There's usually a piper playing on Princes Street, kilted in tartan, his tune rising through the cold air towards Edinburgh Castle high on the hill above. If you don't fall in love with Edinburgh at that very moment, there's something wrong. This beautiful, charming city has all of the Scottish cliches, from the pipers to the castle, the warm pubs to the narrow, cobbled streets. And they're all good.
This is fairytale Bohemia, a quaint little town of Gothic spires and Baroque churches, of pubs and restaurants, cobbled lanes and alleyways, and a river that carves a wide U-shape throughout the whole UNESCO heritage-listed area. Cesky Krumlov's only downfall is that its allure has been well and truly discovered by the world's travellers.
If you've seen the TV show Portlandia, you know what to expect: bearded hipsters and their knitted-jumper-wearing partners peddling organic vegan muffins to people who've just seen a really cool band you've never heard of before. But despite its dabbles with ridiculousness, Portland is a genuinely friendly, laidback city which has some of America's best coffee, food, music and arts scenes.
Things don't always work they way they should in Buenos Aires. Workers go on strike. Protesters block roads. Taxi drivers try to rip you off. But even with that – and maybe even because of it – you have to love Buenos Aires. You have to love the passion. You have to love the steak, the wine, the architecture, the fashion, the tango … And, of course, the football.
If you don't get lost in Stonetown, then you probably haven't left your hotel. This island capital, with its history of Arab, Persian, Portuguese and African colonisation, is a mind-boggling warren of narrow alleyways and tiny streets, where cars can never go, and tourists can never find their way out. Fortunately, the locals are usually on hand to help.
There's a ramshackle charm to the place they call "Valpo", a city built on steep hills that rise high from the oceanfront, a town of brightly painted houses often embellished with street art, a place of world-class boutique hotels and character-filled bars and restaurants. Valparaiso, essentially, is everything the nearby city of Santiago is not.
Luang Prabang can sometimes look just like any south-east Asian city: it's chaotic, a wild mix of tuk-tuks, scooters and pedestrians fighting for their slice of pavement or road. But there's more to this place. There are the sprawling complexes of heritage-listed Buddhist temples. There are the monks in their bright orange robes. There's colonial architecture. There are French wine bars and bakeries. Not your average city at all.
It doesn't have the temples and ryokans of nearby Kyoto. It doesn't have the same level of bright lights and bustle as Tokyo. But what Osaka does have is character. Character, and a seemingly insatiable appetite for good food. Even parochial Japanese from across the country will admit that Osaka has the best food around. From okonomiyaki to takoyaki, yakitori to perfectly steamed crab – what's not to love?
The Alhambra, the Moorish palace sitting atop Granada's highest hill, is nice enough. The city's many cathedrals are also pretty impressive. But you haven't experienced Granada until you've been out at night, until you've hung out at its bars drinking fine wine and eating free plates of tapas, until you've listened to live music and watched old men spontaneously bursting into song. This is a city that knows how to socialise.
It's not French, but it sort of is. It's not Canadian, either, if you ask most of the residents. But what Montreal is, is extremely, unpretentiously, unaffectedly cool. From the bagel shops to the "smoked meat" joints, the art galleries to the music venues, the fashion boutiques to the cafes: it all just seems so effortless. And that, after all, is the secret to being cool.
See also: Where Thai food snobs go to eat
