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Experience the beauty of Tuscany, the birthplace of the Renaissance, in ultimate comfort and style. Find your perfect holiday property and speak to our team for bespoke support.
Tuscany is truly one of Italy’s most captivating regions. Browse our beautiful collection of luxury holiday villas in Tuscany, Italy, from countryside estates in the Chianti wine region to elegant homes near Florence, Siena, and Lucca.
Each of our luxury holiday villas have been selected for their convenient setting, authentic character, and unparalleled comfort, offering an authentic yet refined way to experience this timeless destination. Whether set amongst rolling hills, close to historic towns, or a stone’s throw from the Tuscan coast, experience effortless Italian living in our hand-selected collection of holiday villas.
Art, Architecture & History
Tuscany is a region defined by its multi-dimensional artistic and cultural heritage, with cities such as Florence, Siena, and Lucca showcasing some of the greatest works of art and architecture in the world. With its Renaissance masterpieces, frescoed churches, grand piazzas, and medieval streets, Tuscany represents Italy’s rich cultural history at its finest.
Countryside Vineyards & Hilltop Towns
The Tuscan landscape is not hard to recognise. Rolling hills, vineyards, olive groves, and cypress-lined roads mark the landscape, stretching across the countryside canvas. Must-visit hilltop towns include San Gimignano, Montepulciano, and Cortona, as well as the wider Chianti region, renowned for its first-class wine estates and rustic, rural atmosphere
Val d'Orcia & Coastal Landmarks
As a region, Tuscany is extremely diverse. It extends from the UNESCO-listed Val d’Orcia, known for its sculpted landscapes and picturesque villages, to the beautiful, 300km-long Tuscan coast. Whether you wish to explore inland or by the shoreline, Tuscany effortlessly masters both in equal measure.
Our Tuscany portfolio includes restored stone farmhouses with private pools among the cypress-lined hills of the Val d’Orcia, elegant private villas on working wine estates in the Chianti Classico such as Villa Romea and Villa Cappella Del Lupo, and discreet country residences within reach of the medieval hill towns of Siena, Montalcino, and Montepulciano – each personally vetted and supported by our full concierge service.
Tuscany demands its own transport – its network of white gravel roads connecting hilltop villages, vineyard estates, and weekly markets are best explored with the freedom to stop at will. A private driver is invaluable for wine estate visits, evening dining, and longer excursions across the region. We work with a small number of trusted, discreet drivers and can arrange dedicated transport for the duration of your stay.
Florence Peretola and Pisa airports are the most convenient gateways, both served by direct flights from major European cities. Rome Fiumicino is a useful alternative for properties in the southern Val d’Orcia, under two hours by road. A pre-arranged private transfer is the most seamless arrival – let us organise this ahead of your trip.
Tuscany is renowned for cucina povera, a cuisine characterised by rustic, simple ingredients. Think unsalted bread, beans, olive oil, and wild game in the form of soups, stews, and small plates. Tuscany is also famous for its Pecorino cheese, fennel salami, and Cantuccini biscuits. There is also a strong Chianti cuisine based around high-quality olive oil, wood-fired bread, and local meats to reflect the wider wine region.
The Val d’Orcia – a UNESCO landscape of rolling hills, cypress avenues and medieval villages – is Tuscany at its most cinematic, with Pienza, Montalcino and Bagno Vignoni the essential stops. Between Florence and Siena, the Chianti Classico is Italy’s most rewarding wine country, its hilltop villages surrounded by world-class Sangiovese estates. To the south, the wilder Maremma coast offers a different Tuscany entirely – pine forests, Etruscan ruins and unspoiled beaches.
Siena’s Piazza del Campo – one of the greatest medieval public spaces in Europe – and its extraordinary striped cathedral are essential and best appreciated on a quiet weekday morning. The abbeys of Sant’Antimo near Montalcino and Monte Oliveto Maggiore, set in isolated wooded valleys, are among the most atmospheric religious buildings in Italy. The thermal baths at Bagno Vignoni and Saturnia are worth building into any stay in the south of the region.
Florence is within reach of most Tuscan properties and rewards a dedicated day in the Uffizi and the Oltrarno. The hilltop towns of Volterra and San Gimignano are among the most dramatically preserved medieval centres in Italy and easily combined for a full day. For wine, the Brunello estates around Montalcino and the Vino Nobile producers of Montepulciano are the most rewarding visits in the region.
Tuscany is an extremely versatile luxury travel destination, suitable for quaint countryside retreats, educational city excursions, romantic honeymoons, and coastal retreats. This region also offers picturesque settings for large groups and events. See one our beautiful properties Villa II Santo.
It is possible to explore a singular region of Tuscany within 1-2 days, such as Florence or the Chianti wine region. However, we strongly recommend a 7-10 day stay to experience the northern and southern highlights of Tuscany, combining bespoke experiences with a chance to immerse yourself in the region’s key towns, cities, and landscapes.
The agriturismi of Val d’Orcia and Chianti offer the most rewarding Tuscan cooking – pici with wild boar ragù, pecorino di Pienza, exceptional olive oil and Brunello. For considered dining, Osteria Francescana alumni have established some of Tuscany’s finest tables, with Il Pellegrino in Castelnuovo dell’Abate and Trattoria Buca di Sant’Antonio in Lucca among the most celebrated. For a special evening, La Bandita Townhouse in Pienza pairs confident modern Tuscan cooking with one of the Val d’Orcia’s most beautiful settings.
Whether you’re seeking the high-octane party scenes at the best beach clubs in Mykonos and the hottest clubs in Ibiza, the more boho chic vibe of Comporta or elegant watering holes in Mallorca, Côte d’Azur, and the Amalfi Coast, we’ve got luxury villas close to the very best beach clubs in Europe.
