Italy 2026 – Days 3 and 4
Day 3 begins our actual pilgrimage Jo on the Via Francigena, starting in Monteriggioni. Unlike the Camino de Santiago in Spain, which gets over 350,000 pilgrims a year, this trail probably gets less than 20,000 per year. As a result, the hiking is more rugged with almost no support stops. So, packing enough water is essential. That said, we did meet three other pilgrims at breakfast this morning – Mikhail and Angelica from Milan, and Larch from Scotland. All three were hiking two segments of the VF, the segments before and after Monteriggione. We met a few other pilgrims on the trail today who were doing the same thing. So, the two segments before and after Monteriggioni must be very popular segments in Italy.
As we started our 13-mile hike heading south away from Monteriggione, we could still see the outline of this beautiful fortress town for miles over our back right shoulder. And I imagined what it must have been like to have lived here in the Middle Ages and looking at that fortress miles away and thinking that it was the one place you could go to be safe. We would see many of these hilltop fortresses on our pilgrimage, but none as special to me as Monteriggioni.
So, we left this postcard perfect hilltop this morning with mixed emotions – sad to leave this amazing enclave, but also nervously excited to explore southern Tuscany on foot. We started walking among rolling hills and through dense forests past an abandoned medieval village and a few castles. After 10 miles we were tired from all the hills, but we decided to take the small detour to the Hermitage of San Leonardo at Lago. When I think of a hermitage, I think of a small building. This place was anything but small. It was an imposing structure.
To enter the grounds of the Hermitage and the worship space, we had to ring the local friar, who let us in through a locked gate. At one time, this place was a self-sustaining and thriving religious community. Now it is almost abandoned. No one else was there but the friar, Davis and me. It was a special visit.
After another few miles for a total of 13 miles for the day, we arrived in Siena. A World Heritage site, Siena is a town well-known for its Palio horse race which occurs twice a year. The next race was actually happening the upcoming Sunday! The city is also known for its medieval buildings including its stunning black-and-white striped cathedral and the wonderful Piazza del Campo, which is where we had dinner tonight.
We spent the afternoon walking around the town.Unlike any of the other towns we would spend the night in during our pilgrimage, there were many tourists. During the rest of our hike, would end up in small hamlets or towns where we would not see another tourist, much less an American!
I marvel at the people I meet on these trips. In addition to the pilgrims we met at breakfast, we also spent time with a young man from Winnipeg, Canada, an older gentleman from Switzerland, and a young Italian woman with her dog.
While in Siena Davis really wanted to visit the town Hall, where one of its large meeting rooms contains the famous frescoes, considered masterworks by Ambrosio Lorenzetti, which were painted around 1338. The Allegory of Good and Bad Government depict the visual contrast between a prosperous, just society and the devastating effects of tyranny and corruption, which seems very relevant in the our current environment. One creature that stands out in the good government fresco is a black and white pig. In the bookstore Davis bought a children’s book for James that describes that world from the perspective of the pig. I cannot wait to read that book to my grandson. We could have spent more time there. Siena may have been the first true democracy in the world. It would eventually be conquered by Florence and be ruled by Florentines.
But I have to share the following. While having a marvelous dinner with another wonderful server Davis and I met a gentleman from North Carolina, who also has Swiss citizenship. He was doing a Backroads trip with his wife and some friends. We got on the subject of Italian pizzas. He agrees with me that Roman Pizza is the best Pizza in the world. So, I cannot wait to introduce Davis to Roman Pizzas at the end of our trip!
The second day on the Via Francigena would be our shortest hike. After exploring Siena in the morning, we started our hike at 10 a.m. walking through farmland and rolling hills. The hiking today was not as scenic as the first day because much of our walking was on hardtop roads. After 11 miles we arrived at an imposing 14th century medieval building- the Grancia di Cuna. This fortified group of buildings served as protected storage for food supplies in the Middle Ages and offered hospitality to pilgrims and travelers. From there we took a transfer to the small village of Buonconvento, where we would spend the evening.
Today’s adventure was notable for three reasons. First, we did not encounter a single American in Buonconvento – and we encountered and spoke to several people. Second, we did not encounter another hiker on the entire trail today. Third, we encountered at least 50 cyclists. We found out why the next day.
This part of Italy loves its cycling. There is something called L’Eroica, which is a celebrated vintage cycling event held annually in Tuscany, Italy. The Race takes place in the Chianti wine country of Tuscany, where riders tackle white gravel roads through rolling hills and vineyards. The race requires participants to ride bicycles made before 1987, equipped with period-appropriate components. In other words, these are hardcore cyclists wanting to honor the history of the sport!When Davis and I arrived in BUONCONVENTO we stopped at a cafe/wine bar and sat outside and had some food and drinks. We had a server named Sophia who was originally from eastern Italy. She was amazing. She recommended a place for dinner where I had maybe the best liver pate I have ever had.
Almost everyone we saw while we visited Buonconvento were either locals or cyclists with a few pilgrims sprinkled in – not your typical tourist spot. And I loved it.
