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Step away from the tourist trap of Plaka and descend into the historic underworld of Athens. In the shadow of the Parthenon, Psyri’s litany of excellent bars are prime territory for drinking like a local. Greek dancing, optional.

Young locals clad in leather jackets and Dr Martens laugh, smoke and sip microbrews on the cobbles of Psyri. The neighbourhood’s dilapidated buildings – once leather shops and typesetters – are lovingly adorned with bold graffiti tags, while street food vendors hawk souvlaki and pizza by the slice. Dive bars hide at the bottom of staircases invisible to the untrained eye, and music blares from darkly glittering speakeasy-style joints. Upon first look, this could be the trademark hipster neighbourhood now obligatory in any large European city, be it Berlin, Istanbul or Manchester. Yet a quick glance upwards leaves you in no doubt as to your location, for atop a nearby hill stands the Parthenon, its white Pentelic marble gleaming in the sun.

Psyri earned its anti-establishment reputation long before it transformed into a hip nightspot. Indeed, the working class neighbourhood was once terrorised by resident gangs, placing it right at the heart of the murky Athenian underworld.

In the 19th century, the cobbles of Psyri would have echoed with the step of the long, sharp-toed, high-heeled boots worn by the Koutsavadkides. This gang stalked the neighbourhood in their trademark ensemble: tight trousers, jackets worn with one arm out of the sleeve, and a broad sash to hide their weapons. Athenians were terrified of these fabulously dressed criminals – and so were the police. Much like in the Greek capital’s anarchist neighbourhood of Exarchia today, the district was avoided by law enforcement officers, leaving the Koutsavadkides effectively in charge of Psyri for over 50 years.

If you’d wandered the streets of Psyri during the rule of the Koutsavadkides, you’d also have had to dodge the “rock fights” that were a popular form of entertainment among the working classes during this era. Typically, the participants would meet at a pre-arranged time and sling insults at each other. Then the rocks would start flying as spectators cheered, and the injured became local heroes.

Had you ducked into any of the district’s tavernas – perhaps to avoid stone missiles – you may well have stumbled upon groups of revolutionaries plotting and whispering. With its anti-establishment reputation and lack of police presence, Psyri provided the perfect hideout for rebels during the early-19th-century Greek War of Independence. Leaving the taverna after sundown, you’d likely be greeted by the saccharine notes of a love ballad sung by a lovestruck young suitor below the balcony of his beloved.

It’s hard not to wonder what roving rogue Lord Byron – who briefly lived in Psyri in 1810 – would have thought of the area’s gang culture. However, he was perhaps more distracted by the 12-year-old daughter of his landlady – the muse for his famed Maid of Athens, Ere We Part poem. Rumour has it he later tried (and failed) to buy the girl for £500.

As the 1800s drew to a close, Psyri’s gang culture came to a sudden halt with the introduction of a new crime-fighting initiative, founded in order to end the reign of the fearsome Koutsavadkides. The officers would cut the toes from the gangsters’ trademark pointed boots, and the unused sleeve from their coats, shave their moustaches, and break their guns. It worked: the Koutsavadkides were humiliated and faded into obscurity. Next on the hit list were the district’s romancers. Officers would break their guitars over their heads before throwing them in jail for the evening.

Since then, Psyri has largely been a peaceful district, but has never managed to shake its anti-establishment vibe. Even today, visitors strolling its streets and drinking in Psyri’s litany of excellent bars can get a taste of the area’s gritty past – albeit without the threat of being mugged by a sash-wearing gangster.

Psyri’s leafy main square – Platia Iroon – is its most touristy area and a safe bet for the start of a pub crawl. In the corner of the square sits BeerTime, a simple bar filled with chunky wooden furniture and an extensive list of Greek craft brews.

Fairy-tale-inspired Little Kook, just off the square on Karaiskaki Street, provides a truly dazzling drinking experience, complete with cake. This sugary establishment is bedecked with innumerable fairy lights and larger-than-life fantasy decorations year-round. Previous displays here have included circus and Mary Poppins themes – with actors, too – and it’s always particularly over the top at Christmas.

For a relaxed afternoon beer, it’s difficult to beat Barrett. Located on Protogenous Street, it’s a firm favourite among young Athenians and Macbook-wielding digital nomads. This painfully hip watering hole features overstuffed couches, an indie rock soundtrack and an ever-present student crowd spilling out onto the pavement. Stone walls and a polished wooden bar keep the decor minimalist, while its status as an exhibition space means there’s always something interesting – and usually provocative – to stare at on the walls.

Just around the corner on Miaouli is Old Fashioned, a tiny, evocative hole in the wall brimming with trinkets and retro art. Locals slump along the bar under dim, low-hanging lamps, and every drink comes with a bowl of gargantuan stuffed olives. The bar staff here are always up for a chat and, even if you just pop in for a cocktail, you’re likely to be lured into staying until the small hours of the morning.

For a glamorous evening spent sipping champagne, Juan Rodriguez Bar on Pallados Street is a must. One of the most renowned bars in Psyri, this unapologetically ritzy establishment is decorated with the gilded frames, chandeliers and table lamps of the 1920s. The look is complemented by well-mannered waiters in suits. This sublime bar is a true treat, and a dramatic departure from the district’s other, grittier watering holes.

Down the street, Arodou provides a lively end to the night. In the small hours it hosts live music acts, with a skew towards Greek rock. The whole bar inevitably gets involved, with genuinely good singers regularly hauled from the audience to accompany the band, and – if you’re lucky – some authentic Greek dancing.

Psyri’s oft-gritty aesthetic may not be postcard-perfect Athens, but you don’t have to venture far to find a district that is. The narrow marble streets of tourist trap Plaka sprawl in the shadow of the Acropolis, lined with boutique stores and cutesy cafés. Nearby Monastiraki is packed with iconic, ancient landmarks, while Kolonaki brims with upscale shops and fine dining restaurants. Yet you won’t find many Athenians dining in the expensive, polished eateries that pack these districts. If you like to party with the locals, descend to the former underworld of Athens. Just leave your sharp-toed boots at home.

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