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Tuscany's Wine Towns: Pienza, Montepulciano, Montalcino

Tuscany's charm can't be denied. While its landscapes of green and gold can easily draw you in, these medieval villages and towns perched on tops of hills surrounded by vineyards are an integral part of that charm. All three towns listed below will enchant you with their Tuscan architecture in narrow cobblestone streets, beautiful views of the countryside below, and a large variety of delicious (mostly red) local wines. Pienza, Monetepulciano, and Montalcino are all located in the Siena province of Tuscany, in or near the Crete Senesi region. It is relatively easy to walk around each village in a matter of an hour or two..of course you may need more time if you stop in one of the Enotecas (wine tasting rooms). If you also plan on stopping at any of the surrounding vineyards and wineries for a full wine tasting, I highly recommend calling in advance to make a reservation.


Smallest of the three towns, Pienza is known as "the ideal city of the Renaissance." Pope Pius II transformed his birthplace village into what he considered the Utopian city it should by blending together principles of classical times and the great Italian Renaissance. Pienza is also known for the delicious Pecorino cheese that comes from the area. The Southwest part of town near Duomo di Pienza offers breathtaking views of the Val d'Orcia Valley below.

Montepulciano A medieval town on top of a large hill with beautiful views from all sides of town, Montepulciano is best known for its Nobile red wine. Piazza Grande in the heart of town is a place where many events happen, including the Bravio delle Botti race which consists of pushing large wine barrels uphill through town. The Bravio takes place every year on the last Sunday in August.


Wine lovers may recognize the town's name as part of the name of the prestigious "Brunello di Montalcino." Another beautiful hilltop town with amazing views, adorable streets, and bold full-bodied wines. A glass of Brunello di Montalcino is a must if you are visiting the area. Finding a good happy hour deal or just buying a whole bottle will likely be your best bet as this one tends to be more expensive than most other wines in the region. Happy hour typically also means you get to snack on some free appetizers such as local meats, cheeses, and dips!

BONUS: Montisi - a hidden treasure Not a touristy location or a particular wine region but just a gorgeous, traditional village to see. We are so grateful to our Workaway hosts Camilla and Tommy for showing us this treasure and for letting us participate in the amazing local luncheons and dinners during the Giostra di Simone festivities.

The power to decide, the power to choose from life's menu of possibilities is in itself the seed of creativity from which infinite ranges of new waves of potential arise. When you make a decision to do or not do something, you are not only deciding for yourself but affecting many parts of all of existence as we float through this interconnected web of love we call humanity. The action of one wave inevitably changes the expression of the whole ocean. We are that wave in the ocean of humanity.


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