Brunello and Best Friends: The Ultimate Tuscan Getaway

What are your thoughts on truffle ketchup?

Silencio. Echoing silencio. High in the Tuscan hills our guide for the morning, Valentino, is struck dumb by this obtuse, but unabashed, line of questioning. Truffle fusions - our go to is oil-drenched French fries - and truffle condiments in particular are a no-no for any Tuscan worth their salt.

We continue deeper into the shrouded woodland, three sniffer dogs in tow. Conversation shifts as our first truffle is unearthed. The dogs begin to dig furiously and a small black truffle surfaces. A few feet on, the scene repeats. Because truffles grow inside tree roots, they can't be cultivated and so can still only be sourced in the wild. These pungent underground fungi, garner pretty hefty returns; prices are now as high £4,000 per kilo.

We have been briefed that it is unlikely we will find anything while we are out here; truffles are deceptively good at hide and seek. And yet, already we have found two. The cynic in me considers that it is a fix, but I am overruled and we walk for a while longer. Nothing. Then Mara (a springer and the most rambunctious of the pack) begins to run and latches on to a patch of ground. A deep, pungent scent emerges from the soil - along with lashings of dirt and muck hurdled in every which direction. Mara is a determined, but not particularly tidy, digger. And then we spot it. A white truffle; 200g at that. We ask: can we keep it? Silencio.

We're in Montalcino, 12 kilometres from the Rosewood Castiglion del Bosco, an 800-year old Tuscan estate which we are calling "home" (rather thrillingly) for the next three days. Our visit is the result of one very organised friend - and Rosewood's Ultimate Girlfriends Getaway package. Throw out the words "private villa" and "spa treatments" into the group WhatsApp and the response rate is (as you might guess) supremely faster than when frantically fundraising for a parkrun or selling tickets to your fringe theatre debut. In any event, after excuses are made and apologies are given, our final group comprises of creative director Fiona Leahy, chef Clodagh McKenna and Jessie Garland-Blake of @ihavethisthingfor. A mishmashed but motley crew, our sights are set on convivial wine drinking (given that we are neighbouring a private 5,000-acre wine estate) with the occasional outdoor pursuit thrown in for good measure.

Back at Castiglion Del Bosco, we saunter along to the hotels' more casual dining space, Osteria La Canonica, and ready ourselves for lunch - a chorus of pizzas, from the traditional Toscana to the lauded truffle-topped pizza pie, are served on long wooden boards. Heckled towards the centre of the table, the truffle pizza is promptly demolished. Between chomps we self-congratulate for bearing witness to the bounty we are now guzzling as though we are fishermen who have waited for our catch for hours on end. Plates are cleared, top buttons undone and we roll home in sync with the undulating Tuscan terra.

Our villa at the Rosewood Castiglion del Bosco has a toned-down rustic aesthetic, decorated in shades of ochre and flaxen, with shuttered windows and furnishings worthy of a Nancy Meyers movie. Canopied beds, generous bathtubs and vast wardrobes are given a coveted double thumbs up by each of their occupants. Pillows are topped with presents; night one delivers a Skinesis Sarah Chapman facemask to appease our carb come down and impending blotchy skin.

In Italy, and Tuscany in particular, days seem to centre on food. Italians break for an hour after a long lunch and then start the ritual all over again. A poolside photo shoot involving tasteful lavender sprigs and bushels of velvet is interrupted by the arrival our private chef, Ludovico, under whose instruction we are going to cook dinner. Something light? Sacrilege. To start: pasta. We make a small well with our pre-portioned flour and semolina mix and then whisk the eggs, slowly adding it to the central mixture. Positioned between a food journalist, the daughter of hoteliers and the girlfriend of a chef, my below-average cooking skills feel increasingly exposed. Taking solace in the well of flour's concealing nature, my not-so-bad but also not-all-that-good efforts are shrouded from judgment. The Tuscan cucina (cuisine) is more complicated than I had anticipated. Three minutes in and it becomes clear I need a little assistance in perfecting (read: salvaging) my dough. Cooking with friends seems a decidedly better idea than cooking for friends and is certainly an activity best suited to those less kitchen confident. Time passes by, the slicing of the celery is criticised and a hearty red sauce is left to simmer as we make a start on the tiramisu. Then, while our ever-patient chef makes the final touches (or quite possibly places our attempts in the dustbin and starts again from scratch), we saunter upstairs to change for dinner.

On our return - long dresses skirting the floor to hide our hotel slippers - the dining-room table has been transformed. Decorated with dahlias and in-season vegetation - in the corner our private butler is on standby with an Italian aperitivo. Glasses clink and we take our seats, following a table restyle by Fiona. An amuse bouche; a first course; then a second appears. Candles melt right down to their base. Over mottled light we unpack our views on spiritualism, the plausibility of Facetuning a napkin and a few mandatory Brexit concerns are uttered before chat quickly reverts to truffles and whether there is any nutritional benefit in their consumption (there isn't). On that dream-inducing note we go to bed.

The first to rise, I scurry downstairs to a sumptuous spread already laid out in the kitchen. Laurenco is waiting to cook us eggs and bacon but the apple pie, zucchini and bacon quiche, not to mention Tuscan bread, homemade pastries and Tuscan cold cuts from the farm seem ample fodder. I take a liking to a generous slice of pie and plot myself at the kitchen counter, accompanied by a steaming coffee and my laptop. Morning light seeps on to the terracotta-tiled floor. Someone appears from behind the fridge door. "Buongiorno", utters a voice that sounds like Jessie's before scurrying off upstairs again to get ready for our afternoon activity, pain au chocolat in hand.

Bundling into the car, in our "rural chic" cashmere and corduroy combinations (we collectively packed a lot of olive, corn-gold and russet-hued polo necks) we head out for an afternoon of convivial (and civilised) drinking at Castiglion del Bosco vineyard and winery. Seated overlooking rows upon rows of oak wood wine barrels, our glasses are topped up 10 times over. Here, at the fifth-largest producer of Brunello Di Montalcino, we sample a broad range of wines from the Prima Pietra 2014 and the 2015 to the Millecento Brunello Di Montalcino Riserva 2011 (basically the best bottles you'll find in the area), each paired with olive oil and cheeses and honey dolloped generously on top. We all decide we like the cheapest honey and the most expensive bottle of red, of course.

With a slight sway to our step, we are shown downstairs to the wine cellar, a crescent-shaped room caddying the personalised wine collections of the vineyard's most-prized members. Along the back central tier of the wine cavern we spot the Ferragamos personal collection. Chiara and Massimo Ferragamo - the youngest son of Salvatore Ferragamo (yes, that Salvatore) - who co-own the Castiglion del Bosco make their presence lightly felt. And yet their taste in wine is first class and flamboyant. The cavern is a Mayfair private-members club transplant in the making. As our first thoughts of home seep in, the last of the Brunello spills into our large size bowl glasses (which emphasize the firm tannins and cherry bouquet we've been told).

We've learnt a lot this trip, and yet as we stumble through Aeroporto di Firenze-Peretola's Duty Free we (or some of us, at least) revert to our hedonistic, habitual ways. "What's that you have there Fiona?" Coyly, she turns and bares her scarlet letter - a packet of Savini Tartufi truffle-flavoured crisps clasped in her hands. Silencio.

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