Holiday homes in Tuscany: the region of Chianti has protected architecture, legendary vineyards and breathtaking views

Holiday homes with Tuscan charm pepper the lush landscape of this ancient and beautiful Italian wine region, a perennial British favourite.
1/10
Cathy Hawker18 May 2019

One of Europe’s best known, most beautiful and oldest wine regions, designated by Grand Duke Cosimo III de Medici in 1716, Chianti covers the heart of Tuscany, stretching south from Florence to Siena and centring on the towns of Radda, Greve and Gaiole in Chianti.

This wild Italian landscape is marked by neat lines of red sangiovese grapes, olive groves and hilltop towns.

Quietly sleepy in winter, summer brings tourists in their millions. Florence and its Renaissance art and architecture is the main draw but the chance to drive Chianti’s winding country roads, stopping to marvel at the view or for wine and olive oil tastings over lunch at a family-run trattoria, is also a big part of the appeal.

This was the region that first sparked our dreams of a Tuscan holiday home. In the Seventies and Eighties, Britons bought ramshackle farmhouses to renovate.

Celebrities including Sting and Trudie Styler followed and then politicians got in on the act: Tony Blair and David Cameron both enjoyed family holidays there while serving as PM.

The region became known as Chianti-shire for good reason.

“Chianti’s popularity is largely because of its well-preserved, beautiful landscape,” says Jelena Cvjetkonic of Savills.

“Planning is carefully controlled and all homes must be restored along strict guidelines, keeping original details on the exteriors. What buyers increasingly want, however, is a contemporary twist on interiors.”

Chianti is a truly international market for second-home buyers. Property prices have been stable for the past year, 20 to 30 per cent below pre-2008 highs but with some notable and substantial sales last year.

Currently for sale, three miles from Radda, Savills has a well-restored stone house with four bedrooms and gardens with pool for £561,000 and a two-bedroom flat of 1,100sq ft in the small village of San Sano with private garden and communal pool for £254,000.

A hilltop farmhouse close to Radda in 10 acres for £734,000 needs total refurbishment but could make a splendid five-bedroom home. Contact Savills: savills.com (020 7016 3740)

A holiday home in Chianti

Londoner Margherita Piliero was brought up in Nottingham by Italian parents. As a child she holidayed in Basilicata, southern Italy, every year.

It wasn’t until she holidayed there with her husband, Iain, who is British, that she began to think about buying her own Italian home.

Londoner Margherita Piliero renovated Le Pratola, Galole in Chianti, for her family holiday home and as a rental villa
Adrian Lourie

“I fell in love with Tuscany, which has the weather of the south but also great beauty, refinement, wonderful food and culture,” she says.

In 2006 she viewed Le Pratola. “The house was an empty shell with small windows and only a ladder to the top floor. It was the location in beautiful Chianti that sold it. The views over the countryside, vineyards and olive groves are outstanding.”

Margherita recruited Italian-based project manager Joe Thompson who along with a specialist surveyor and creative, bilingual builder, assembled a “dream team” of craftsmen.

Margherita invested heavily, using 200-year-old floor tiles, adding a travertine staircase and underfloor heating, air conditioning and efficient eco-systems among modern-day comforts.

Furniture came from Florentine auction houses with contemporary additions from Kartell and Roche Bobois.

Renting a house in Tuscany

Le Pratola is now a handsome five-bedroom home at the end of a long drive lined with cypress trees.

A central courtyard leads into a modern kitchen, dining room and two sitting rooms, a gym and games room. The five-acre gardens contain a large infinity pool. This is a generous-size holiday home, perfect for a large group or family yet with many quiet corners.

Margherita, a mother of three, has now traded her City job for a career in property renovation. Le Pratola has been available to rent for several years but last year she launched a rental company, also called Le Pratola, with three other historic properties, in Rome, Venice and Florence.

All are privately owned and professionally managed with five or more bedrooms and a high level of finish and services.

“These are legacy properties where owners have invested heavily and guests feel a true immersion in the culture and history of Italian life,” Margherita says.

“We offer hotel services in the privacy of your own space. Guests can have as much attention, including cooks, housekeepers or drivers, as they want.”

She will arrange cookery lessons or celebratory dinners, book restaurants and advise on the best wineries or ceramic studios to visit. She plans to add more rental properties, perhaps on Lake Como and Milan.

“Le Pratola rents for around 20 weeks a year and my family spends up to seven weeks there,” she says.

Le Pratola rents from £7,380 a week for 10 adults.

What to do and where to stay in Chianti

1. Wine Tasting: Tenuta Casanova

Silvano Cis and his wife Rita own Tenuta Casanova, an organic winery with 77 acres near Castellina in Chianti, ranked as one of Europe’s top 10 cellars by TripAdvisor.

Silvano also produces olive oil, honey and balsamic vinegar, harvests lavender and rosemary for body lotions and hunts out truffles with his two dogs.

He guides visitors around the estate before Rita serves lunch. Cookery courses and wine tastings are also on offer.

2. Ceramics: Studio Radianza

Dutch artist Lies Robbertsen paints and creates ceramics inspired by the Tuscan countryside, selling her beautiful work in the tiny village of Lecchi in Chianti, population 110.

Lies, who trained at the Royal Academy in The Hague, says: “I never want to leave this friendly village.”

3. Stay in Lecchi in Chianti

This beautiful village has one restaurant, two churches and next door to Studio Radianza, a small food and wine shop, the hub of the place, run by Paolo.

If your budget doesn’t stretch to Le Pratola a short drive away, he has two comfortable, newly renovated two-bedroom flats to rent above his shop, from £103 a night.

For details, email Paolo at rinaldivini@si.technet.it

4. The perfect wine shop and bar in Gaiole in Chianti

Ricardo Azzato sells wine, local hams, cheeses, oil and balsamic vinegar, pasta and sauces.

Sit outside in the small piazza to try the wines, sourced from across Italy but mostly Chianti Classico.

5. Dinner at Il Celliere, Castagnoli

A hamlet of Gaiole, Castagnoli is built on a hill around medieval Rocca di Castagnoli fortress, which has 10 guest rooms, a wine shop and Il Celliere restaurant.

The menu is based around Tuscan dishes: pappardelle ragu, pecorino soufflés and bruschetta with truffles.