Where to stay

La Bagnaia Set within what was once a medieval village, dating back to 800BC, this elegant golf and spa resort is still owned by its original family. The ancient chapel is in action, too, and the resort offers fine Tuscan cooking within its La Voliera restaurant. Doubles from £89. Strada Statale, 00 39 0577 813000, curiolabagnaia.com

Borgo Scopeto Relais This stylishly converted historic hamlet offers breathtaking views of Siena’s skyline. Set in a 485ha wine estate, your home is within the small cluster of refurbished buildings surrounding the 18th-century farmhouse. Doubles from £210. Siena-Vagliagli 18, Castelnuovo, 00 39 0577 320001, borgoscopetorelais.it

Campo Regio Relais Right in the heart of Siena, with marble floors and frescoed walls, the building dates back to the 16th century, making the views almost as good looking in as they are looking out. Doubles from £134. Via della Sapienza 25, 00 39 0577 222073, camporegio.com

Castel Monastero Amid the vineyards and forests of Siena, you’ll find Castel Monastero, a restored medieval village and monastery, complete with a 13th-century cellar and a spa. With a keen focus on food and wine, they also offer white truffle hunting trips. Doubles from £350. Monastero d’Ombrone, 00 39 0577 570570, castelmonastero.com

Croce di Bibbiano On the site of a former monastery, these seven Tuscan-stone apartments fit perfectly into the landscape. Flanked by rolling hills and cypress trees, they’re rustic in style, some featuring pools. Owned by a winemaker the food offering is excellent. Doubles from £80. Località Bibbiano 1/3, Poggibonsi, 00 39 0577 958918, crocedibibbiano.it

The Grand Hotel Continental The city’s only five-star pad is just metres from the Piazza del Campo, where the Palio takes place, and set within a 17th-century palazzo. Stay for a night just for the experience and eat at its award-winning fine diner Sapor di Vino. Doubles from £200. Via Dei Banchi Di Sopra, 00 39 0577 56011, grandhotelcontinentalsiena.com

Travel Information

Siena is both a province and city in central Italy’s Tuscany region, distinguished by its medieval brick buildings and known internationally for its Palio di Siena horse race. Time is one hour ahead of GMT. Currency is the euro (EUR). Flight time from London to Florence is 2.5 hours. From here, the 85km train journey to Siena takes 1.5 hours. In October, the average high temperature is 19C and the average low is 13C.

GETTING THERE

Alitalia offers regular direct flights from London Heathrow Airport to Leonardo da Vinci International Airport, Florence. alitalia.com

easyJet flies from London Gatwick and Luton to Florence. easyjet.com

RESOURCES

Terre di Siena is the official tourist board and its website is packed with useful information to help you plan your trip. terresiena.it

FURTHER READING

Every Day in Tuscany: Seasons of an Italian Life by Frances Mayes (Broadway Paperbacks, £7.99), draws us back to this glorious part of the world, 20 years after the runaway success of her Under the Tuscan Sun. Still clearly besotted by Italy – her house, the fragrant geraniums, the warmth of her neighbours and, of course, the food – Mayes lovingly documents it all in what might be her best memoir yet.

CARBON COUNTING

To offset your carbon emissions when travelling to Siena, visit climatecare.org and make a donation. Return flights from London produce 0.40 tonnes of C02, meaning a cost to offset of £2.98.

Where to eat

Prices are per person for three courses, unless otherwise stated

Azienda Agricola Montechariano Informal and set within a rustic hilltop farm. You need to ring ahead to book, but will be rewarded with juicy Florentine steak, homemade wine and generous local dishes made by the owner Mario. From £45. Strada Monte Chiaro 35, 00 39 0577 363442 La Bottega del 30 Michelin-starred restaurant in the Tuscan hills, around 30 minutes from Siena. Having held a star for more than 20 years, it’s the area’s must-visit. Expect elegant presentation, bold flavour and a cellar of some 350 bins. Tasting menu from £95pp. Via Santa Caterina 2, Villa a Sesta, Castelnuovo Berardenga, 00 39 0577 359226, labottegadel30.it

La Voliera Poised in a plush resort, chef Alessandro Chiesa knows how to get the best out of the local produce. His porchetta is sublimely sweet and served with a rich sauce, the pici pasta boasts the ideal bite while the menu offers some of the more delicate niceties that fine diners expect. From £65. Strada Statale, 00 39 0577 813000, curiolabagnaia.com

Osteria le Logge Cosy local joint down a narrow medieval street off the main piazza. Opened in 1977 by husband-and-wife team Gianni and Laura Brunell, expect rich bucatini with wild boar ragù and tender steak Florentine. More elegant, artistic dishes inspired by the Tuscan larder are also offered. From £46. Via del Porrione, 33, 00 39 0577 48013, osterialogge.it

Ristorante Arnolfo Set within a 17th-century Tuscan palace 20 minutes from the city, this two-star restaurant has some of finest plates in the region. Family run, with only 30 covers, expect superb local produce including meat and fish from the Tyrrhenian Coast. Excellent wine cellar. From £109. Via XX Settembre, 50, Colle di Val d’Elsa, 00 39 0577 920549, arnolfo.com

Ristorante Croce di Bibbiano A spectacular dining room – owned by a winemaker – overlooking undulating vineyards. Most of the ingredients are grown or reared on site. From £40. Località Bibbiano 1/3, Poggibonsi Siena, 00 39 0577 958918, crocedibibbiano.it

Ristorante Particolare di Siena A modern restaurant under the medieval city walls with all the look and feel of contemporary dining with the chefs eager to impress with their culinary art. While Michelin having already taken note, Siena is still at its heart: think fillet of Cinta Senese prosciutto, Chianina tartare with tapioca, gin, cucumber and an elixir of rose sorbet. From £26. Via Baldassarre Peruzzi, 26, 00 39 0577 1793209, particolaredisiena.com

Food Glossary

Aquacotta

Tuscan vegetable soup enriched with poached egg

Bistecca alla Fiorentina

Florentine T-bone steak taken from the loin of the young steer (vitellone) which has the fillet on one side and the sirloin on the other. It’s normally 3-4cm thick, weighing around 1.5-2kg. For this cut, the Chianina is the choice cattle breed

Castagnaccio

Traditional cake made with chestnut flour

Cavallucci

A thick, round biscuit, with a distinct taste of aniseand candied orange. The name roughly translates as ‘little horses’

Chianina

Tuscan breed of cow, once used primarily to work theland, which gives a lean, strongly flavoured meat

Chianti

A wine region in Tuscany known for its fruity reds, madeup mostly from sangiovese, the predominant grape in the area

Cinta Senese

Local pig breed of ancient origin that roam free across the region. Their diet consists of chestnuts, fruit and woodland finds

Crostini Toscani

Antipasti dish – rounds of toasted, baguette-style bread generously topped with a chicken liver, caper and anchovy paste

Lampredotto sandwich

Lampredotto is the fourth stomach ofthe cow, which is cooked in a broth and then served with salsaverde and/or a rich, spicy sauce in a focaccia-style bun

Panforte

The famed chewy Italian dessert with all the flavoursof the festive season, containing lots of fruit and nuts

Panzanella

Cold bread salad whose name derives from the word pan, short for pane or bread, and zanella, an old Italian name for a bowl. The salad contains unsalted bread, tomatoes, red onions, basil and olive oil

Pappa al pomodoro

A soup made with hunks of stale Tuscanbread, tomatoes garlic and basil leaves

Pici

Hand-rolled Tuscan pasta variety that’s thicker than spaghetti. The preferred way to serve it locally is alongside wild boar ragù

Ribollita

This hearty bread soup is one of the most popular dishes in Tuscany and contains cabbage, cannellini beans, onions and carrots

Ricciarelli

A type of macaroon, strong in almond flavour, dating back to 14th-century Siena. Popular at Christmas, served with sweet wine

Food and Travel Review

Two dogs yap at the wheels of the tractor as Mario Machetti trundles his way up a dusty track, overgrown with vines. ‘That one is Bart and that one is Lola,’ he says, dismounting his steed to introduce us to his four-legged followers. ‘I named her after my first girlfriend.’ Machetti’s hilltop farm is everything that’s good about Siena, the most central of Tuscan provinces, and it starts with the view. His home is a landscape of hills that crisscross each other to form a countryside that seems to forever fold in on itself. Here and there the green is broken with specks of terracotta – the rooftop of a farmhouse or church, perhaps a little cluster of a village.

That is until your eye turns to the city of Siena, in the distance; a collective of sun-changing browns, yellows and reds, rising above the green rug. Even from where we stand, a good 30-minute drive away, the 102m, grey marble Torre del Mangia tower is clearly seen, elegantly cutting through the crowd of tiles to rise above it all.

From a bathtub-turned-planter, Machetti plucks strawberries as he talks to us. His small patch of Siena may seem ramshackle in the quaintest, most rustic of ways, but he uses every bit of it to grow, rear and cultivate things to eat or drink. Chubby chickens stroll past, as we head to what a chef would call a kitchen garden. Garlic, tomatoes, root vegetables, every leaf you can imagine – it’s not easy to see where one ends and another begins. ‘We’ve got everything that’s important in life right here,’ he says. ‘Wine, olives, meat and vegetables – the four staples of life.’

Next to his veg patch is the olive grove, between them assorted farming equipment of the vintage that usually finds a home in a museum. ‘My dad used cows to pull his plough,’ Machetti explains, as he points to the relics. As we walk down the lane, we stroll past a tangle of sangiovese grapes (he’s got two hectares of vines in his 24-hectare plot). He prunes as he goes, until he has a handful of greenery, which he feeds to the next friend we meet. ‘Beautiful, aren’t they?’ he announces with pride, as we meet his herd of Chianina.

There are 20 cows, 20 calves and one bull, Warrior. ‘He’s only been with us for a year, we had to sell the other one because he was too old. For me they are the best beef flavour,’ Machetti explains. ‘The taste is so strong because they are lean, there’s no fat on them, so it’s just big meaty flavour – the ribs are my favourite.’

Walking back through the rows of vines, Lola in tow, to his farmhouse at the top of the hill, Machetti introduces us to Gino. ‘He’s been with me for a long time. I only have two people here who work for me, Gino and Antonella – she does everything around the kitchen except for the barbecue, which is my domain.’

His on-site ‘restaurant’ works on something of an ad hoc basis. As he and Antonella are always in situ, along with his wife Simonetta, there are no set hours. You simply call up and, for £45 per person, Mario cooks you up a feast. In the most literal sense. When we sit down for lunch, Antonella pours homemade red wine from a giant flagon. Machetti’s vessel? A tankard. ‘My dad used to drink two litres a day,’ he laughs, as he sips from his pint.

Good wine is everywhere, this is chianti heartland, but if you own vines, you have your own wine, and Machetti’s is almost a self-expression: it’s full of flavour, with so much fruit it’s like drinking a bowl of cherries and raspberries drenched in purée.

In myriad forms, the spoils of the land fill the table, from the wine, to vibrant salads, bruschetta made with his own olive oil and roughly cut tomatoes, and a carpaccio that’s both sweet and hearty.

The smell of the charcoal grill fills the room, before Machetti places a giant steak Florentine, at least 4cm thick, onto the flame. ‘The Chianina were raised to work in the fields, and then farmers would use them for the second purpose,’ he explains, as he cuts thick slices of perfectly charred, caramelised, smoky steak. It’s more delicate than he had led us to believe, still lean and strong, but not overpowering. With the cows no longer pulling the ploughs across the land, the following generations must have sweetened up somewhat in their retirement.

The story of Machetti’s Chianina rings true to Alessandro Chiesa, a Siena-born chef who recently returned home from stints in Italy’s big cities to cook up his favourite dishes at La Voliera restaurant, a 20-minute drive west. ‘Chianina is such good-quality meat, if you get the fire right, you just need a little salt and rosemary oil,’ he says.

On the restaurant’s alfresco terrace, the chef talks about the local food. The plate in front of us is painfully delicate, in the way that the Michelin inspectors love, with different elements jutting out like a multicoloured, multi-textured, edible art installation. Amid the angles and curls, leaves, petals and purées, there are purple potatoes, white asparagus, courgette flowers, carrots, heirloom tomatoes, peppers and even verbena. It’s pretty, but entirely misleading as to what Tuscan food is all about.

Even the chef serving this cornucopia of seasonal vegetables knows it’s about far more robust plates than this. For instance, the wholesome ribollita (vegetable and bread soup) that follows, which is full of so much good stuff that only now do I believe what my mum told me about eating my vegetables – I feel like I’ve added a year to my life after just one bowl. ‘This soup changes with the season and where abouts you are in Tuscany,’ says Chiesa. ‘It’s just whatever you can find in the area and what’s in season. You just throw it all in.’

Chiesa’s own home is only a few miles from the La Voliera, itself based at a hotel set on what was once a medieval village. ‘Every village around here has its own recipe,’ he continues. ‘For example, there’s peposo, a stew which started in a village where everyone worked with pottery, so they used the clay ovens to cook the dish each day. They’d combine beef, onions, red wine and black pepper in a pot and pop it in the kiln before they went about their work. It would be ready when they finished.

‘This is how we got fagioli el fiasco [a dish of beans cooked in a flask],’ explains Chiesa. ‘The farmers used to put the beans inside a chianti bottle along with water, plenty of garlic and sage, then close it up, put it in the fire and let the charcoal go to work.

When they came back at night, the beans were ready to eat.’ Even in the modern day, the same dishes pervade the region, though few with as much regularity as pici, the famed thick, hand-rolled pasta that we’re served next.

Hand-stretched, they resemble rope-like twists, thicker than spaghetti, with just the right amount of bite. Woven within is a wild boar ragù cooked in red wine with rosemary, juniper and sage, adding a richness that’s well balanced with the leggy, al dente pasta. ‘We still eat local,’ he says of his sourcing. ‘We’re a very rural region; our quality is so much better than anywhere else.’

Proving the point further is the finale, an eight-hour, slow-cooked porchetta in veal jus. The sweet, delicate meat packs the kind of porkie punch you only get from something cooked in a manner that keeps the flavour within and not left in the tray behind.

Andrea Bezzini knows his pigs, better than even Chiesa. His family have been guardians of the Cinta Senese, Siena’s native breed, since the 1800s. They’ve done so from the same house, too, in Simignano, a tiny village west of the city. Once home to 750 people, today its miniature maze of streets housing just 35. After brief introductions, he takes us to see his beloved family.

Like a rioting piggy football team, adorned in a black kit with pink hoops, the Cinta Senese flood the hillside, trotting eagerly towards Bezzini. They can roam free across some 420ha, gaining almost their entire year’s diet purely from what falls, but they know that he’s going to show them where the good stuff is. He always does.

Around 100ha is filled with their favourite sustenance: chestnut trees. Armed with a wooden stick for the occasional shoo, Bezzini steers them across a field full of wild sage and buttercups, the air thick with the aroma of mint, to a woodland full of fallen chestnuts. ‘They eat with the seasons,’ he tells us. ‘In September they get apples and peaches, then from October it’s chestnuts and acorns. They last until February because when the leaves fall, they cover the nuts to keep them fresh, the pigs just snuffle them out.’

A plate of prosciutto di Cinta Senese is proffered at one of the bars during Siena city’s happy hour. Stop for an aperitivo after work (or a day’s holidaymaking), and you can get involved in a spread of all the local favourites. And it’s not just the local meats and tapenades, but its sensational cheese, too. Boasting a Pecorino for every occasion – cellar-aged, cave-aged, salty, sweet, creamy, tart, nutty – the cheese stall is where you go to chat, find out all the gossip, and fill your bag with multiple varieties.

The hottest gossip in Siena is that of the Palio. For a city of little more than 50,000 people, twice a year it both divides and unites. Split into 17 neighbourhoods, or contrada, Siena’s medieval square, Piazza del Campo, is covered with sand and transformed into a race track. The entire city gathers for two races – one in July, one in August – where 10 horses, each representing a contrada, are ridden for three laps. ‘The race is everything,’ one bar owner tells us as he hands over a negroni. ‘Your contrada means everything to you, it is your life, and the Palio is what brings us all together – we hate our neighbours for those days, but we’re friends again after.’

The Palio is uniquely Sienese and, for a city whose people knew centuries of war, fighting against the likes of fierce rival Florence, it’s their differences that makes them proud. In a shadow cast long from Florence, Siena has always stood up. It’s matched it in battles (ask about Montaperti); in its architecture – one look at the Duomo, a giant ice palace-meets-Russian chessboard of a building is case in point; and in its food and wine. Now, it’s beating them when it comes to beer. Ironically, with one named after Florence’s own – Dante.

La Diana is Siena’s only craft brewer and characters from Dante’s Inferno provide the names for each one its styles. ‘Dante wrote of how there was the mythical river flowing underneath Siena that we could never find,’ explains brewmaster Francesco Mazzuoli. ‘So it seemed a fitting name for us.’ A challenge almost as big as finding a non-existent source of water, is selling craft beer to Italians. ‘We have no culture for beer in Italy,’ he says. ‘We are in the land of wine. If people order a beer, it can be any beer. You’d never just ask for wine, it’s red, white or rosé, different grapes, different flavours.’

La Diana’s take on Belgian, wheat, IPA and APA styles is brought to life with Sienese ingredients. They’ve used wild hops grown within the city walls, and the defining ingredient, honey, is unique, too. ‘It’s sweet, but not too sweet,’ says Mazzuoli, ‘a little bit eucalyptus, but not too strong. It’s soft. Like a flower, but with spice.’

They’ve even worked with legendary panforte baker Lorenzo Rossi to create a beer – Piccarda – that uses his traditional recipe to make the ultimate festive ale. ‘This is Siena in a bottle,’ Rossi tells us of the beer, at his shop in the city centre. The shop has been making Siena’s best biscuits, pastries, sweets and cakes since 1952. Rossi, who took over from his father 20 years ago, talks us through the ricciarelli (macaroon-like biscuits), cantucci (Tuscan biscotti), candied fruits, almond-sugar ratios and the ingredients he uses. But it’s always his panforte – a spiced, chewy wheel crammed with dried fruit – that is best known. ‘Panforte is full of herbs and spices – it’s made to make you feel better. It’s an edible apothecary,’ he says. ‘It’s the alchemy of the ingredients that make it special.’

In some cases, very special indeed. ‘We had one particular customer, a man in his eighties, who came in and bought a panforte, and then returned to buy more, week after week. Eventually, we asked him what it was about it he liked so much and his wife started to blush – it turned out, it had an aphrodisiac effect. That’s the thing about Siena,’ continues Lorenzo. ‘We’re very proud, we’ve very close, and everything is about passion.’