Our First Taste of Tuscany: Montelpulciano, Montisi, and Pienza

This is where our official journey in Tuscany begins, starting in the Chianti region, an area many people envision when they hear the word “Tuscany.” With its sand-colored hills dotted with vineyards and fortress-surrounded medieval towns, you feel as you have entered another era.

We arrived in Tuscany after our Southern Italy excursion with a pit-stop to pick up  our dog, JoJo, who was being cared for in Rome while we were away. We headed to the town of Montelpulciano for a one-night stay, a medieval and Renaissance hill town that is world-renowned for its wine. It is also a producer of pork, cheese, pici pasta, lentils, and honey.

We booked an apartment on a farm about a kilometer from the town, thinking it would be an ideal place for JoJo to run around. It was tucked away on a gravel road hidden from the street, and after several attempts of stopping, turning, and looking around, we finally located the property. We were greeted by a mother and daughter who ran the guest accommodations located next to the their Tuscan home. We were welcomed with a bottle of wine grown in their vineyards.

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View of the vineyards from our room

We decided to take a walk to explore the town, which required a strenuous up-hill hike up the road to reach the walls surrounding the city. We were immediately struck by beauty of the town, so flawless in its preservation that you felt like you took a step back in time. The town was also a car-free zone, which added to its allure. We rambled through the narrow streets, taking note of how people must have lived in this city centuries ago. It was also not as crowded as some of the other medieval towns we would explore such San Gimignano and Siena, but this could also be because it was later in the evening. The one thing about these towns that can be somewhat disheartening is that they look like museums rather than a place where people live. The only locals we could see were those running the shops. So in some ways it would not feel as authentic as say, walking to less- immaculately persevered town a couple of kilometers away. Regardless, we had already made up our mind that we would joyously welcome Tuscany as our new home.

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Because I had done my research for dinner, we made reservations at Osteria Acquacheta, apparently an institution in Montelpulciano. We could tell it was going to be good by the crowds of people waiting outside the door. It is a shared dining experience, and so we ended up sitting with a young Austrailian couple drinking and dining their way through Italy. We were somewhat relieved to be able to speak with native-English speakers freely again. But the good company was only half the experience. The food was a excellent and I would 100% recommend anyone in Montelpulciano to dine at Osteria Acquacheta. The meats and cheese were to die for- certainly the most flavorful we had tasted so far in Italy. The pastas were only better. such as the gnocchi was sautéed in olive oil, garlic, and red pepper flakes.  We were also introduced to our now favorite pasta called pici, a sort of thicker-textured tube like spaghetti. This pasta is not easily accessible in the U.S., and with the duck ragu the dish was elevated to another level. We also got the local specialty, Florentine steak, a T-bone sourced from the Chianina cattle in Tuscany. It is seasoned with salt, pepper, and olive oil, grilled, and served “bloody.” Although the steak was very good, I am not a big fan of T-bones in general so I could only say so much. Ryan, on the other hand, was enamored with it. After our meal,  we decided we much preferred the food of Tuscany over that in the South, which was primarily dominated by seafood.

Before heading off to Northern Tuscany, I coaxed Ryan into taking a hike through the Crete Sensei, an area of the Tuscany consisting ranges of hills and woods outside of the village of Montisi. I had a trail map in my guide book, which laid out what looked like a leisurely morning walk. Oh, we were wrong. The first hour was quite enjoyable. JoJo in tow, we strolled through an off-road path along farmland. At one point in the trail, the book insisted we heed right into a thicket of trees. I said, “let’s go, it’s probably really nice down here!” We ended up hiking through an unkempt path through the woods, with thorns and mosquitoes nipping our legs at every corner. And what we thought was a ten minute walk ended up being a half hour, with a steep uphill incline. At the top of the hill, we met the farmer whose land we were walking by (apparently named Giueseppe according to our guide book). We talked to him about JoJo for awhile, since most Italians have never seen a dog so white as snow. We managed to exchange a couple of friendly phrases in Italian before heading off. From this point on, we were always amazed at how friendly local Italians are, especially in Tusany.

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About an hour later, we reached the abandoned farmhouse marked as a stopping point in our guide book. Still quite preserved in its original form, it looked like a scene out of movie, with the endless lunar fields in the background. At this point, we were still about two hours from our starting point of Montisi. We were running low on water, and Ryan and JoJo were starting to complain. At this point, however, we had no choice but to carry on. Another 45 minutes in, we started to hear a frenzy of dogs barking as we approached another farm alongside the trail. They were clearly directed at JoJo, who mistakenly took the threatening barks as an invitation to play.  The farmer then approached us and said that this area was not safe for JoJo, as his dogs were trained to attack. To our luck, he hoisted us on the back of his pick up and drove us almost to the end of the trail, chopping off about 30 minutes from our journey. Let us say we were very grateful for the kindness of strangers that day!

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Exhausted, we walked the remaining mile and a half along the road back to our car, where we set off for the town of Pienza, a Unesco heritage sight. I read about a restaurant owned by an older couple in one of the smaller piazzas called Ristorante Rossellino. We shared a buffalo mozzerrella salad, followed by another pici pasta with ragu and a pici with pesto sauce. Both were satisfying and a delicious reward after our hike. The owners also loved JoJo (starting to become a trend now…) and ended up talking to us for a half hour about their restaurant. By the end of the meal, we were fast friends and would be welcomed back graciously. Unfortunately we did not have enough time to thoroughly explore Pienza, but could immediately tell it was another medieval fairy-tale-like town stuck in time. It just provided more of a reason to return.

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