Monday, September 22, 2025

Via Francigena Days 30 and 31: San Gimignano to Monteriggioni & Monteriggioni to Siena

Thursday, September 18th

It was a beautiful day leaving San Gimignano with very few clouds in the sky and a weather forecast of 80+ degrees, promising a hot day of walking. We had two route options and, based on reviews we read online about this stage, chose the more scenic route, which also happened to be a couple miles shorter than the route we were originally going to take. We walked through vineyards, olive orchards and along forest paths, crossing the Elsa River via large boulders. After a long uphill climb into the town of Strove, we transferred via taxi to the hilltop town of Monteriggioni, a perfectly preserved medieval fortress town. Even our lodging for the night is reminiscent of the town’s past as it was once the fortress prison. Thankfully, our rooms are above the old prison and have been beautifully refurbished. All told, we walked 13 miles today with 1400 feet of elevation gain.

Morning mist on the hills outside San Gimignano







One last view of San Gimignano

Tuscan vineyards and cypress trees








Making our way across the Elsa River







Entrance to Colle di Val d'Elsa's old town

Old cell block door on the ground floor of our
accommodations







Monteriggioni's town plaza








Wandering the streets of medieval Monteriggioni










Friday, September 19th

Another hot day in the Tuscan hills, but thankfully we spent the first portion of the day walking on shaded forest trails or through recently plowed farmlands. We also passed a few medieval castles, most notably the Castello della Chiocciola, which is thought to have been built in the 14th century and is remembered for the heroic stand of its defenders, who combatted invading troops in 1555.

The last quarter of our trek was spent navigating the long uphill climb into Siena. Our walk from Monteriggioni to Siena was 12.75 miles with 1450 feet of elevation gain. We had a late lunch in Siena and then spent the remainder of the afternoon trying to do our laundry. The first place I found on the internet had gotten terrible reviews so we didn’t even try it. The second place only had 2 washers and dryers which were all in use and had people waiting. The third place was closed due to a fire. Since those were the only laundromats we could find within a 2 mile radius we decided to head back to the hotel and admit defeat. Once there, Becky asked the receptionist if she knew of any other laundromats and she referred us to one that had recently opened. Eureka! We now have clean clothes and even had a bit of excitement while at the laundromat. The Italian General Confederation of Labor (CGIL) called a nationwide strike and rally today to express solidarity with Gaza. The Sienese rally (at least 1,000 strong) passed by the laundromat waving Palestinian flags, carrying banners that read “Stop Genocide” and chanting “Free Palestine”. It was quite the sight!

One last view of the walled town of Monteriggioni







Walking buddies

Castello della Chiocciola













Making our way toward Siena


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