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With a reputation for being one of the most beautiful “hill” towns in all of Tuscany, Montepulciano, like Montepaone and the The Frazioni of Montelupone, offers authentic Italian charm, the kind that you won’t find at more tourist trappy locations. The façade of the Church of Saint Agostino is all that remains, but, along with the ruins of Oratorio della Misericordia, Montepulciano is a wonderful place for anyone looking to get a look at ancient architecture.

We absolutely must recommend booking ahead. The town is relatively small, and can become quite packed during tourist seasons. There are certainly some cheap hotels in Montepulciano to be found, but if you don’t book ahead with a site like EasyToBook.com, you may wind up having a hard time finding any vacancies. Finding discount hotels in Montepulciano should actually be quite easy, in fact, it’s finding Montepulciano hotels with a bed to spare that’s tricky.

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