Last April Marco and I went with two friends on a weekend road trip. The first road trip we went on together was from Milan to Umbria, in a weekend tour of just a small part of the region. This time, we decided to tour the Val d’Orcia region in the south of Tuscany. The region is characterized by the dozens of beautiful, characteristic wine-producing towns. Towns that are so beautiful and (agri)culturally important that in 2004 the entire valley was included on the list of UNESCO’s World Cultural Landscapes. 

Each town is so small we were able to make multiple stops, sometimes touring one town in a half an hour and sometimes lingering for half a day. Though it was a lot of driving, the views – and food – more than made up for it!

Of course a weekend is never enough to delve into a culture or learn the intricate rhythms of the town, it is usually enough for us to disconnect from work, take deep breathes and enjoy each moment of our trip. From the pilgrims who had just reached their first stop of the day in Buonconvento to the myriad cyclists we passed – solo, in groups, taking it slow or participating in a race. We joined a town barbecue in Montalcino, tried some wine in a reproduced castle, stayed in a beautiful Airbnb home surrounded by the owner’s family in Siena, befriended countless cats and filled up on enough pici with ragù to hold us over until our next visit.



Our first stop was Arezzo. Not quite in Val d’Orcia yet, but we had to have dinner somewhere! 



Have you ever seen Life is Beautiful? The setting was in Arezzo. That’s where the main characters lived before the war.



Everywhere you turn in Italy you can find romance.



Olive trees and vineyards line the hill leading up to Montalcino. Here, the Brunello di Montalcino red wine reigns.



The entire town is just 94 square miles, but it’s filled with the type of “every day scenes” (only in the most beautiful surroundings) that you travel all the way to Tuscany just to see!



like this one



or this one…



…or this one!



The view from Montalcino, which, like nearly every Tuscan town, sits atop a hill.



vineyards vineyards vineyards



We were lucky to escape Lombardia’s cool rainy weather to enjoy Tuscany’s warm spring weather!


Our original plan was to head from Montalcino to Montepulciano, another one of those famous wine towns, before we ended the day with dinner in Siena, but we decided to cut the drive time in half and stop in Pienza instead, whose town square is a UNESCO World Heritage Site. Good thing we did! At just 47 square miles, it’s even smaller than Montalcino, but had a whole lot of personality. The town was clean, well-preserved and friendly despite the swaths of tourists (including us!). After a long winter, I particularly enjoyed the flowers.


like these flowers!



Style and cats in the heart of Pienza



The Pienza Duomo


Finally, we were able to visit Siena. Though I’ve been multiple times from my time studying in Florence, my Italian husband had yet to see the incredible city even once! We first went for Saturday night dinner, where we split a cheese plate and mixed crostini. Side salads were just for the illusion of health as we split a nearly 3 pound Fiorentina steak. A must while you’re in Tuscany, this massive T-bone steak is, like it’s name suggests, a staple of tourist food in Florence. Outside of the popular city, however, the taste is the same but the cost is usually much less!

After dinner we grabbed some beers and headed to Piazza del Campo, the center of the city and where the Palio horse race is held each year. It seems the Piazza is perpetually filled with people. During the day, tourists fill each inch of the shell-shaped square. This night, it was absolutely filled with people listening to a small group of street performers, singing, dancing and drinking. I had never been to the city at night, and enjoyed a completely different atmosphere than the usual day-tripper atmosphere I had grown used to.

We did get to see the city during the day, returning Sunday morning for a last walk through the red brick town before heading home. It was just a taste for Marco – we didn’t climb the Torre di Mangia or even see the inside of the Duomo (it was closed), but like I said, you can only fit so much in a weekend trip! Sometimes, that amount is more than enough.






Piazza del Campo with the Torre del Mangia to the right. 



How about having one of those as an apartment?

Halfway through this trip I elegantly dropped my camera and blocked the lens, meaning the photos I was able to take were often out of focus or too far away, since zoom or even moving closer and refocusing were both out of the question. I tried nevertheless, and continued taking picturess on both my semi-broken camera and my smartphone. That said, the trip was about friends and food (as are all of our weekend trips) and we enjoyed plenty of both!


You might also like:
My Favorite Foods in Tuscany and Umbria
Colle Val d’Elsa, Tuscany’s (Relatively) Hidden Gem

A Road Trip in Friuli Venezia Giulia

Written by ginamussio


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