Hamburg is perpetually on the brink of falling out with itself. On the one hand, it’s a city of convention and millionaires – Hamburg has the highest concentration in Germany – with all the associated trappings.

But Hamburg’s alternative side is in rude health and full voice too. Ranging from seediness and vice all the way to seething anti-establishment protest, here’s how to experience the full gamut of Hamburg’s edginess for yourself.

1. Take the rough with the sleaze

Your flight here was probably half-full with stag-do-goers, their sights set on the bawdy bars and brothels of the 1km-long Reeperbahn. Hamburg’s Kiez – as the red-light district is known here – has made a long career of chewing men up and spitting them out. Even the Beatles (who spent their professionally formative years in Hamburg) had their eyes opened by “Sin Mile”.

But it’s also a tourist destination for those with no interest in titillation. Come for the people-watching alone: you could fill a novel with the gritty stories and characters associated with venues such as Zum Silbersack bar and Mojo Club.

You can also ignore the sex entirely – many locals do. The St. Pauli Theater overlooks the Reeperbahn, studiously ignoring the goings-on before it, while the Kiez also boasts Cuneo, one of the city’s finest Italian restaurants.

Red Light district, HamburgThe world through my eyes/Flickr

2. Embrace the skull and crossbones in St. Pauli

The Reeperbahn may be located in the St. Pauli neighbourhood, but this area doubles as the beating heart of Hamburg’s anti-establishment identity. The local football team, with its skull and crossbones regalia, is the most visible symbol of this attitude, and FC St. Pauli’s culture of punk, tolerance and anti-establishment resistance is tremendously refreshing. Catch a game if you can.

Step off the Reeperbahn and the mood changes utterly. St. Pauli is a peaceful, leafy, village-like place down streets such as Wohlwillstrasse and Grüner Jäger. On the former you’ll find St. Pauli’s tourist office, which looks like a minimal, artfully dishevelled café-cum-art space. Its gift items include indie bands playing cards, vegan and Fairtrade products, and badges depicting a Swastika-crushing fist.

If you’re a music lover (or even if you’re not), a Beatles-themed tour of the district is a must.

Skull and cross bones in St PauliMartin Abegglen/Flickr

3. Commune with communal living

St. Pauli is home to the Jägerpassage, a courtyard off Wohlwillstrasse where John Lennon had the photo taken for his Rock ‘n’ Roll album. With toys and other domestic paraphernalia lying around, it’s as if the courtyard’s flats have been turned inside out: you’re looking at an example of Hamburg’s particularly bohemian way with communal living. Called “Wohnprojekt”, these buildings were squatted in the 1980s and eventually allocated to the squatters by the city.

While the Jägerpassage is essentially residential, another of Hamburg’s squatting hubs, the Gängeviertel, welcomes visitors for tours. It’s reminiscent of what the Chinese call a “nail house”– homes whose residents refuse to bow to development, so that a motorway or mall or some other imposing development has to be built around it.

In this case, the squatting artists moved in when development stalled because of the financial crash. What they’ve produced is a pleasing visual mess of bunting and shrubbery, bicycles and ragged art, mannequin limbs sticking out of walls, graffiti and grubbiness, smack bang in the city centre. The counterculturalists use innovative ways to duck and dive bureaucracy – and the developers – not least by presenting everything to do with the site as art (the bar, for example, was termed a “Contemporary Drinks Museum”).

St Pauli, HamburgNeil McQuillian

4. Scratch your flea market itch

The Schanzenviertel – known as the Schanze – lies just to the north of St. Pauli. Here, on Schulterblatt, you’ll find the Rote Flora site, the most resonant symbol of Hamburg’s countercultural, leftist-anarchist identity.

Originally a theatre, Rote Flora was subsequently a cinema and department store before squatters occupied it in the late 1980s. Any attempt to change this state of affairs is met with heated opposition. You can get chatting to some of the Schanze’s alternatives by visiting the popular Saturday-morning flea market.

Rota Florawww.glynlowe.com/Flickr

5. Hang with Hamburg’s musos

Separated from the Schanze by the city’s former abattoir, the Karolinenviertel neighbourhood is undergoing a lurch towards gentrification. That said, it’s still a place of vintage stores and veggie grub, awash with a bohemian vibe.

Things are grittiest in the immediate environs of rock venue Knust on Neuer Kamp. This is one of Germany’s music hubs, a home for indie record labels and vinyl stores – check out Groove City and hip hop-inspired Gefundenes Fressen, purveyors of Hamburg soul food.

Karolinenviertel, HamburgSteffi Reichert/Flickr

6. Freak out at a festival

The city’s countercultural force is given joyful vent in the city’s festivals. The fantastic Internationales Sommerfestival – one of Europe’s largest contemporary performance arts festivals – is set to mystify the city with its wonderful weirdness for much of August. There’ll be site-based events but also an array of avant-garde interventions disrupting the city’s everyday.

Hamburg’s most popular conventional attraction is its Miniature Wonderland, full of tiny scale models. The Sommerfestival’s director, András Siebold, says that they’ll be having one of those too – but theirs is going to have rioters, he promises.

Hamburg's Internationales SommerfestivalCaroline Hayeur/Kampnagel.de

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