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Siena travel guide

This Tuscan city is within easy reach of some of Italy’s most famous wine regions and an ideal base for visitors to the area. Let our expert’s guide give you the inside info on where to eat, drink and shop

Siena’s perfectly preserved medieval centre is a tangle of sloping streets that curve around the contours of its hills. The major sights, including the intricately decorated cathedral and grand Palazzo Pubblico (city hall) with its lofty Torre del Mangia, were built during the 13th and 14th centuries, when Siena flourished as a cultural centre and key stop on the Via Francigena pilgrimage route to Rome.

The city’s beating heart is its lovely shell-shaped piazza, Il Campo, where the famous Palio bareback horse race takes place twice each summer (on 2 July and 16 August). Far from a dry re-enactment, the Palio is deeply felt; the city’s contrada (‘district’) culture is a way of life and loyalty is visceral. Animal symbols identifying the 17 contradas (such as porcupine, panther, tortoise and dragon) are everywhere, making for some curious and colourful street art.

Another aspect of Siena’s appeal is the sense of the countryside never being far away: Campo means ‘field’ in Italian – there are sweeping panoramas aplenty and the city’s gardens feature olives and vines. It’s here that an exciting project, Senarum Vinea – to reintroduce rare native grapes and create the city’s own wine – has taken root.

While the 20 or so varieties that have been found within the city and identified by DNA analysis are planted at Orto de’ Pecci for purely educational purposes, at the Castel di Pugna winery resort 3km out of town, micro-vinification is underway with the most promising varieties. As Emanuele Fumi Cambi Gado, whose family has made wine here since the 13th century, says: ‘Of the six grapes selected, it’s Giacchè that’s giving the best results. We’re hoping to make a wine for Siena that’s completely different from the rest.’

Siena map

Caption: Decanter / Maggie Nelson

Research by the University of Siena into centuries-old documents and paintings has proved invaluable for the project. In Ambrogio Lorenzetti’s celebrated 14th-century Allegory of Good Government masterpiece portraying local life, the prominence of vines is remarkable. The fresco also features a black-girdled Cinta Senese pig, the ancient breed that’s now returned to popularity on menus. Try it at Antica Salumeria Salvini just outside the city centre. Chianina beef is another local favourite for steaks and stews, though there is plenty for non-meat eaters too, with tasty pulse dishes and sheep’s cheeses, not to mention a spectacular range of spicy sweets.

On the wine front, Siena is perfectly placed for forays into beautiful and prestigious wine areas, where Sangiovese dominates in all its incarnations. One of Italy’s biggest stars, Brunello di Montalcino, is made just 40km south of Siena, and the walled medieval town of San Gimignano, with its famous towers and Vernaccia white wine speciality, is the same distance in the opposite direction. Meanwhile, Montepulciano, where Vino Nobile is made, is 60km away and Chianti is all around.

At the charming resort winery Castello di Fonterutoli, the Mazzei family is among the key players of Chianti Classico, making top-quality wines for 600 years and dedicated to ongoing Sangiovese research. This summer sees the second release (2018 vintage) of its Chianti Classico Gran Selezione trio from three different terroirs, including the impressive Vicoregio 36, which incorporates 36 biotypes of Sangiovese.

As Elisa Romei of Siena Wine Service points out, however: ‘There’s much more to Siena’s wine scene than the famous DOCGs.’ An expert in tours, tips and tastings, she loves sharing secrets on lesser-known wines. One to explore is the Grance Senesi, a tiny DOC area south of Siena with a handful of wineries, most notably the Monte Oliveto Maggiore monastery. Try its 1319 Sangiovese-Cabernet-Merlot blend, named after the year the abbey was founded.


My top 10 things to do in Siena

Cantina del Brunello

As you might guess from the name of his shop, Federico Pieri specialises in Montalcino’s famous wine. While he also stocks an exceptional range of other labels including rarities from throughout Tuscany and beyond, he loves nothing more than making new discoveries at small, little-known wineries. Book for a tasting in the Etruscan cave beneath the store.


Compagnia dei Vinattieri

A list of about 1,500 different wines, an ancient cellar carved into the rock and a menu of beautifully presented dishes such as rabbit, guinea fowl and octopus make any meal here a memorable one. End with the house speciality chocolate cake and a Moscadello di Montalcino dessert wine.


Grotto di Santa Canterina da Bagoga

A local favourite, run since 1973 by chef Bagoga (a nickname meaning ‘apricot’ in his native Montalcino) and son Francesco, and featuring brick arches and Palio paraphernalia recalling Bagoga’s brief career as a Palio rider. Dishes include peposo, a peppery Chianina beef stew that’s perfect with the restaurant’s own-produced Brunello di Montalcino.

Grotto di Santa Caterina da Bagoga Siena

Grotto di Santa Caterina da Bagoga


Il Battistero

This small wine shop opposite the cathedral’s 14th-century baptistery combines a historic palazzo setting with stylish contemporary decor and friendly service. Book for a tasting in the evocative medieval cellar and then stay over in one of the seven bedrooms. It also runs an all-day bistro on the same small piazza.


Il Salotto del Vino

A wine shop just off the Campo with an appealing interior incorporating contemporary style into a historic context. Owner Francesco’s passion for Pinot Nero has led to a section dedicated to Tuscan versions and he’s recently started producing his own five-grape spumante. He also runs the Osteria Bargello bar-eatery opposite.


All’Orto de’ Pecci

Take a stroll for a taste of the countryside within the city. All the varieties involved in Siena’s historic vines project are grown here, and there are farm animals and wide grassy lawns. Picnics are not allowed, but the farmhouse restaurant, run by a social cooperative, specialises in pizza and home-produced veg.


Osteria Il Grattacielo

A highly atmospheric, informal eatery dating from 1840, with a tiny interior, friendly service and tables under the arches outside. Daily specials vary and there’s a deli-style counter with lots of veg, cheeses and local charcuterie: don’t miss the fennel seed-flavoured salami, Finocchiona.


Osteria Il Vinaio

Brothers Bobbe and Davide run their popular all-day eatery with enthusiasm. There’s a lively, market-place atmosphere and a traditional menu including local speciality pici pasta with Cinta Senese pork. Ingredients are from small-scale Tuscan producers, there’s a good choice of Chianti and the four wines by the carafe include Rosso di Montalcino and Bolgheri Superiore.


Panificio Il Magnifico

Lorenzo Rossi’s historic bakery is the place for an authentic taste of Siena’s seductively spicy sweet treats: chewy panforte, cavallucci biscuits with walnuts, aniseed, pepper and ginger, plus pan co’ santi fruit bread and snowflake-soft almond ricciarelli. Ask for a drop of vin santo, perfect with such delights.


Siena Tartufi

Join Alessandro Pellegrini and his dogs on a truffle-hunting trip out of town or visit his shop to buy fresh truffles and products made with them. The most prestigious white variety is found in autumn, but other types span most of the year.


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