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Some of the most memorable moments in life are our ‘firsts’: our first time getting behind the wheel, going to a gig or kissing someone. But often the settings for such events – car parks, community centres, graffitied alleyways – don’t do them justice.

This got us thinking: if you had the chance to relive these pivotal moments anywhere in the world, where would be the perfect place to try them?

Inspired by – an anthology of 100 profound, moving and unforgettable travel experiences – we’ve paired some of life’s major milestones to settings suited to their significance.

First… drive

Many of us grew up fantasising about our first time getting behind the wheel, putting the pedal to the metal and screeching off into the sunset. The reality for most involved crawling in first gear around the empty car park of a local supermarket, with a parent or older sibling sitting rigidly in the passenger seat, sporadically stamping on an imaginary brake pedal.

If you could do it over: swap the supermarket for the wild mountain passes of Canada with a cruise along the Icefields Parkway. This wide public highway, based on an old packhorse trail once trudged by fur traders and First Nation communities, meanders for 143 epic miles through the heart of the Canadian Rockies, skirting around hulking, snow-scuffed mountains and thickets of forest that shimmer in the reflective waters of glacial lakes. While minimal traffic flow bodes well for newly qualified drivers, road tripping in this remote part of the world does come with its own unique hazards: grizzly bears.

Alternatives: for more wildlife-heavy road tripping (and minimal obstacles), consider a self-drive safari in Zambia. Meanwhile, equally jaw-dropping landscapes are prevalent along Argentina’s Ruta 40, which traverses 20 national parks as it winds down the length of the country.

First... kiss

Ah, the first kiss – a true minefield of a milestone. Whether yours was at a school disco, sweaty nightclub or student dormroom, the chances are the first time you locked lips with someone felt uncomfortable, awkward and a little… slobbery.

If you could do it over: first-time Frenchers can soothe both pre-smooch jitters and fear of excess moisture by watching dozens of people take part in the annual Omed-Omedan festival, also known as ‘the kissing ritual’, in the Balinese village of Sesetan. On the first day of Saka New Year, swarms of unmarried locals gather to publicly suck face in a bid to ward off bad luck and find love, before being unceremoniously drenched in water by priests keen to not let things get too heated. Once confident of your technique, head south to one of the Bukit Peninsula’s pristine stretches of sand – not a bad spot for a first kiss come sunset.

Alternatives: for something a little more traditional, consider the Pont Notre-Dame Bridge in Paris – ideally in the rain – or, for those looking for love, try the ‘Kissing Bench’, a landmark on Syracuse University campus, New York State. It’s said couples who kiss while sitting on the bench will one day wed.

First… tattoo

Whether that chinese symbol etched permanently into your arm was procured in a dubious high street studio, a ‘talented’ artist friend’s bedroom or forms the lasting memory of a week-long coming-of-age romp in one of Europe’s famed party towns, when it comes to tattoos, we don’t always get it right first time round.

If you could do it over: add a dab of gravitas to your first tattoo experience by getting inked at what’s thought to be the oldest tattoo parlour in the world. Located down a winding alleyway in Jerusalem’s Old City, is run by Wassim Razzouk, who proudly continues a 700-year-old family tradition of tattooing pilgrims who visit the holy city. While religious motifs remain the core of his work – with some designs based on hand-carved wooden stencils from the 16th century – travellers going under the needle in this atmospheric parlour can choose from a wide range of options or create their own design in advance.

Alternatives: more traditional tattooing techniques are on offer in parlours throughout Thailand, where bamboo tattoos (using pieces of sharp bamboo rather than an electric needle) are popular. Those lacking inspiration should consider heading to London’s annual tattoo convention, where over 400 international artists showcase their best body art skills.

First… concert

Everyone wishes the first gig they attended was some sort of seminal event writ large into musical folklore; Dylan going electric, Kurt Cobain headlining Reading Festival in a wheelchair – an impressive anecdote to whip out at work parties. But when all is said and done, your first live music experience likely involved a cover band at your local town hall, fronted by an overweight man sporting an ill-fitting Bon Jovi wig and a haunted look in his eyes.

If you could do it over: there are few more breathtaking venues in which to plunge into the world of live music than the Red Rocks Amphitheatre in Colorado. The hilltop venue has been moulded from a natural rock formation, with a stage and open-air seating venue nestled between two giant sandstone monoliths that provide exquisite acoustics. The one-of-a-kind venue has welcomed some of the world’s biggest artists over the years, including Jimi Hendrix, U2 and, notably, the Beatles as part of their first US tour. Today the distinguished setting attracts everything from jazz to EDM artists, all backed by views of the vast parkland with a star-flecked sky overhead.

Alternatives: to hear classical instruments sounding their very best head to the Tokyo Opera City Concert Hall; the venue is home to the Tokyo Philharmonic Orchestra and exalted for its legendary acoustics. Meanwhile, England’s world-famous Glastonbury Festival welcomes hundreds of live acts to its farmland venue during its weekend run, meaning you’re certain to stumble on at least one performance worth bragging about.

First… legal drink

Nothing says ‘adulthood’ like that initial glug of your first legal alcoholic beverage, even if it was a glass of cheap vino bought for you by an aging aunt in a sticky-floored local pub. Chances are that first dalliance with alcohol was forgettable, and not just because of the quantities consumed.

If you could do it over: Beer Day is celebrated annually in Iceland on March 1, the day that the country’s 74-year prohibition laws finally came to an end in 1989. Each year the anniversary of that fateful day is marked with great gusto by Icelanders: join the partygoers thronging Reykjavik's pubs, sample a celebratory swig of Brennivin (the country’s signature drink) atop Snæfellsjökull glacier or, for the quintessential Icelandic tourist experience, order a beer from the Blue Lagoon geothermal spa’s swim-up bar. ³§°ìá±ô (cheers) to that.

Alternatives: for hops and hedonism, join lederhosen-clad revellers celebrating Oktoberfest, the world’s largest beer festival, in Munich, Germany, or for something a little more small-scale, soak up the atmosphere of Dublin’s old-world pubs, where the local trad music scene is as intoxicating as the locally brewed Guinness.

First… trip abroad

For many, the annual family holiday is akin to a game of Monopoly: it seems to last forever, squabbles ensue over money and everyone wants to be the dog (who’s enviably been left at home). Of course, childhood trips provide mounds of cherished memories, but there’s more to life than sitting in a damp tent playing yet another game of rummy.

If you could do it over: the Grand Tour was a traditional rite of passage for wealthy young European (and later American) nobles during the 18th century. Those who could afford it would leave their homeland, often accompanied by a ‘bear-leader’ (chaperone), in an attempt to enlighten themselves by perusing the art galleries and frequenting the concert halls of Europe. Fortunately, in the 300 years since, travel around the continent has become far more accessible – with Interrail passes a perennially popular way to trundle between iconic cities – but no less rewarding. Stroll by the Seine in Paris, browse ramshackle bookstores in Amsterdam and gawp at ancient relics in Rome: let the education begin.

Alternatives: a beach break in Sri Lanka? Horseback riding in Kyrgyzstan? Following the Gringo Trail through South America? While it might be too late to do-over your first holiday, there are endless possibilities for your next.

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