinerary ideas, suggestions ...

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Hello Everyone!

There are just so many amazing places to visit in the Tuscan countryside that I am having an absolutely difficult time with an itinerary.

Any suggestions/tips/insights from fellow travelers are welcome!

Background: My fiance and I (late 30s) are renting a car on our last day in Rome and would like to spend 3+ days exploring the Tuscan countryside on our way to Florence. We will be traveling around November 30 I prefer one central lodging location as a base for the 3 days but am open to suggestions.

Likes: Wine, wine and more wine, food, food and more food, scenic vistas, atmosphere

With that out of the way ... Here are some of the cities that interest me but clearly there are too many on my list for such a short trip.

Any help narrowing it down would be so appreciated and, of course, any specific driving itineraries involving wine and/or food tastings would be even better.

In no particular order:

Lucca
Ravenna
San Gimignano
Volterra
Siena
Orvieto (this would be a stop outside of Rome on our way to Tuscany)
Cortona
Montalcino
Montepulciano

I had originally thought about staying in the Montalcino area but thought that Siena may be more central. Any thoughts?

Any two cities that are similar? Have I missed and musts!

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