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Boutique holidays in Tuscany
Medieval marvels, vineyard vistas and flavours worth lingering over
From its golden hilltops to its Renaissance cities, Tuscany is Italy at its most timeless. A region of vineyard-striped valleys, terracotta towns and extraordinary food culture, it’s where art, history and la dolce vita quietly intertwine. From the cultural icons of Florence and Siena to the peaceful rhythms of the Val d’Orcia, this is a destination that rewards both curiosity and stillness.
Charming medieval villages such as San Gimignano and Montepulciano invite you to wander their cobbled lanes, glass of Brunello in hand, while lesser-known towns like Pienza and Arezzo offer intimate glimpses into everyday Tuscan life. It’s a region made for lingering over long lunches — truffle pasta in tiny trattorias, fresh pici with wild boar ragu, wedges of pecorino from the shepherd’s market, and wines poured by the people who made them.
Whether you dream of hands-on experiences or long afternoons beneath the cypress trees, Tuscany lends itself effortlessly to a tailor-made holiday with the Discerning Collection — rich in customs, traditions, and authentic moments you won’t find in a guidebook. Do as much or as little as you please — either way, it will linger.
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Our accommodation in Tuscany
Tailor-Made Stays, Tuscan Style
Rather than being rooted in one place, our Tuscan holidays are designed as seamlessly tailored journeys — carefully woven from a selection of distinctive boutique properties, each handpicked for its location, character, and the richness of experience it offers in its village, town or countryside setting. From medieval castles rising above silver-green olive groves to former mills tucked between sun-drenched vineyards, these are stays with real soul — where the rhythm, flavours and charm of Tuscany infuse every moment.
You might wake to the scent of warm focaccia in a lovingly restored 15th-century mill in Chianti, sip wine with the family who grew the grapes at an agriturismo in the Val d’Orcia, or trace history along the ramparts of a hilltop hamlet above the Chiana Valley. These handpicked hideaways are as integral to the journey as the landscapes themselves — chosen not just for beauty, but for their authenticity, their intimacy, and the genuine warmth of their welcome.
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