Backing the right horse | Review: Castel Monastero, Tuscany


Joseph Hammond came to Siena to see its 800 year old horse race and found the real winner was a historic hotel in the Tuscan countryside

Backing the right horse | Review: Castel Monastero, Tuscany

The flag fluttering in the breeze outside the stone walls of the former monastery might have seemed like little more than a colourful nod to the hotel’s historic past. For those in the know, it was a secret message that Siena, a city in the heart of Tuscany was preparing for another running of its 800-year-old sporting event – the Palio di Siena.

To describe it as a horse race is unfair to an event which has elements of rugby, gang warfare and the Tournament of Roses Parade

Arriving after an international road-trip that dipped through Venice, San Marino, Rimini, and the edge of Lake Trasimeno where Hannibal trapped and massacred a large Roman Army in 217 B.C., we were in need of a good’s night sleep under sheets with more threads than we could count and launch our attack on some Tuscan culinary delights. One of my favourites is pici pasta,  a stout version of spaghetti usually unknown to Italians from elsewhere in Italy. Even in Florence, an hours drive away, finding some can be difficult.

Castel Monastero, Tuscany

Castel Monastero provided all that and more. Indeed if one can expect anything from a hotel that used to be a monastery, it’s peace.  This is a truly boutique hotel in an 11th-century building. Each room has a distinct rustic personality: Stone exteriors give way to leather couches, broad wooden desks that look out toward the hills, and wooden shutters.

The hotel is only a short drive from Siena, a charming Tuscan town and long-time rival of Florence. The annual football derby between the two cities isn’t held without some mention of the Battle of Montaperti in 1260 where a Sienese force outnumbered ther opposition by roughly 2-1 and proved triumphant. These days it seems most Italy visitors prefer Florence to Siena 2-1 which is a fantastic thing for those in the know. There are fewer tourists to elbow joust for gelato as one explores the historic town perched dramatically on several hills.

Castel Monastero

Staying at Castel Monastero, it is tempting to never leave the hotel and simply stare at the Tuscan hills which have inspired thinkers from Machiavelli to Plutarch. The landscape is populated by pretty vineyards, and a neighbouring property (also a former monastery) is now a winery.

The hotel itself is like a miniature version of Siena with a small piazza in its central courtyard.  Almost all towns in Italy have a piazza, but few as grand as that in Siena where the Palio di Siena horse race is held each year.  The hotel includes a small active chapel and sits on a large footprint which includes three outdoor pools which flow together and add a further calming element to the landscape. The spa includes special programmes in everything from weight loss to maternity and includes access to several indoor pools – one of which has the same salinity as the Dead Sea.

Castel Monastero

We didn’t come to Siena just to sleep and eat copious amounts of pici pasta, although I did plenty of that. I also came to see one of Siena’s most ancient traditions – the aforementioned Palio Di Siena. To describe it as a horse race is unfair to an event which has elements of rugby, gang warfare and the Tournament of Roses Parade.

Siena’s walled city is traditionally divided into 17 contradas or districts. For 800 years a horse race held twice each summer has served as a stand-in for open warfare in what must count as one of sport’s greatest rivalries.

The hotel embraces the tradition with the flags of the winning contrada flown outside its medieval stone walls. In the elegantly restored lobby, I spied a glass bowl filled with wooden lottery balls used in selecting the order for the Palio.

I waited until almost the last minute to leave the hotel on race day. The jockeys and their supporters spend hours before the race debating strategy. I spent mine floating in peaceful bliss in the otherwise empty spa.

The hotel has arguably some the best seats in the house – on the highest floor of a historic building which looks right down on the race without obstruction. When the race finishes, you can watch as the sun fades over those Tuscan hills as brave.

The race left me famished, and Castel Monastero has two inviting restaurants. One serves traditional Italian food in the former wine cellar called La Cantina. Above it is Contrada, a Gordon Ramsay restaurant that mixes Italian and Greek cuisine. At the tables around me in the palazzo of the hotel, guests discussed the race and the day’s events. Inside, there is a plush bar for guests to enjoy but on the night of the race, everyone seemed to prefer dinner and drinks under a Tuscan moon.

As I left the next morning, a different flag – flew above the hotel’s historic walls. The rivalry continues … C


Castel Monastero Monastero D’Ombrono, 19, 53019 Castelnuovo Berardenga SI, Italy Phone
 +39 0577 570570;