The Maremma and Hidden Gems in Chianti

During my mom’s visit to Italy we took a road trip to the Maremma region of Tuscany, an area that is often overlooked by tourists for the more popular Chianti and Val d’Orcia. Although the landscape can be described as rolling hills, it has a more wild and “unkempt” quality compared to the seemingly manicured areas of the Val d’Orcia. The region is known for agriculture (Italian milk and yogurt often come from Maremma), its cowboys and wild horses, protected parks for wildlife, thermal pools, seaside, and cities made of Tufa rock. There was certainly enough to do to to keep one occupied for a week, yet our trip was only limited to two nights.

Our first stop in the Maremma was Massa Marittima, a quiet medieval village situated on a hill. It’s architecture was similar to other medieval Tuscan towns such as San Gimignano and Volterra. It is also separated into a new and old city by a looming bell tower and fortress. The village had an interesting cathedral in the main piazza that was built on a side angel.

The streets then sloped upwards towards the bell tower. I climbed a narrow, steep ladder before hitting the next platform of the fortress. it was so tiny that I could barely fit, and I am a small person! I then scaled several sets of winding staircases before reaching a door opens to a stunning panorama of the countryside. A couple flights higher led me to the bell tower and a 360 degree view of the Maremma.

Although the tower was the main attraction, the town had a quaint, relaxing atmosphere after a long drive. We were among few tourists and the shops, although geared towards visitors, were charming and unique. Our favorite was a store selling hand-painted bags. The artwork was exquisite, and it felt like we were walking through a gallery. For such beautiful bags, the prices were reasonable and my mom bought an adorable purse painted with the local flower “papa vero.”

Our bed and breakfast, Country Resort Guadaloupe, was located about thirty minutes away in the countryside. The apartments were tastefully decorated in country style and had a view of a hilltop village which was beautifully lit up at night. We enjoyed a peaceful breakfast the following morning next to the owner and his family. They were very gracious to hear how much we enjoyed our stay and how well they accomplished the feeling of “letting go.”

Our next stop was Pitigliano, one of villages in the Maremma famous for being built on Tufa rock and its Jewish history. When approaching the town, you are greeted by a breathtaking sight of a city built on tufa. The pictures do not give the moment justice. The experience was otherworldly, it was reminiscent of a ruin or of a city that was destroyed in a war. Yet, reminders of life were evident by lights, hanging clothing, and the occasional parked car.


We hired a tour guide,Elisabetta, who met us to the entrance of the old town. We learned the Etruscans built the city out of Tufa Rock because it is very malleable. Over time, the buildings deteriorated and the city was rebuilt in medieval style. The city belonged to the Orsini family from the Aldobrandeschi family, and eventually passed to the Medici family in Florence until Italy was unified as a country.

Much of the main piazza was destroyed during WWII and had to be rebuilt. Most people visit the ancient Jewish quarter, which at one time had one of the largest Jewish communities in Italy after the Pope banned the Jews from Rome. They arrived in Pitigliano because the Orsinis allowed Jews to work and live where they pleased, and they offered artisanship in a town filled with farmers. The Catholics and Jews had a thriving community and lived symbiotically for many years. When the Medicis came to rule, the Jews were forced to live on one street, or the “ghetto.” This was where the synagogue, matzo oven, butcher, mikvah, and other elements of Jewish life existed. The area is now a museum. One interesting little fact is that the Jewish people created a pastry called the “sfratto,” meaning eviction. It was supposed to represent the government knocking on the doors of their shop reminding the Jews to return to the ghetto for the night. The sfratto was thus created to make something sweet out of unfortunate circumstances.It is has a hard cracker-like shell on the outside, but is filled with a mixture of nuts of honey on the inside.

Unfortunately, there is only one Jew left in the town, as most left for other places after Italy was unified. However, the Jewish connection remained strong here. During WWII, the Catholics hid the Jews of Pitigliano in their homes, and not one was killed. The only Jews from Pitigliano that died were the ones that left the town and a memorial for them exists today. The families that helped the Jews received a Yad Veshem award.

In the 1970’s, the old synagogue collapsed. Even though the Jewish community no longer existed, the town rebuilt the synagogue and made the Jewish quarter a museum to pay tribute to the Jewish history of the town.

The museum was particularly touching. Inside you can visit the mikvah, wine cellar, kosher butcher, and room where matzo was made. Many of the rooms are underground since The Jews were restricted to one street and had to built down- literally into the old Etruscan ruins. These elements of Jewish life in Tuscany were fascinating, and the town takes great pride in educating the public on Jewish culture. The last remaining Jew in the town, Ms Elena Servi, founded the little Jerusalem foundation to help keep this spirit alive.

Overall, we loved our visit to Pitigliano. Even thought it’s Jewish history was of special interest to us, the town is of unusual and diverse character, especially after visiting many Tuscan towns with such a Catholic focus. It was no doubt the highlight of our trip.

Our second night was spent at a rural agriturismo called Poggio al Tufo about 20 minutes outside of the walls of Pitigliano. The agriturismo was actually apart of a larger vineyard and was situated on a beautiful property overlooking the landscape. The agriturismo had its own restaurant serving up local specialties, including my new favorite soup, aquacotta. It is the Maremma region’s version of ribolitta. The difference is that bread lines the bottom of the bowl and an egg is poached on top. The broth is a thick consistency of spinach, potatoes, carrots, and whatever else is in season. I loved it so much I had it for both lunch earlier in the day and at dinner!

We had a later start the following morning to purposely relax and enjoy the surroundings. Our initial plan was to visit Montalcino before heading to Colle di Val d’Elsa. Since it was out of the way, we decided to take a more direct route, which nonetheless took us through the Val d’Orcia. The lanscape noticeably different in the Val d’Orcia. It is manicured, lined with cypress trees and different vegetation- more of the quintessential picture of Tuscany, and remarkably breathtaking. The roads were more windy and graced through the hills. At our much needed bathroom break, we came across a small village called Radiofani, in the center of the Val d’Orcia. The town is not frequented by tourists, as there was only one restaurant and the only other stores being butcher and local grocers. The buildings were made of stone, and the preservation rivaled that of San Gimignano. We spent a half hour meandering the narrow alley ways, coming across surprised a like this adorable piazza- which coincidentally was the area where the Jews used to live in the town.


We dined at the town’s only restaurant, indulging in a hearty Tuscan bean soup and mushroom soup. The soups were served in large metal serving bowls for sharing. I thought aquacotta was amazing, but this Tuscan mushroom soup was among the best I’ve had in Italy. And it only consisted on puréed vegetables and olive oil. It amazes me how the Italians can create such hearty soup without the use of cream, as is usually the case in the U.S.!

At the top of the town lies the ruins of the town’s old fortress and a cemetery , overlooking a serene view of the Val d’Orcia. This town, although unplanned, was another hidden gem we embraced on our journey.


As we approached Colle di Val d’Elsa, the roads became noticeably more crowded and the landscape less picturesque (this is relative of course, because the area is still beautiful!).We were also closer to the main Tuscan destinations of Siena and Florence which were approaching the beginning of high season.

We stopped in Colle di Val d’Elsa because I had read it was worth visiting in the area and was on the way home. However, we were somewhat disappointed with the town. It was similar in style to many of the medieval towns in the region, but was not preserved as well, and had a grittier, more urban feel to it. There were also no major sights or charming piazzas to stop and have a coffee. It also lacked a variety of shops except of those selling crystal and glass, for which the town is known. Needless to say, after a lengthy walk though (the town was very long), we had no desire to stay nor to return.

Our visit to Colle di Val d’Elsa was redeemed by our accomodations at the Hotel Villa Sabolini. As the name suggests, it was a country villa turned hotel . The hotel was split into three separate houses – which I am assuming were the main house and guest houses in earlier times. Although parts of the building was in need of renovation, the grounds boasted a lovely garden, pool, and outdoor dining area. I think JoJo enjoyed his stay the most, as he and the hotel, a massive St. Bernard (who was only 11 months old), played for hours. I had never seen a dog this large in Italy, and it was the definition of a gentle giant. The dog was slow and lethargic in its movements, and at only 11 months was so obedient it did not dare disobey the hotel staff. If only Jojo did not have such a mind of his own! The following morning JoJo was so dirty one of the hotel staff helped me wash and brush him before we left. Villa Sabolini was definitely a winner in terms of hospitality and service!

We ended our trip with a few hours in Florence for my mom to pick up some leather gifts. The city was congested and difficult to navigate- making me long for the times when the city was quieter. regardless, I am glad we got our peaceful fix in the unexplored Tuscan Maremma.


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