The Tuscan sun finally found me on Monday, as I headed to the sea. Following an itinerary suggested by my friend for each day of my long weekend in Tuscany, I drove the winding roads to see the charming, historic towns scattered around the hillsides. This post is a continuation as I drove to each village and walked its ancient narrow streets in 2007.
On my friend’s recommendation, I turned down a narrow dirt road, drove 3km, then hiked 1.5km through forest to be rewarded with a peaceful, pristine beach, Cala Violina. I would surely have never found this on my own! Bird footprints were the only other ones there that morning. I took off my sandals and strolled along the water’s edge.
Cala Violina
The high medieval city of Castiglione Della Pescaia was one of my favorites. Balanced on cliffs over the Mediterranean, it was one of the few places where there were no souvenir shops and cafes lining the streets—they were in the port below. It was a quiet town, residents hanging out their laundry, watering flowers. I felt as if I was intruding on the lives of those good people whose families must have lived on this stony perch for ages. The Castiglione church bells tolled noon, a sound that seemed to follow me from town to town.
Castiglione Della Pescaia
One more stop at the small village of Roccaderighi and a drive through the valley of Chianti vineyards brought me back to the hotel.
Roccaderighi
That evening, after a grueling massage, I walked the historic streets of Massa Marattima in the waning light of sunset.
Massa Marattima
Nadine had been busy days with the hotel, and had seen all these places already, but we were able to visit a bit in the evenings. I told her this was probably the most romantic place I’d ever visited, and I’ll recommend it to friends. “Yes, it’s romantic,” she agreed, “but it takes a while to see that it’s not the man, it’s Italy you are falling in love with!”
We mused about the possibility of meeting in Florence (which we did the following year) or Prague. “You are like me—you have no sense of country,” she smiled when I said we will meet again somewhere.
Early Tuesday morning, I made a last drive around the resort ridden roads of Porto Santo Stefano and Porto Ercole on the way to the airport.
Porto Santo Stefano
Porto Ercole
The church bells at my local square in Prague, Jiriho z Podebrad, greeted me as I climbed the stairs from the metro at 6pm.
In Prague, I taught English at a language school. One activity I enjoyed doing with my classes is having students, in pairs, do a drawing exercise. One student describes the image to the other student (in English, of course), and the second student draws it. I used these two pictures from this Tuscany trip for many years.
Tuscany: Day1, Day1 part 2, Day2, Day2 Siena, Day 3
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Ruth Rosenfeld 
Beautiful images Ruth. It looks so serene in these small villages. Maggie
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Thanks so much, Maggie. It was peaceful and calm in those non-tourist stops.
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Always nice to find still some place that are not “infected” with tourism. Therefore you need some good tips from people who know the region. Thanks for the lovely images and the stories of your Tuscany trips.
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It always helps to have suggestions from locals. You’re most welcome, Rudi!
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Che meraviglia!
Le tue foto sono semplicemente stupende💙
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Grazie mille! I loved visiting your beautiful country.
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So glad to hear you loved it!!! 💞
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The casual “ordinariness” of the towns is what makes them especially charming.
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It’s a treat to see a town, that’s not a tourism site, where people are just going about their everyday lives.
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Such a charming place!
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Yes, it is! Thanks for reading.
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Fine essay. I really like this description: “It was a quiet town, residents hanging out their laundry, watering flowers. I felt as if I was intruding on the lives of those good people whose families must have lived on this stony perch for ages.”
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Thank you, Neil, for reading and your kind message.
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I’ve loved seeing this corner of Italy through your eyes and lens 😀 Castiglione does look especially beautiful but all the places you’ve shared are lovely!
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Glad you enjoyed this series! Each town has it’s own character and charm.
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Beautiful images. It’s so nice having a local or near-local friend who can give you all the hidden spots that tourists don’t know about.
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Thanks. That makes all the difference!
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Oh your posts are making me dream of a trip to Italy. It’s just so beautiful
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You should go! It’s not so far for you.
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What a beautiful beach. And how nice to have it all to yourself. Castiglione Della Pescaia looks like a charming city to wander around. No wonder it was one of your favourites. I’ll have to add this to the list for the next time we’re in Italy.
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I hope this series inspires you to explore this area’s little treasures.
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I’ve enjoyed your Tuscany series. What a rich three days you had. There’s something so magical about Tuscany, as if it’s been planted there by the gods or something.
Alison
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Thanks for coming along, Alison. I always appreciate your comments.
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Gorgeous! I feel you on the front about “having no sense of a country.” One would call that being a “global citizen!” Looks like you really fell in love with Tuscany, and I’m sure you’ll continue to return to visit more of its beauty some day!
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Perhaps not, it was so easy when I lived in Europe. But it will always have a place in my heart.
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The photo looking down to the sea and shoreline as it curves away is beautiful. But my favorite is the cobbled street with the arch, tables, and hat vendor. So much character in one small space!
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Thank you, Dave! So many lovely spaces like that one in these little villages.
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🧡🧡
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