Sparkling red stilettos caught my eye in the foyer of Teatro Comunale, and I glanced up to see a young woman in a ’20s swing dress looking immaculate.

I peered down at my own scruffy shoes. Among all these groomed Italians at the finale of the Charlie Chaplin Film festival, I stood out like a black olive on a margherita pizza. As Chaplin’s 1920s A Woman Of Paris flashed on the screen above, a live orchestra played the score and I marvelled at the opera theatre’s intricate gilded ceiling, dating back to 1763.

For many locals this was la dolce vita – to live in a city so rich in artistic and cultural history. Although I felt more akin to the students hanging outside the theatre dancing to a live DJ, Bologna – Emilia-Romagna’s cultural hub – wouldn’t be Bologna without its bohemia and bourgeoisie.

The blend can probably be dated back to 1088, when the city’s university opened – making it the oldest in all of Europe. Today the piazzas and porticoes (Bologna is famous for its columned arcades) are buzzing with the 114,000 students, giving the town a young, hip vibe against the backdrop of medieval architecture.

Perhaps the best example of this architecture is the Basilica of San Petronio, a massive church that dominates the central Piazza Maggiore. It was built in 1390 and boasts an astounding gothic interior, which seems to reach heaven.

Before entering the basilica look out for the building’s unfinished facade – while the church was originally intended to be larger than St Peter’s in Rome, money and land instead went to developing the university and the basilica lost out.

It follows that you’ll find part of the original university, today a library, just beside the Basilica. Pope Pius IV commissioned the Archiginnasio in 1561. Heraldic coat of arms and frescoes adorn the ceilings, which lead you to the Anatomy Theatre with its statues carved in cedar wood. Apollo, the god of medicine, overlooks the marble table in the centre of the theatre where the first public dissection of a corpse took place in 1315 (dissection was illegal at the time as the Catholics believed the body contained the soul). Bombing by the Allied Forces destroyed the theatre in World War II, but it’s been painstakingly reconstructed.

The university gives the town one of its nicknames – La Dotta, meaning the learned one. Another is La Rossa (the red one) after the terracotta tiles that roof Bologna’s older buildings and give the city a hazy, vibrant glow. You can get lost wandering through the medieval laneways of old Bologna, but whichever way you turn you’re likely to stumble upon the reason for Bologna’s other nickname – the fat one, or in Italian, La Grassa.

Ditta AF Tamburini is just one of the many shops selling Bolognese delicacies such as cured meats and salami, as well as mouth-watering local Parmesan cheese, which costs a third of the price in London’s Borough Market.

When it comes to food, the Bolognese are world experts. From tagliatelle al ragu (spaghetti bolognese is considered to be its poor imitation) to baloney – officially named IGA Mortadella di Bologna. Local handmade tortellini is far better than any you would taste from your local Tesco. Legend has it the tortellini was invented by an innkeeper who was dreaming of Venus and tried to recreate her naval, and you’ll see local women doing the same as you browse the shops.

Many restaurants, despite being in such a bustling city, still manage to retain that rustic feel.

Osteria Broccaindosso is a gem hidden behind a wooden door without a trace of signage. The owner Gianni, with his rounded belly and hearty laugh, welcomes diners with open arms and plates overflowing with culinary delights. It’s a typical Bolognese greeting, warm and friendly, regardless of whether you’re an immaculately dressed theatre goer or a scruffy tourist.

» Jo Cackett travelled to Bologna with the Tourist Board of Emilia-Romagna Region and stayed at the Golden Tulip Aemilia Hotel (

Love the neighbour
From the 11th to 13th centuries, families ruled the region of Emilia-Romagna and their main enemies were each other.
To defend themselves against other families they’d build tall towers throughout the city, and the bigger the tower the more powerful the family. Only two of the hundreds of towers built in Bologna remain. The tallest is Torre degli Asinelli, standing 97.6m high, and you can climb its 498 steps. The other is Torre Garisenda, which has a worrying 3m lean and is sensibly closed to the public.