Villa Visits
I’m just back from a trip to Tuscany this September 2025, a long driving loop visiting owners, seeing houses, and exploring. After over 40 years I’m still finding new spots I hadn’t seen before, Tuscany really is an endless supply of delights.
Valdera and the view
I started with a visit to Valdera and carried out my time-honoured ritual of trying to take a good photo of the amazing view, and once again being disappointed by the results. Have a look at this, and just imagine that it’s much better than this!
Then Marco pulled up in his little Polaris so, with Cinzia, we all headed up to the bar for a coffee.
Ruins of a monastery
On Monday morning, heading to Pisa for Laura’s arrival by plane, I used some spare time to walk into the Pisan hills to have a look at the aqueduct that the Medici built to supply Pisa with water. It’s an impressive bit of engineering - with an arched aqueduct still standing, and a large an impressive pumping room hidden in the forest.
As an added treat I spotted signs to a monastery, so headed uphill on a tiny stone-paved hairpin mule-track until finally I emerged onto a clearing to find a roofless stone church.
A clattering half-run back down the hill got me to Pisa on time to pick up Laura and we headed off to Villa di Mezzo.
What a lunch! Sheba prepared dishes of figs and burrata, ham and melon, wild mushroom salad and so much more. It was a feast - she and Giuseppe are always wonderful hosts.
I had a moment to take some drone footage - it's always helpful to show quite where the houses are:
Time to go and see Piaggia, Leccio and Guardiolo, three beautiful houses on a wine estate between Pisa and Florence. Laura hadn’t seen these, and we had had a complaint about Leccio, and I couldn’t square it with my memory of the place. I was reassured: Leccio is still the beautiful place I remembered.
Laura and I would be staying in Pinolo as the base for our villa visits so we headed back there, after a brief stop at the Consorzio Agrario at the top of the hill. The many Agresto aficionados will be pleased to hear that Elvira, now in her nineties, is stilling doing well, and as formidable as ever.
Tuesday in the Val d'Arno and Chianti
Tuesday held visits to Villa Ema, Borgo Rinnovato, Podere Gregorio, in the morning.
I managed to get the drone up in the air for some shots of Borgo Rinnovato too - it's in an amazing spot on the edge of the Tuscan apennines.
Lunch in Radda in Chianti
If you’re in Radda make sure you go for a meal in the covered alleyway, at Casa Porciatti.
Laura and I stopped here for a bite to eat before going to see Anna and Luciano at Docciole, and it’s a delight. Docciole, by the way, is looking lovely - we’ve had a lot of happy clients there this year. We wanted to check a couple of things, and you’ll be happy to know that the pool decking is being completely replaced over the winter.
And then on to Borgo Castello, Podere Castello, Contenta and Starna. Maria Cristina opened up the church for us, and we stood in the nave as she clicked on the lights in sequence - it’s always an amazing view.
Wednesday in the Val d'Elsa
On Wednesday we started with a visit to Montestigliano. I’ve been visiting Montestigliano since the early 1980s and it remains one of my favourite places. The hills to the west are wooded and full of secrets (my favourite is the “Castiglion she Dio sol sa” (The Castle that God only knows). The views to the east are of the agricultural plains that fed Siena, the well-tended fields of Ambrogio Lorenzetti’s “Buon Governo”.
Montestigliano sits between the wild and the civilised, balanced like Douglas Adam’s Restaurant at the End of the Universe. We wandered up to Pipistrelli, generally poked our nose in a few places, said hello to Francesco and met Maddalena.
Lunch today was at the Bar dell’Orso near Monterriggioni, a deservedly famous eatery still favoured by most of the local workers (always a good sign).
Then Dimora, where Violante and Vieri have been improving, improving, improving. Dimora has always been a popular house but clients had been suggesting some improvements for a while, like a stepping stone path to the pool across the lawn, better lighting, moving the barbecue and more. It’s all being delivered and I’ll be going back in spring to see it all, but they are hard at work.
Off towards San Gimignano, and I pointed out Casa Andrea to Laura as we drove past - we didn’t want to disturb our guests during their stay. Our last visit for Wednesday was Torrevista, a house on a ridge near San Gimignano, with million dollar views of the famous towers, but an affordable price tag.
Owned by a charming Swiss composer, I finally met him and his wife - all my previous visits had been with the caretaker. The house has improved over the years, most notably with the addition of decent insulation in the roof, lengthening the season for rentals. But it retains a quality that I treasure in some houses, a Tuscan farmhouse inhabited with a light touch, where, while perhaps the old threshing ground has been replaced by a pool, the house still breathes and lives with the old rhythms. As a bonus, Christoph does make a particularly fine wine - a Chianti suffused with the strength and vigour of the SuperTuscans.
Wednesday evening saw us in Colle val d’Elsa with Stefano and Katia from Agriturismo Elvira, at a great little pizzeria called “Bocca Garage”, carved out of a series of interconnected rooms. A post meal stroll into Colle Alta, the medieval part of the town, took us across the bridge that leads into the arched gateway of the impressive villa facade designed by Baccio d’Agnolo, an unusual and impressive way to enter a town.
Thursday for Umbria and the Val d'Orcia
Thursday was a long day, starting with a drive down to Paciano, the little village in Umbria where Ed Sheeran bought a place a few years ago. We had a look at the apartments in Podere Vocabolo, a farmhouse just a short walk from the village. They’re rustic, but the charm of being so close to the village offsets their simplicity, and the view of Lake Trasimeno also helps.
Claudio, also the owner of a boutique hotel in the village, showed us some new places he’s getting ready, 4 or 5 apartments right on the edge of the village - more on these as they are readied.
Next on the list was Aceronina, an amazing place on a farming estate. It’s like entering a Tardis, everytime I visit I’m surprised by the size and quality of the rooms.
On our way to San Casciano del Bagni I pointed out the entrance to Villa Bosco, close enough to walk into town, to Laura. Sadly we couldn’t stop (sorry Patrizia, passo la prossima Volta!) but went on for a quick lunch in San Casciano but, more importantly, I finally got to walk down to the outdoor hot baths where some amazing bronze statues were recently discovered. They’ll be shown in a purpose built museum soon - they’re currently touring Italy, but it was a pleasure to see the stone baths, still in use today, 2000 years later.
Looking west from San Casciano you’ll see a high hill topped with a formidable fortress - this is Radicofani, a formidable stronghold from which a famous brigand “Ghino di Tacco” was said to plunge down to raid the pilgrims making their way to Rome along the Via Francigena.
We were stopping short of the fortress itself, going to visit Nicoletta at Villa Bianca, a large villa for 24 that we’ve recently listed.
Owned by Nicoletta’s family for generations, it has history in its walls, but also plenty of thoughtful additions. Any visit where a client expresses a thoughtful wish seems to result in Nicoletta dashing off and making it come true. So the house has an EV charger, a pool table, innumerable board games, a gym, yoga mats, table football (always popular), and much more.
Finally we could start wending our way north, heading up towards the Val d’Orcia to visit Casa del Pastore. We’ve been renting it for a long time but it was recently bought by new owners and they’d been making some changes. We’d also had reports that the gravel road was worsening and some guests were unhappy with the changes, so we had to go and check.
Casa del Pastore, for those who don’t know it, is in a spectacular position on a ridge, with long-reaching views towards the spent volcano that is Mont’Amiata. The old mountain, around 1300 metres high, is a wonderful place to visit during hot summers, with a few restaurants right on the summit, next to a giant iron cross. A village on the slopes, Abbadia San Salvatore, is home to one of the most beautiful crypts I have seen, built in the 9th century by the Longobards when they controlled this area of Tuscany. The crypt was used for a magical scene in Tarkovsky’s film Nostalgia, when a statue of a pregnant madonna had her belly unlaced and sparrows burst forth, racing through the vaults of the crypt. Magical, poetic and quite Russian.
Meanwhile, we were wandering through Casa del Pastore and meeting Dila, a lovely Rhodesian ridgeback. Matthias and Ariane, the new owners, have opened up a new corridor between the kitchen and what used to be a living room, turning it into a living/dining room. They’ve changed the old fireplace into something that works, and added new sofas. I thought it all worked rather well, and their enthusiasm and love for the place is infectious.
The road, on the other hand, always a long gravel track, has suffered a little over the summer, and is a bit bumpy in places. I’m no great judge, having driven on these roads all my life, but it will need a little TLC.
Friday
It’s Friday, and I’m driving Laura to the airport - it’s been a good trip and it’s always good to visit places together. After I drop her off I head to Treggiaia, a little cottage between Florence and Arezzo. We might be letting out the main house, next-door, and the owners also have a beautiful flat in Florence and a little chalet in Cortina d’Ampezzo, so you’ll see these going up soon!
Saturday brings a ruined castle
On Saturday I headed back into Chianti to see a beauitful house that I think we perhaps listed in the 90s - I have to check our old brochures. While chatting with the owner I saw some ruins on a nearby hill: aha, yes, Michael said, the ruins of Castello del Cerretaccio, one of Siena’s many strongholds against Florentines’ incursions into their territory.
So I headed off to explore and found the ruins deep in holm-oak forests. The castle must once have had a tall watchtower, toppled when its defences finally failed. Now it lies on its side by the old gatehouse, its massive structure still intact and forming a tunnel that, with caution, I explored.
Standing there in the green-filtered light of the holm-oak forest, looking at these massive stones that once guarded Siena's northern frontier, I was reminded why I never tire of these hills.
Even after forty years, there's always something new to discover - a hidden Medici aqueduct, a roofless monastery, a fallen watchtower - each one adding another story to the endless narrative of Tuscany.
Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
1st Jan 2026 17th Oct 2025