After our first day exploring Volterra and its stunning surroundings, we continued our Tuscany travel adventure by visiting the charming towns of Colle di Val d’Elsa and San Gimignano, discovering hidden gems and breathtaking views across the Tuscan hills.
A croissant and coffee gave us a quick start before heading to Colle di Val d’Elsa, a town I had never visited before… Nestled in the Elsa Valley, halfway between Siena and Florence, this hidden gem is still surprisingly underappreciated—even among locals. The town is divided into two parts: Colle Alta, the medieval upper town, and Colle Bassa, home to the famous Crystal Museum.
We parked just outside the old town and crossed a stone bridge that led us into the historic center. Narrow cobbled streets, stone houses, and sudden views of the Sienese hills created the perfect setting. As we wandered, we stumbled upon something unexpected—wine windows (buchette del vino), just like in Florence. My friend Isabelle and I turned it into a game: who would spot the next one first? We found eight in total. Sadly, none are in use today, but the winner still earned a well-deserved glass of wine in a nearby bar.
One of Colle’s most unique features is the panoramic lift carved into the rock, connecting the upper and lower towns through a tunnel. It’s the most scenic way to reach Colle Bassa. Unfortunately, the Crystal Museum was closed during our visit, but it gave us the perfect excuse to return one day. Colle Alta, with its quiet streets and lack of crowds, felt like discovering the most authentic side of Tuscany.
From there, we continued to San Gimignano, famously nicknamed the “Medieval Manhattan.” Its towers dominate the skyline even from afar. In the 13th century, the city boasted 72 towers—today only 14 remain, but they still define its iconic silhouette. The town was bustling with visitors, but we couldn’t leave without stopping at the legendary Gelateria Dondoli, often hailed as one of the best ice cream shops in the world.
Our day ended back in Volterra, where we enjoyed a delicious porcini risotto paired with a glass of Chianti before climbing the Palazzo dei Priori tower. Built in the 13th century, this was the first town hall of its kind in Tuscany and later inspired Florence’s Palazzo Vecchio. From the council chamber, we climbed up to the belfry (hoping the bells would stay quiet while we were there). The view over Volterra and the surrounding countryside was simply breathtaking.
Before heading back, we visited the Sant’Agostino Church, where the Diocesan Museum of Sacred Art surprised us with its richness. Ancient reliquaries, alabaster treasures, and rare miniature choir books made it an unforgettable stop—yet one that most guidebooks completely ignore.
It was a full and rewarding day: an underrated medieval village, a world-famous tower town, and the timeless charm of Volterra all in one. We ended with a glass of wine at a local bar, already looking forward to day three—which would even include a night at the theatre.