In the case of the medieval walled town of Monteriggioni, a picture is definitely worth a thousand words.
Begin appreciating this tiny town, surrounded by vineyards, during the approach. After entering its walls there really isn't that much to do: visit the wine tasting room for a sample of some very (very very!) local wines; visit the museum or the church; sit in the main square, or piazza and soak it up; or mail your postcards from the one mailbox in the town.
There is no train to Monteriggioni, so arrive by car, and park for free at the bottom of the hill. It's off the beaten track but still fairly well visited by tourists, as well as the odd pilgrim, since it sits right on the Via Francigena, the pilgrimage trail from Canterbury to Rome.
One of my favorite spots to eat in the area is La Bottega di Lornano in the small town of (where else?) Lornano, a few minutes away by car. And my all-time favorite hotel in Italy is pretty close to here, too, La Locanda dell'Amorosa.
It's one of those places that makes you relax, sit back, and say "ahhhhhhhh".
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