Secret Tuscany

Villages That Escape the Crowds

Florence, Siena, and San Gimignano are must-visits when in Tuscany, but after living here for a while, I was curious to explore the lesser-known places, the ones not bound by tourism. Towns I could walk through, eat in, and have a coffee just like the locals. Places where only Italian is spoken, and the streets are deserted between noon and 4:00 p.m. Places where you don’t need a tour guide or a crowd to feel the magic of centuries past.

And so, I would get on my bike or drive to discover new places. Today, I’ll tell you about three of my favorite discoveries, three medieval villages that aren’t on most maps handed out at the car rental desk. Places I return to again and again, being less than 30 minutes away from my home. Villages frozen in time, not as museums, but as living, breathing communities. Without the hum of tourism, you can feel the heartbeat of the place.
You won’t find souvenir shops or Instagram crowds here, just narrow stone alleys, hidden courtyards, and a deep sense of authenticity.

Let me take you on a road trip to Casole d’Elsa, Mensano, and Radicondoli. If you’re coming from Siena or Florence, they’re about a one-hour drive away.

Casole d’Elsa, Mensano and Radicondoli, are a short distance from one another.

Casole d’Elsa

Casole d’Elsa is a picturesque hill town with Etruscan origins. It became an important medieval stronghold due to its strategic position between Siena and Volterra. In the 12th and 13th centuries, Casole was contested by the rival powers of Florence, Siena, and Volterra. Eventually, it came under Sienese control, and remnants of its medieval fortifications, including the castle and walls, still stand today.

Sculpture from I giardini di Nigel

Of the three towns, this is the one where you'll find a bit more art and culture, including sculpture exhibitions and an Etruscan museum. This town of fewer than 4,000 people has a coffee bar and two restaurants that serve Tuscan specialties. It’s a shame that the little bakery owned by Francesca closed down last year, as it was my favorite pit stop while biking. Their mortadella panino was out of this world.

My mortadella panino in Casole

Above clip is Francesca on her wedding day in Casole and there went my mortadella panino with it.

If history interests you, a visit to the museum is worthwhile. Otherwise, I suggest a private wine and olive oil tasting right across the street from the museum, on the town’s main road. You’ll be welcomed by Antje and her husband in their living room or on their terrace for a friendly and warm chat about their products. No sales pitch, just good conversation. You can book this at www.estevanwine.it.

Etruscan Museum

At Estevan Villa with my cousin Mike, His wife Liz and dear friends Gary and Sara

Private cantina

Oil olive from their last harvest

Back in the car, we wind our way through the hills and cypress trees toward Mensano, just 9 kilometers away.

Mensano

Mensano is a village so small you might miss it if you blink. If you’re lucky enough to find the church open, you’ll be rewarded with one of the most beautiful Romanesque churches of its kind in Tuscany. The small, neat streets and the quietness are immediately noticeable. It takes about 10 minutes to cover all the alleys, and if you walk up a few narrow steps at the very end of the village, you’ll be astonished by a view of the countryside, a postcard image of the Tuscany you've always dreamed of.

Romanesque church

I come here at times with a book and just sit for an hour or so.

Relaxing with a view

Typical street in Mensano

The calmness of evening

Lunch with friends Lou and Michelle at Il Carato

There are no stores, no souvenir shops, not even a coffee shop, but there is one great restaurant called Il Carato, recently renovated and worth the stop. Outdoor tables under umbrellas, a small menu, well executed. It’s a little flashier than the town’s humble charm, but sitting outside on a summer day, far from the crowds, tasting local Sangiovese and pecorino cheese… well, it doesn’t get much better than that. Always better to reserve if you plan to eat there. www.il-carato.com

From here, we carry on about 10 km west, where the hills grow a little wilder and taller.

Radicondoli

The little town of Radicondoli is perched some 530 meters high on the metalliferous hills west of Siena. Its history traces back to Etruscan and Roman times, but it flourished in the Middle Ages as part of the Republic of Siena. The town was known for its wool production, and later, for its geothermal activity, which is still significant in the area today.

Radicondoli has retained much of its medieval structure, with narrow lanes, stone buildings, and a peaceful, unspoiled character. I love strolling the side streets, it’s been kept as it was, and you can sense, by the cleanliness and the manicured flowers on window sills, the pride of the villagers. Here, you really feel the unspoiled everyday life of the local residents. As I walk the streets, I can feel people watching me, maybe wondering, “Who is he?” I can’t help but think what life must have been like 600 years ago, climbing those same steep, narrow paths.

Radicondoli

Who needs dryers?

Old mail box

Intrigued where the door leads to? Me too!

Little piazza in Radicondoli

Radicondoli town feast with a concert in the piazza

End your day at La Pergola. Order a pizza from their vast menu. Ask to sit on the terrace if it’s open. I recommend arriving early (an “early” supper in Italy is 7:30 p.m.) and watching the sky shift to orange and pink behind the hills. It’s one of those moments that makes you put your phone away, even if you're tempted (okay, maybe just one photo).

With Friends Liz and Mat at La Pergola. Thank goodness for doggy bags

Pam and Emi sunset at La Pergola

I bring all my visiting friends and family here, and it’s always a big favorite. So next time you're in Tuscany, make it a day excursion. You might even see me reading my book or strolling one of the little alleys.

Arrivederci until next Saturday, always observing, always sharing, always sipping, always a tale from an Italian coffee bar and beyond.