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Choosing a base in Tuscany for a return visit...

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Hello everyone --

It's the age old question, but please bear with me. I have been to Montalcino, Pienza, and Montepulciano and loved what I saw, smelled (especially in Pienza), and ate. For a return trip this May, I'm hoping to visit another part of the region. However, I am having a hard time adjusting to the idea of doing so because I'm not certain about how crowded it will be, or if the scenery will be as satisfying.

Here are our options thus far:

Base in San Gimignano w/day trips to Volterra, Monteriggioni, Siena
or
Base in Cortona; day trip to Assisi and revisit Pienza/Montepulciano

General thoughts: we're looking to relax, take photos of the landscape, and eat great meals. I should also note that we enjoyed the intimacy that Montalcino offered us as a base during our last Tuscan journey.

Thanks in advance! I look forward to reading your thoughts.

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