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Visiting Vienna at night dispelled the city’s stuffy daytime atmosphere.Mike Clegg/Getty Images/iStockphoto

Dispatch is a series of first-person stories from the road. Readers can share their experiences, from the sublime to the strange.

One of my favourite travel habits started out as a mistake.

I was 21 and Eurailing, revelling in how unplanned everything could be. I spent a month just showing up at train stations in Europe, looking at departure boards, seeing where sounded cool and hopping aboard. I'd go from train station to hostel, drop my bags and explore. It worked well for three weeks. Then I hit Berlin. I showed up at the most popular hostel and it was full. I went to the slightly rattier one, which was also full. By the time I tried and failed at the fifth hostel, it was about 11 p.m. and I was forced to admit that I wasn't going to have a place to stay for the night. I panicked, checked my finances and panicked again: not enough for even a cheap hotel.

It's okay, I told myself. This is all part of travelling. This'll be the story I tell.

So I decided to wander.

It got tough and I got tired forcing myself to find the places that were still open at 1 a.m. or 4 a.m. But, as I've found since, there are always places open at 1 or 4, and they're almost never the places you would have gone into if there were other options. This night crawling wrenches you out of traveller reflexes and clichés.

Getting to know a city at night, all night, ups the ante – pushing you into an acquaintance with other sides of the city you're in, sometimes darker and seedier, sometimes just hidden and unexpected. If travel is a process of exposing yourself to new things and pushing your boundaries, these all-nighters act as a sort of hyper-travel.

Now, I do it all the time, mostly intentionally. I book an overnight layover, landing in the evening. I store my bag at the airport or a central train-station locker and explore until I take off the next morning. There are usually no extra airline fees and no hotel-room costs, so it's like a bonus trip, a cherry on top of your vacation.

I'd been to Vienna twice before, spending an overnight layover between Sofia and Toronto, and I wasn't impressed with the general stuffiness of this once great imperial capital. Then I wandered its late-night/early morning streets. The tourists turned in and time stretched out in front of me. With hours of no obvious place to go, I wandered down residential streets, saw student apartments with band posters on the walls and family apartments with dusty blinds and kitten statues in the windows. I watched the sun rise on a bench in an empty park, birds chirping, a bicycle squeaking unhurriedly past, and I saw Vienna through new eyes. Vienna tries to convince tourists it's still firmly planted in its 18th-century glory days but, when you pull back the bed clothes, it's actually a fully functioning 21st-century city. I've been back three times since, and it's now one of my favourites.

I've also rifled through the entrails of New York's pre-Bloomberg Times Square and got to appreciate the uniqueness of a place where – as a result of the theatre and restaurants, strip clubs and porn shops, high-end bars and dive bars – members of every social and economic class had an excuse to be in the same place at the same time.

I've discovered the cascade of bibulous nighttime shelter that is created by Dublin's liquor laws, with its different closing times for pubs, bars and clubs. Nightclubbers spit out around 3 a.m. end up at the Dame Café, part of a late-night convenience store and, when that closes at 4, you and everyone else are funnelled into the McDonald's on Grafton Street, which closes at 5.

Just this summer, I Eurailed again for the first time since college, drawn by this year's addition of Eastern Europe to the pass's repertoire. It was a 10-day, nine-nation sort of a trip, so time was precious, and stealing an extra eight or 10 hours by not getting a room in Krakow, Poland, a city I knew practically nothing about, gave me time to discover its surprisingly raucous sledz (herring) and vodka scene, acquaint myself with the weird pink umbrella ladies who try to lure businessmen into basement clubs where other ladies sit on their laps and have their way with their wallets. I got a sense of the city that I wouldn't have found going from museum to shop to cute perogy restaurant during the day.

I know I'll be tired by 6 a.m., and the adrenalin really wears off by 8, when the rest of the city starts revving up. So I make sure my flight, train or bus – preferably something with reclining seats – leaves no later than 9 or 10.

Night crawling through cities is not that different from staying up all night with an acquaintance. It creates the sort of intimacy that can lead to a deeper friendship, or plant the seeds of a lasting love.

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