Eating & Drinking
For rustic restaurants, take your pick between: Ristorante San Desiderio in an old church Grotto di Santa Caterina da Bagoga, a local favourite, run since 1973 Osteria Il Grattacielo, a highly atmospheric, informal eatery dating from 1840, with a tiny interior, friendly service and tables under the arches outside
La cantinetta di Rignana is a beautiful restaurant (you need a car to get there) with a marvellous view.
Seeing & Doing
The most secret thing you can probably do in the city? The ‘Bottini di Siena’- The underground aqueducts of the city which were built during medieval times to bring fresh water to the fountains located throughout the city.
The system still works to this day and if you’re lucky enough to get a tour, you can see the water flowing beneath your feet.
Next best thing: do a wine tasting underground. Other guided experiences of note: a private walking tour, a half day wine tour or a winery lunch ihe Tuscan countryside via vintage Fiat.
For shopping, Via di Città is a good place to start, especially for food – Manganelli 1879 (Via di Città 71-73; 0039 577 280002; closed Sunday) is one of Italy’s great delicatessens.
Quieter corners to explore include the streets towards Santa Maria dei Servi; around the Pinacoteca Nazionale; and to the northeast, around the church of San Francesco.
At Alessandro Stella‘s little boutique on Via Camollia, 45, you’ll find a range of impossibly chic handmade shoes, belts, and wallets for the seriously sartorially-minded gentleman.
Aloe & Wolf on Via del Porrione, 23, gorgeous vintage store.
Mag Boutique, located just a three-minute walk from Piazza del Campo on Via dei Termini, is a wonderful gem once highlighted by the New York Times in their 36-hour guide; women’s clothing, luxury candles, small gifts, beauty products, and more.
The main market in town takes place in the Fortezza Medicea on Wednesday mornings from 7am to 1pm. Stalls are set up around the Fortezza and La Lizza park and sell mostly clothes, leather goods, costume jewellery, some homewares, food products, and more. The same location hosts a small farmer’s market on Friday mornings, where you can find excellent bread, olive oil, fruit and vegetables, local products, cheeses etc.