I picked a tip of lavender, raised it to my face and inhaled deeply through my nose. On the horizon, the barely visible town of Montalcino squinted back at me from above a landscape that, softened by the haze of woodsmoke, had the unwrinkled flow of silk. The only sounds were birdsong and the air as it fizzed through the darkened silhouettes of nearby cypress trees. The quiet was almost unnerving.
I needn’t worry, I thought: this was Tuscany in early spring. But the truth is, I was worried about this trip: a long-weekend life coaching retreat with six strangers in a remote villa near Siena. A kind of social in-betweener, I’m not shy but I’m not an instinctive talker either. And I can often surprise myself: at times something close to extroversion, at others an encircling, irrational quietness. Which version of me would turn up, I wondered.
As the group gingerly assembled in a herb garden, some of us seated on candy-striped day beds, I read the room: creatives, probably, sensitive types, my kind. Slowly we began talking softly, each answering the same question: why are you here? “Since Covid, being fully freelance, at my age, I feel a bit… well, it’s harder to connect, isn’t it?” I said, tiptoeing around the point. “I suppose you could say… I’m lonely.”
Later that afternoon, as the light turned orange, small tufts of smoke appeared on the distant rippling hills and the spring air began to sharpen. I found Claudia Guinness, the retreat’s founder, in the villa’s kitchen, arranging the table for dinner. She thanked me for my candour in the group session. One of the reasons she’d set up the retreat was to build a community. “Loneliness, or a sense of dislocation, is now so common,” she said. “Reconnection is so energising.” I confided that I was sceptical about life coaching; that I thought the retreat might be too woo-woo and I’d struggle to hide my cynicism. She laughed: “That’s normal, it’s still a fairly new thing and even my family and friends aren’t quite clear what it is.”
I’d read that life coaching is like having an ally in the small war with your irrational, imposter-syndromed self – someone to help dismantle the scaffolding of self-doubt and design your dream life. “But isn’t that therapy?” I asked Guinness. “I like to think life coaching is more forward-looking, more solutions-based,” she replied. In her 20s she worked in film but felt rudderless, lost, a bit lacking. “But then a life coach changed my life,” she said, lighting amber-coloured candles as the last of the day’s light spilled through the window. “And so I gave myself a mission: to make people understand that life coaching really can work.”
Next door in the sitting room I made myself a gin and tonic, sat by the fire and slowly turned the pages of a photo album as Chet Baker played quietly. The Guinnesses are a family of overachievers, it turns out. Claudia’s sister, Amber, is a food writer and cook based in Florence; her mother, Camilla, is an in-demand interior designer who, with husband and self-taught landscape architect Jasper, acquired this house in the late ’80s. Villa Arniano is still the family home and not just a monument to magnificent taste, but also to hard graft: a photo dated 1989 shows it as an inglorious ruin that no sane person would bet on. No wonder Claudia is an optimist, I thought.
The next morning we lined up in the garden for yoga, dandelions and daisies slowly opening in the rising sun. My tendons said a firm and unforgiving no to anything close to an acceptable downward-facing dog. After breakfast we sat around a large shaded table for our first proper meeting, a “values session” where we mapped ourselves out. It was an odd feeling; I’d never put down on paper who I was before, much less discussed it in a group. But as we began to join the dots between who we were and who we might want to be, traits emerged and it became clear how they could be organised to create a more trim and tailored version of ourselves. The chat was just as nourishing: there’s a strongly adhesive quality to comparing life notes with intelligent, sensitive people, and trust formed surprisingly quickly as our inhibitions eroded and our conversation became loose and unguarded.
Later that afternoon, after a second session and hike to a nearby village that ended with a spritz, we sipped wine in the garden and someone suggested a game: “Act out your favourite pasta shape.” In the silence of Tuscany, there was a thunderous roar after the first successful guess (bucatini). I didn’t know I had a version of myself that could successfully charade rigatoni, but I liked it.
Our weekend passed like this: slow reflective meetings punctuated with delicious food, a group activity or nothing at all. On Saturday we rose for a silent sunrise walk and were led through a darkened, gently swaying olive grove and past a makeshift road sign that seemed to whisper its single Italian word: adagio (slow). At breakfast someone recited an impromptu version of a Kobayashi Issa haiku: “The morning dew / The morning dew / And yet, and yet.”
That afternoon in the kitchen, a wood fire popped and cracked as we gathered around the table to make hand-rolled pici (a kind of ugly spaghetti) while sipping chilled Vermentino from old Parisian glasses. Doors open to crisp air, the whole space glowed in soft late-afternoon sunlight as our teacher, Grazia, an Italian woman in her late 50s with a broad forgiving smile, gently steered us without a word of English. In the evening more wine flowed as we ate our al dente efforts by candlelight, and the conversation sparkled with smart questions and thoughtful – and often very funny – answers.
On our last morning, something was off. The light I’d got used to seeing from my four-poster was absent; the quiet was somehow different. Outside, the land had disappeared in mist: all I could see were skinny cypress trees, black and tightly furled like bats hanging in a cave. I stupidly checked my phone: elsewhere in the world it was Trump’s “liberation day”, the stock markets had slumped, fortunes had been lost. I resolved to make the most of the day and its “future self” theme, where the concept of “glimmers” emerged. The opposite of triggers, they are the small things that bring us joy.
After a circular hike in the Tuscan hills, we dressed for our closing evening, the villa buzzing with excitement. A fire was lit outside as we clinked glasses of sparkling wine in honour of our brief but profoundly meaningful union that had delivered on its promise: the chance to rest and reconnect. Not a total reinvention of the self, more a soft reboot. Charged with optimism, we read our anonymous reflections out loud from scraps of paper. Mine was last: “How rare and beautiful it is that a group of strangers can come together and find the space to be themselves. Who could ask for more?”
The next four-night Alba retreat runs from 2-6 October, with prices from £1,200 per person, full board; claudiaguinnesscoaching.com