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Italy Self Catering holiday properties in and around Tuscany

Castellina In Chianti in Tuscany

Castellina In Chianti. Tuscany. Italy
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From £loading... for 7 nights
Vacation home in a former barn 3 km from Poggibonsi. In this very beautiful structure, the original structure has been preserved and it is located in a context typical of the Chianti countryside, surrounded by vineyards and olive groves and with a 360° view. It offers total privacy. A large fenced lawn surrounds this house full of character, tastefully furnished inside as well as outside. The atmosphere is that of the classic Tuscan country style, which has made this area famous worldwide. The bright interiors, the furniture of excellent workmanship, the beautiful lawn, children's playground, a lounge area and a terrace for outdoor dining, make it an ideal place for those who seek first of all total relaxation and tranquility. Then you can set out to discover the surrounding area, from the cities of art such as Siena (30 km), San Gimignano (15 km) and Florence (50 km) to the territories of Chianti Classico: known and appreciated worldwide for its beauty, art, culture, good food, wine and precious oils.

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About Castellina In Chianti. This former barn, 3 km from Poggibonsi, sits in classic Chianti countryside amid vineyards and olive groves with panoramic views. The original structure has been carefully preserved, offering total privacy within a large fenced garden. Tastefully furnished in traditional Tuscan style, the property features bright interiors with quality craftsmanship, a children's playground, a lounge area, and a terrace for al fresco dining. Ideal for complete relaxation, it also serves as a perfect base for exploring Siena (30 km), San Gimignano (15 km), Florence (50 km), and the renowned Chianti Classico region with its art, culture, food, wine, and olive oil.
Nearby attractions. Thermal bath: 40 km Airport (FLR): 55 km Nearest habitation: 300 m Fishing: 2 km Shopping: 4.5 km Restaurant: 2 km Nearest city: 10 km (Castellina in Chianti)
About Tuscany
I should have known the holiday was going to be eventful when I tried to unlock the wrong villa with the wrong key while a very patient German couple watched from their terrace. Three hours of driving from Pisa, winding through cypress-lined roads that looked stolen from a Renaissance painting, and there I was, jiggling a key at a door that very clearly had a different number on it. My partner, ever helpful, had wandered off to photograph a lizard. Typical.

The actual villa, when I finally found it, sat perched on a gentle slope just outside Castellina in Chianti, all honey-coloured stone and terracotta tiles. The key turned with satisfying weight, and we stepped into a kitchen that immediately made me want to cook everything. Terracotta floors, wooden beams thick as railway sleepers, and a window framing olive groves that rolled away like a green sea. I opened the fridge to find it empty except for a bottle of local olive oil left by the owners, golden and peppery, with a handwritten note suggesting we try it on everything. Challenge accepted, I thought.

By then it was late afternoon, and my stomach was making noises that echoed off those vaulted ceilings. We drove the ten minutes into Castellina proper, a medieval hill town that clings to its ridge like it is worried someone might steal it. The Coop supermarket on the edge of town became our first pilgrimage site. I have never been so excited by aubergines in my life. They were plump and glossy, piled beside tomatoes that actually smelled of something, and bunches of basil so fresh they were practically vibrating. I filled a basket with pecorino, cured meats I could not pronounce, and a bottle of Chianti Classico that cost less than a London sandwich. The woman at the till smiled at my enthusiasm in that way Italians have, part amusement, part pride.

That first evening, I attempted bruschetta. How hard could it be? The bread, bought from a bakery in town that morning, was dense and chewy. I charred it slightly on the ancient gas hob, rubbed it with garlic that made my eyes water, and piled on chopped tomatoes and basil. Simple. Perfect. I stood at the kitchen counter eating three pieces before my partner even sat down, olive oil running down my wrist, feeling genuinely pleased with myself. This was the life. This was why people came to Tuscany.

The morning market in Castellina's main square became our ritual. Every Wednesday, locals and a few knowing tourists gathered beneath the medieval walls. I learned to arrive early for the best porchetta from a van whose owner had been slicing it for forty years, the meat fragrant with fennel and slow-cooked until the fat melted into something almost sweet. We bought pecorino aged in walnut leaves, sheep's milk cheese that tasted of the hills themselves, and paper-wrapped packets of fresh pasta from a woman who made it in her kitchen nearby. I once tried to ask her about her technique in my phrasebook Italian, and she patted my arm and said something rapid and kind that I completely failed to understand.

My cooking ambitions grew with each passing day. One evening I attempted ribollita, the Tuscan bread soup, using a recipe I found in a battered cookbook in the villa's living room. I soaked cannellini beans overnight, chopped cavolo nero with more enthusiasm than skill, and layered in thick slices of day-old bread. It simmered for hours, filling the villa with smells that made us both ravenous. The result was somewhere between soup and stew, more rustic than refined, but eaten on the terrace as the sun dropped behind the hills, it tasted like the best thing I had ever made. We finished the bottle of Chianti, then opened another.

Not everything succeeded. My attempt at cantucci, the almond biscuits meant for dipping in vin santo, emerged from the oven as something closer to gravel. I ate them anyway, stubbornly, with my morning coffee, pretending they were meant to be that way. My partner, wisely, stuck to the bakery's version after that.

The villa's outdoor grill saw heavy use. Local sausages, thick with fennel, sizzled beside courgettes from the market, their skins blackening and splitting. I learned to judge the heat by holding my palm above the coals, a technique that cost me some arm hair but gained me confidence. We ate late, as the Italians do, sometimes not sitting down until nine, the sky darkening to a deep blue scattered with stars undimmed by city light.

On our final morning, I made one last trip to the bakery for fresh cornetti, those curved pastries that shatter into buttery flakes. I ate mine standing in the square, watching Castellina wake up around me, shopkeepers hosing down pavements, an old man walking his dog with the unhurried pace of someone with nowhere particular to be. I thought about all the meals we had cooked and eaten, the small failures and unexpected triumphs, the way food here seemed to matter in a way it rarely did at home. It was not just sustenance; it was conversation, with the land, with the season, with the people who grew and made what ended up on your plate.

I left with olive oil stains on my favourite shirt and a new appreciation for keeping things simple. And perhaps, if I am honest, with the vague notion that I might, someday, learn to make pasta properly. Though probably not the cantucci. Some defeats one must accept with grace.
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