Beautiful on the inside: Ugly cities you should visit

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If you've ever eaten a Picnic chocolate bar or seen a Steve Buscemi film or watched Carlos Tevez play football, then you will understand: ugly is beautiful. Just because it ain't nice to look at, doesn't mean it has no value.

This rule extends to holiday destinations, too. Sure you can swoon over your Parisian lanes and your Riviera vistas, your Rocky Mountain highs and Peruvian pampa lows, but some of the best travel destinations in the world are also the ugliest.

The following cities may not rule your Instagram feed, and some are kind of dangerous and occasionally unpleasant, but they're certainly worth calling into and finding out that while beauty might be skin-deep, culture, vibrancy and excitement go all the way to the bone.

Mexico City

This hideous sprawl of a city has a bad reputation that's not entirely unfounded – it can be dangerous. But it can also be vibrant, lively and hugely entertaining. Eat "tacos al pastor" from a street vendor, go to a lucha libre fight at a local auditorium, see Diego Rivera's amazing murals at Palacio de Bellas Artes, or drink fancy cocktails on the rooftop at Hotel Condesa DF. Now you're getting it.

Berlin

It depends on your version of beauty. If you see graffiti as mindless vandalism, a blight on society, then you'll despise Berlin. If, however, you see value in street art, on social commentary ranging from four-storey-high murals to the scrawled number "6" throughout the city, then you'll love it. Berlin can look shabby and rundown in places, but this is a city with soul, and it doesn't take much more than a scratch of the surface to discover it.

Mumbai

You have to work hard to find an Indian city that could be described as pretty – maybe Udaipur would fit the bill, or Jaisalmer. The country's monstrous metropolises, however, are often eyesores of urban chaos, and Mumbai is little different. But that doesn't mean you shouldn't go. With Bollywood flair and a conglomeration of Indian culture at its soul, in a city inhabited by the country's rich and famous alongside the poorest of its poor, there's never a dull moment in Mumbai.

Beijing

Beijing might not actually be ugly, but it's hard to see it to make an informed decision. That's because the city rests under a constant blanket of smog, a choking, omnipresent cloud. Underneath it, and within it, however, you'll find joy. You'll find joy in the narrow hutong lanes, in the world-renowned historical sights, in the street food markets and antique stalls, in the gallery hub of the 798 Art Zone. Beijing is one of the world's great cities – it's just hard to see it at first.

Naples

Much like Berlin, this Italian city is covered in graffiti, although more of it falls into the "mindless scrawl" category here than "street art". There's also rubbish lining the streets and cigarette butts on top of them. Give it a chance, however, and you'll soon find that within Naples beats a good heart, a friendly heart, a passionate heart. Whether that passion is directed towards SSC Napoli, the local football team, or pizza, the local obsession, or just an argument with someone who cut you off on their scooter, there's plenty happening here, and plenty to love about life in Naples.

Tehran

Often rated among the worst cities in the world to call home, Tehran is about as attractive as a dropped pie. The traffic is ridiculous, the pavements dangerous, and there's usually smog. There's also, however, a network of great teashops to hunt out, plus the historic Golestan Palace, the gold and jewellery collection at the Treasury of National Jewels, and the sweet relief of Niavaran Park. There's a lot to love about Tehran – it's just that appearance isn't one of them.

Glasgow

The Melbourne to Edinburgh's Sydney, this Scottish city is often maligned as the country's ugly sister, but Glasgow has enough culture and personality to make it a worthy contender as Scotland's most enjoyable destination. Like Melbourne, it may take a while to discover Glasgow's true joys, which include a thriving live music scene, great pubs and bars, a huge amount of arts spaces, and a surprisingly good food scene. But it's worth the trouble. The only downside is that you'll have no idea what anyone's saying.

Phnom Penh

With a riverside location and a few palaces here and there, you could almost expect the Cambodian capital to be pretty. But you'd be wrong. PP suffers from the usual south-east Asian combination of scooter-heavy traffic chaos and a lack of decent pavements, but that doesn't mean it isn't enjoyable. This city is all about local life, from the bustling markets to the street stalls to the kids playing "jianzi" – a mix of hacky sack and badminton – down by the Tonle Sap river at night. And besides, any city that has a restaurant called Chuck Norris Dim Sum is OK by us.

Moscow

While St Petersburg is most tourists' established favourite in Russia, there's plenty to be said for Moscow, the big bad capital with its social realist architecture and urban sprawl of endless grey apartment blocks. For beauty, go underground, to the city's richly decorated Metro system. For historical significance, stroll past the Lubyanka, the old KGB headquarters, or visit the Kremlin. There's vibrancy to Moscow, an edginess that can't be matched by any other Russian city.

Sao Paulo

Flying over Sao Paulo, it's as if the city will never end, such is the enormity of its dirty urban sprawl. Indeed, Sao Paulo's richer citizens choose to commute by air, getting around the city in a buzzing swarm of helicopter traffic. On the ground it's manic, and occasionally dangerous. It's also, however, a lot of fun. Eat mortadella sandwiches at Mercado Municipal; go dancing and caipirinha drinking in Vila Madalena; check out the street art scene throughout the city; sample the best Japanese food this side of Tokyo; or see a football game at Pacaembu. Maybe just don't do it alone.