Villas around Siena

Siena is architecturally and artistically one of Italy’s richest cities. Its planning is particularly enchanting; ancient red-brick walls enclose narrow streets which climb up and down the hills and curve unexpectedly into lively piazzas. The special harmony of architecture and colour, the character of the people, placed in such wonderful countryside, make Siena many peoples’ favourite city.

read more

italy > tuscany > siena


Sleeps: 16
€ 8107 - € 9577 per week.

italy > tuscany > pisa

Villa Amorosa

Sleeps: 14
€ 4000 - € 5500 per week.

italy > tuscany > siena

Podere Mandrie

Sleeps: 8
€ 3285 - € 4607 per week.

italy > tuscany > siena


Sleeps: 10
€ 3835 - € 6450 per week.

italy > tuscany > siena

Virginia B

Sleeps: 4
€ 800 - € 1100 per week.

italy > tuscany > siena

Virginia A

Sleeps: 4
€ 980 - € 1600 per week.

italy > tuscany > siena

Villa Luisa

Sleeps: 10
€ 1850 - € 3490 per week.

italy > tuscany > siena

Villa Donati

Sleeps: 14
€ 2140 - € 4400 per week.

italy > tuscany > siena


Sleeps: 8
€ 2567 - € 3851 per week.

italy > tuscany > siena

Ropoli Sotto

Sleeps: 6
€ 1000 - € 1850 per week.

italy > tuscany > siena

Ropoli Sopra

Sleeps: 4
€ 840 - € 1300 per week.

italy > tuscany > siena


Sleeps: 8
€ 1257 - € 2543 per week.

italy > tuscany > siena


Sleeps: 14
€ 7550 - € 12000 per week.

italy > tuscany > siena


Sleeps: 4
€ 1100 - € 1800 per week.

italy > tuscany > siena


Sleeps: 6
€ 1150 - € 2070 per week.

italy > tuscany > siena


Sleeps: 9
€ 2835 - € 4305 per week.

italy > tuscany > siena


Sleeps: 4
€ 1200 - € 2000 per week.

italy > tuscany > siena


Sleeps: 14
€ 2560 - € 3990 per week.

italy > tuscany > siena

Dan's House

Sleeps: 4
€ 800 - € 1067 per week.

italy > tuscany > siena


Sleeps: 3
€ 800 - € 1250 per week.

italy > tuscany > siena


Sleeps: 10
€ 5333 - € 6667 per week.

About Siena

History | Local Events around Siena | Best Museums in Siena | Beautiful Towns near Siena | Things to do around Siena | Typical Food and wine from Siena | Market Days close to Siena, Tuscany |Good Restaurants close to Siena

History of Siena

Siena started life as an Etruscan settlement, (c 900-400 BCE) inhabited by a tribe called the Saina. Later, during the reign of the Emperor Augustus (63 BCE to 14 CE), like many towns in Tuscany Siena became a Roman Colony "Saena Julia".

The Siena that we see today started to come into being in the 8th century, when the city was conquered by Charlemagne. The new Frankish lords married into the existing Sienese nobility and founded Abbeys that still stand today, like the beautiful Abbey of Sant'Antimo.

The Frankish connection also developed the pilgrimage and trading routes with Northern Europe. The development of the wool trade and of Siena as a centre for money lending would lead to Siena's golden age, largely considered to be between 1260 and 1348.

As Siena increased in size its peculiar siting and layout became more important: it has no large river running through it or by it, but was founded, presumably for defensive purposes, on a tripartite ridge of tufa rock. The city's ingenious solution to the lack of water was to carve over 25 kms of tunnels underground to collect rain and ground water. You can read about it (and organise a visit to this hidden marvel) here: Bottini in Siena.

As the city's influence increased it came into conflict with neighbouring Florence - also because Siena was harbouring Ghibelline refugees was the city. The two cities settled their differences at Montaperti with Siena's decisive victory in 1260. The name of the battle lives on and will still be hurled at Florentines in arguments, 760 years later!

The victory at Monaperti marked a surge in Siena's fortunes. Many of the cities famous figures and artists date from this period. Duccio di Buoninsegna, Simone Martini, the fabulous Lorenzetti brothers, Ambrogio and Pietro and many more.

In 1348 the Black Death visited Siena and laid waste the population. The city was building a new, larger Cathedral and the work was never finished. You can see what would have been the new nave by the Museo dell'Opera del Duomo and even climb to the top of the tall sliver of brickwork to get a fantastic view of the city.

After this blow to their population and finances, Siena went through a period of decline, relieved only after a century of a succession of councils, alliances and expulsions. The papacy of Enea Silvio Piccolomini marked a rise in prominence of the city - he became Pope Pius II in 1458. One of his legacies was the beautiful town of Pienza (named after himself) where, together with architect Bernardo Rossellino, he started to reshape the town as an ideal city.

By the early 16th century the city was in trouble again. During a period of civil unrest Charles V (Holy Roman Emperor, Archduke of Austria and King of Spain) sent a spanish garrison to take over the city. The Sienese expelled the garrison and Charles laid siege to the city. After 18 months Siena surrendered to Spain - this was the end of the Republic of Siena.

Local Events in and around Siena

The Palio

Perhaps Siena is most famous for the Palio, a bareback horse race run around the beautiful shell-shaped square, the Campo, twice a year, on first Sunday of July and on the 16 August. But this is more than a horse race, it is the culmination of year-round preparations for a tradition which has never faded, and which the Sienese take very seriously. A series of colourful and breathtaking medieval spectacles start four days before each race. The event is still heartfelt by the Sienese and it is not advisable to take small children to see it from the centre of the Piazza del Campo.

Piazza del Campo a Siena, Italy

Accademia Musicale Chigiana

The world-renowned Chigiana Music Accademy is situated in the notable Gothic Palazzo Chigi-Saracini. The academy organizes Master Classes in the major musical instruments as well as singing, conducting and composition. During the summer months a series of concerts are held under the title of Estate Musicale Chigiana.

Giostra di Simone

Giostra di Simone In early August - normally the first weekend - in the tiny hamlet of Montisi there is an annual festival to commemmorate the time the town threw out their feudal lord, Simone Cacciaconti, in the 13th century. It's a festival of food and wine with medieval re-enactments and costumes, the highlight of which is knights on horseback jousting a stuffed figure representing Lord Simon. Later tables are laid along the length of the village streets for a communal meal with dancing and singing. It's wonderful, we've been and it's a fantastic event.

Palio of Casole d'Elsa

Casole Palio In mid July the best village in Tuscany (that's Casole d'Elsa, where I grew up) has its very own Palio, a horse race up the hill below the village to settle which of the local hamlets is champion for the year. Food, flag waving and family fun make this a wonderful day out.

Best museums in Siena

There are some fantastic museums in Siena - here's a full list of the Museums and Sights in Siena

The great thing about museums in Siena is that they're housed in stunning buildings in their own right. I have two favourites:

Palazzo Pubblico

This is the building that faces the famous Piazza del Campo, surmounted by the impressively tall "Torre del Mangia". It is Siena's town hall - still is to this day. But it also has a fabulous collection of artworks, including the "Allegory of good government" by Ambrogio Lorenzetti and the "Maesta" by Duccio. Climbing the tower is great fun too.

Palazzo Pubblico in Siena

Museo di Santa Maria della Scala

The old hospital facing the Cathedral has been turned into a great museum, including a special children's section on the lower floors.


Beautiful towns near Siena

The area around Siena is one of the most beautiful landscapes of the world - and the villages and hilltop towns are wonderful to visit, stay in and enjoy. Here are our favourites:

Casole d'Elsa, Tuscany, Italy

1. Casole d'Elsa

This lovely hill town looks down on a patchwork of greenery and despite its small size has a lively village life with an art centre, restaurants, enoteca, ancient castle and friendly residents easy to interact with. There are concerts in the Romanesque Collegiata & festivals year round.

2. Monteriggioni

Built on its hillock in 1213 by the Sienese, Monteriggioni is undoubtedly the most classic fortified town in Tuscany. Its walled crown of towers is encircled by olive groves and one has but to step within its gates to feel what it would have been like to live on a small scale.

3. Pienza

Named after the Pope who re-created it according to Renaissance principles, Pienza has both splendid architecture and sweeping views of the Val d’Orcia. As the pecorino cheese capital of the region it is also delicious place to stop for a meal.

4. Montisi

Sprawled on a hilltop between the Val d’Orcia and the Crete Senese, Montisi is small village with a large heart. Off the beaten tourist track, it provides a glimpse into the life of a vibrant Tuscan community that knows how to entertain itself.

5. Montalcino

Dominated by a vast fortress that now hosts an excellent enoteca offering visitors the chance to taste the area’s prestige red wines, Brunello and Rosso di Montalcino, Montalcino is a charming town with spectacular vistas.

6. Sant'Antimo

Set against a backdrop of olive groves on a gently rising hillside, the Romanesque Benedictine Abbey of Sant’Antimo is but 10 km. from Montalcino. Built of golden travertine in the 12th C., its origins date to the time of Charlemagne. A balm for the weary.

Things to do around Siena

Ride a vintage steam train through the clay hills around Siena and the outer Val d’orgia. Traveling slowly on the Treno Natura thru this landscape is the best way to go.

Taste the Val d’Orcia’s premium wines. Montalcino’s Brunello and Montepulciano’s Vino Nobile are not inexpensive, but a sip or two will tell you if their fame is justified.

Sample pecorino at a cheese factory near Pienza. Not only will you learn something, but product sampling on site is practically a meal.

Listen to opera from the cathedral steps in San Gimignano Estate, the 3-month summer series of opera, poetry, theater, ballet and concerts in Piazza del Duomo. List of town’s events

Introduce children to the Middle Ages at the Archeodromo in the Parco della Fortezza Medicea in Poggibonsi. A on-going medieval settlement brought to life – fun & educational.

Get to know the Elsa River by crossing it and walking along its banks. The SentierElsa trail starting from Colle di Val d’Elsa is a wonderful woodland path, fascinating for the whole family.

Enjoy a modern antidote to too many ancient stones in San Gimignano’s Galleria Continua. This important contemporary art gallery has partners in Beijing, Havana and Les Moulins.

Typical Food and Wine in Siena

Being so close to the Chianti region results in many cuts of meat – beef or even wild boar – being braised or slowly stewed in red wine to produce Stracotto or Brasato al Chianti. A variation of this stew adds a head of garlic and a generous amount of pepper to produce Peposo. To accompany main courses popular side seasonal dishes feature Porcinimushrooms amassed by jealous collectors or Carciofi, the flexible artichoke that may be marinated, fried or stuffed.

To finish on a high, Tiramisù, literally a ‘pick me up’, is the ubiquitous cold coffee-flavoured dessert consisting of coffee-drenched ladyfingers layered with a whipped mixture of eggs, sugar and mascarpone cheese flavoured with cocoa. No wonder it’s the dessert of choice.

Market Days close to Siena, Tuscany

MONDAYS – Casole d’Elsa (1st & 3rd), Radicondoli (2nd & 4th)

TUESDAYS – Empoli, Poggibonsi, San Miniato, Gambassi Terme, Montespertoli

WEDNESDAYS – Barberino Val d’Elsa, Certaldo

THURSDAYS – Monteriggioni, San Gimignano, Empoli

FRIDAYS – Colle di Val d’Elsa, Montaione

SATURDAYS – Castelfiorentino, Certaldo, Staggia, Montespertoli

Good Restaurants close to Siena

Osteria Casolani– Casole d’Elsa, Tel: +39 0577 948733

La Pergola– Radicondoli, Tel: +39 0577 790717

Il Granaio – Radicondoli, Tel: +39 0577 550791 or 393 1033287

Bar dell’Orso – Monteriggioni, Tel: +39 0577 305074

Osteria Antico Travaglio – Monteriggioni, Tel: +39 0577 1651764

Ristorante Arnolfo – Colle di Val d’Elsa, Tel: +39 0577 920549

L’Antica Trattoria – Colle di Val d’Elsa, Tel: +39 0577 923747

Le Vecchie Mura – San Gimignano, Tel: +39 0577 940270

Osteria del Vicario – Certaldo Alto, Tel: 0571 667809

La Mangiatoia – San Gimignano, Tel: +39 0577 941094

C’era una Volta – Lucardo, Montespertoli, Tel: +39 0571 669578