This bar has front-row seats overlooking Europe's loveliest square, the shell-shaped Campo in all its medieval glory. Whether Il Palio is a suntrap or a tourist trap doesn't really matter: it's simply the place to be, especially at sunset. This is the perfect terrace for sundowners, coffee or liqueurs. Ignore the touristy food and focus on the setting. Sip a spritz, classic cocktail or crisp white wine whilst watching the swallows soar and soaking up the cityscape. Here you can sense the Sienese in all their smugness.

Set on the main drag en route to the Campo, this café is a magnet for the cocktail crowd. Via Banchi di Sopra is a staging post on the classic evening stroll, so call in at Caffe del Corso for a drink, even its decent pizzas might persuade waverers to make a night of it. The mood changes as night falls with lingering coffee-drinkers giving way to a more fun-loving crowd.

Siena's 16th century fortress is home to a weighty wine bar and upmarket restaurant. The intriguing fortification is also a venue for the Siena Jazz festival in summer. The lounge bar is the setting for serious wine-tasting sessions, but you can just opt for rustic Tuscan treats, especially cheeses and cold cuts, washed down with well-selected plonk, sipped on the summery terrace.

This celebrated bar and pasticceria (pastry shop) is run by the Nannini dynasty. Tuck into its Christmassy panforte, a rich, exotic cake bursting with honey, almonds, hazelnuts, candied peel, nutmeg and cinnamon. Panpepato (a darker version of panforte) is even spicier. The sugar-coated, almond-scented ricciarelli biscuits here are far lighter. It's not clear what St Lawrence, the Sienese saint of sweets, would make of rock star Gianna Nannini, whose family runs this traditional pastry shop that's open till late.

Choose between cocktails and a cup of tea in this retro people-watching spot. By day, it's a civilised retreat for afternoon tea where locals loll like pashas on vintage sofas, sipping Assam and oriental exoticism. Then the eclectic teapots go back in the vaulted Aladdin's Cave, tea segues into cocktails (and more cakes) and soon it's rum and late-night jazz around the grand piano. Set near Piazza del Mercato, this softly-lit spot is particularly appealing for a winter nightcap.

This is Siena's beacon of excellence, both a classical music venue and a renowned music school. Set in a former medieval palazzo (watchtower), La Chigiana is also deeply Sienese. The institution masterminds winter classical concerts as well as two summer festivals, the Settimana Musicale in July and the Estate Musicale Chigiana in July and August.

This 16th-century theatre is set inside the Palazzo Pubblico, the seat of the Sienese Council. This is the most historic setting for classical music, opera, dance and drama. The interior is dashingly resplendent with four tiers of regal boxes, soft burgundy chairs and a charitable restoration from the 1950s.

This is Siena's second major theatre, staging Italian and foreign drama (in Italian) as well as ballet and musicals. With room to seat nearly 500, this grand theatre is another magnificent ode to sincere renovation in Siena, after much of it was damaged in WWII.

This superb ice cream parlour is what passes for decadence in sleepy Siena. This 'pure' Piedmontese brand seduces with healthy Sicilian lemons and hand-picked hazelnuts, with naughty nougat toppings and lashings of whipped cream. Grom stays open until midnight on summer weekends.