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An insider guide to our regions

Renting a villa in Tuscany

The historical estates listed below have been carefully selected by Trust&Travel over the past years. Each property stands out for its beauty, its location, the interior decoration and the level of service. You can choose a charming agriturismo cottage, a stunning villa with private pool, an exclusive fully staffed luxury villa or a historical castle with pool.
Browse each of the following estates in Tuscany to find out more about the available rentals, their location and surroundings and the suggested services.


The fortified hilltop village Barberino Val d’Elsa lies in the heart of the famous Chianti area, a region stretching between Florence and Siena. The Palazzo available for rent sleeps 16.

Castelnuovo Tancredi

A 600-hectare organic estate with rolling hills of vineyards, olive groves, grain fields and mature forests between Montalcino and Siena. On the estate is a beautifully restored farmhouse.


A beautiful estate at the entrance to a medieval hilltop town, it houses two villas which can be rented together or separately. The larger one can welcome up to six guests and has a large pool within a terraced garden. The smaller is a charming cottage for two with its own plunge pool.


The Chiarentana estate extends over the Val d’Orcia, a miraculously unspoilt valley in south of Siena, listed as UNESCO world heritage since 2004. The beautifully restored holiday apartments in the main Chiarentana building sleep 2 to 6 people, the converted farmhouses with private pools sleep from 6 to 14.


The Tuscan hamlet houses five impeccably designed villas for 4, 6 and 8 guests for a total of 30 guests. Each stylish villa features five-star amenities, an eclectic mix of antique and eccentric furniture, and meticulously maintained gardens.


Tucked away into the hills of Arezzo lies the magic Galbino property, a large and welcoming family estate with castle for 19 guests, gatehouse, farmhouses and all. Ideally located to visit TuscanyUmbria and the Marches.

La Badia

“I had a farm in Tuscany…” The famous line out of “Out of Africa” could just as well apply to this romantic estate near Lucignano between Arezzo and Siena, only one hour south of Florence. The beautifully converted farmhouse with pool can be rented with 7 beds or 10 beds.


La Foce

The property of La Foce extends over the hills overlooking the Val d’Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage. The beautifully restored holiday apartments in a castle sleep 2 to 4 people, the magical farmhouses with private pools sleep from 6 to 14. The luxurious villa of La Foce with its magnificent gardens has up to 19 beds.

The Le Gore estate has one villa available for rent - La Tartaruga
Le Gore

A six-hectare estate at the foot of a medieval town. It has two separate villas, one which is private and the other which can be rented, nestled within an olive grove and natural vegetation.

Le Rocchette

Le Rocchette is a small estate near the village of Lucignano, half way between Arezzo and Siena. The main house sleeps either 4 or 6 guests, and has a private pool. Cool design by the Italian owner, who has lived in Brazil and runs a charity program in India.

Arriving at the San Polo estate, a beautifully restored hamlet.
San Polo in Rosso

A vast 800-acre estate in the heart of Chianti dotted with rolling vineyards, olive groves and forests. Crowning a hill is a private medieval hamlet comprised of a fortified castle, ancient church, an 18th century villa and several beautifully restored farmhouses.

Tenuta di Gracciano

The Gracciano estate, one of the most renowned producers of the Vino Nobile di Montepulciano, lies one hour south of Florence in the lush Chiana valley. The restored farmhouse with pool with 8 to 10 beds is the perfect base to explore the surrounding Tuscany landmarks.

Via del Pellegrino

Via Del Pellegrino is the visionary project of the talented couple Giorgio and Ilaria Miani. The restoration of their 4 stunning luxury villas has taken rental villas in Tuscany to the next level.

Villa Gioli

In the summers of a century ago aristocrats and academics of Pisa retreated to their patrician country residences rising on the gentle hillsides shouldering their city. The villa with pool, halfway between Florence and Pisa with 12 beds is an example of these foregone times.

Vivo d'Orcia

“Vivo d’Orcia is not a place, it is a way of life…” The Castle of Vivo d’Orcia lies in the widespread Orcia valley in southern Tuscany, just one hour south of Siena, overlooking the Orcia valley, listed by the Unesco as a world heritage. The stylish agriturismo cottages on this estate have 2, 4 and 8 beds.


the cradle of the Renaissance

Because Tuscany is the cradle of the Renaissance (late 14th to early 16th centuries) its towns cast a spell like no other. You walk through Florence, Sienna and Pisa in a daydream, looking up. Between majestic palaces and outsize domes, there are so many treasures to marvel at. A maze of a thousand and one backstreets, the magic of countless squares, fountains dotted here and there: everything is an invitation to dream and to a delightful interlude. As you wander through Tuscany, you lose yourself in it.
But Tuscany is the region of a thousand and one hills too. Its breath-taking landscapes will make you want to roam the countryside and race down its valleys; and on the hilltops, you will discover perfect medieval gems: the villages of San Gimignano and Volterra will plunge you straight back into the Middle-Ages. In Montepulciano, Montalcino and in the Chianti region more generally, you will at last savour inimitable wines such as the famous Brunello or the Chianti classico.

Geographical Landmarks in Tuscany

Covering an area of 23,000 km2, Tuscany is bordered by the mountainous Apennine range and by the Apuan Alps to the north, while the river Arno flows through it from East to West.
You should travel through Tuscany, which is divided into 10 provinces, from East to West if you want to discover all of its riches. -The North East is home to beautiful, unrivalled Florence (380,000 inhabitants), the capital of Tuscany.c -Further south, the Chianti Region abounds with little medieval villages like San Gimignano or Volterra and you chance upon majestic Sienna (55,000 inhabitants), Florence’s old rival.
-South of Sienna, Montepulciano and Montalcino are renowned for their inimitable wines, while the Orcia valley is a Unesco World Heritage site.
-In the North-East, discover Pisa and Lucca, whose quiet charm will bewitch you.

A Brief History of Tuscany

It was in Italy, and specifically in Tuscany, that the exceptional era of the Renaissance began in the 15th century. The period was characterised by great economic and artistic prosperity and Florence was its dazzling incarnation. Thanks to a very wealthy banking family, the Medici, Florence acquired a wealth of artistic treasures. Today, the city is a UNESCO World Heritage site.
The Middle Ages were also a very prosperous period for Tuscany. In spite of incessant strife and of the Great Plague, which carried off half of the population between 1348 and 1349, the textile industry and trade brought wealth to the towns. Tuscan architects threw themselves straight away into the construction of daring and elaborate buildings.

Countryside, Nature and Walks in the Tuscan Hills

The CRETE region
South-East of Sienna, you will discover a hilly, clayey, region which offers a delightful variety of landscapes: peaks topped by a few solitary cypresses, a succession of hills disappearing into the mist, gentle slopes or sheer ravines carved by soil erosion. The most beautiful of these valleys, the Val d’Orcia valley, is a UNESCO World Heritage site.
Starting from Florence or Sienna, hire a car and take a few days to discover this region of the CRETE, whose name means “clay” in Tuscan dialect.

The MASSA and CARRARA region
Looking up at the mountains that dominate Carrara, at the foot of the Apuan Alps, you might think that you see the snow line: in reality, the glimpses of white are the marble and the huge quarries that dominate their slopes. The purity of Carrara’s white marble is unequalled, and it is here that Michelangelo would come to choose his marble.

Around Florence, go for a walk in FIESOLE
Perched on hilltops, between the valleys of the Arno and the Mugnone, Fiesole’s lush valleys and olive groves will delight you. You will also happen upon a spectacular panoramic view of Florence. Set off for a walk or a nice picnic in the open air.

> Find out what to do with your children while in Tuscany

Culture, Architecture, Art in Tuscany

-In Florence, don’t miss the Piazza del Duomo, the Piazza della Signoria, the Piazza della Repubblica, the Uffizi Gallery, the Piazza San Marco, the Piazza di Sante Croce, the Pitti palace and the famous Ponte Veccchio. If you have children with you, go the Parco delle Cascine, to the west of Santa Maria Novella station: it’s a very big, delightful public park. There is also a merry-go-round in the centre of the Piazza della Repubblica, which is a permanent feature.

-In Siena, go the Piazza del Campo (Palazzo Comunale, Torre de Mangia), to the Piazza del Duomo, home to one of Italy’s most beautiful Gothic cathedrals and the Chiesa di San Domenico. Make sure to note that’s it’s on the Campo square that the famous horse race, called the Palio, takes place twice a year.

-In Pisa, go to the Piazza dei Miracoli, one of the most beautiful squares in the world: you will gaze at some of the finest jewels of Romanesque art: the cathedral, the baptistery and, of course, the Leaning Tower.

-In Lucca, a city founded by the Etruscans, don’t miss the climb up the 207 steps of the Pallazzo Guinigi, from where you will enjoy a splendid view of the city. Visit the cathedral, built in both the Romanesque (11th century building) and Gothic (14th century renovation) styles. Go and see the authentic Romanesque Chiesa di San Michele in Forno too, as well as the Palazzo Mansi, a magnificent tribute to the Rococo movement, and walk along the ramparts that surround the town for three kilometres.

Tuscan Gastronomy

In Tuscany, you sample the Brunello de Montalcino, which cannot be ignored, and the Nobile de Montepulciano. But you can’t miss the Chianti classico, harvested on the dry hillsides between Florence and Sienna. It’s among the best Italian wines, fine but firm, with a ruby-red colouring and a powerful aroma. Distinguished, full-bodied, well-balanced, it improves significantly with age.
There are organised tours of the vineyards and wine cellars. It’s up to you to choose your favourite wine route: Vernaccia di San Gimignano, Nobile di Montepulciano, Terre di Arezzo, etc.
Local Produce
You must absolutely try Tuscan bread, extra-virgin olive oil, Prosciutto Crudo (uncooked ham), Pecorino Toscano (ewe’s milk cheese), Tuscan sausage, Colonnata bacon, honey from Lunigiana, chestnuts, and Panforte (gingerbread with almonds and dried fruit) from Sienna.
Gastronomic specialities
Every province abounds with specialities.
In Florence, try steak Fiorentina-style.
In Sienna, feast on lentil and pheasant soup, game croutons, or else the famous chickpea pasta.
In Pisa, allow yourself to be tempted by the white bean soup and by all the fish dishes (cod, hake…)

Shopping in Tuscany

In Italy, and especially in Tuscany, you will find leather goods of outstanding quality, shoes, gastronomic specialities, very good wine, or else jewellery.

Do not hesitate to go in to the factory outlets that are sometimes found in the heart of commercial centres.
You will come across luxury brands at very attractive prices. A few addresses:
– In Florence: COIN DEPARTMENT STORE (shoes), and MERCATO CENTRALE (flea-market)

You will also find plenty of open-air markets in which it is possible to find fashionable clothing and brand-name accessories. Take the time to browse there.

Finally, if you like pottery, you will find some very pretty pieces in Florence in the Via Faenza.

In our Blog Katharina’s Italy you can find first hand information and stories about Tuscany.