Tip for you. When dining exclusively with ladies, never bring up the rumour that a certain American President’s mother was sired in an occult sex magick ritual in 1926 by the Great Mage, Aleister Crowley, over dinner. Specifically, tapas. It tends to belittle and demean the tone, apparently. That I should learn this lesson in the Southern hemisphere’s epicentre of style and class, Melbourne, was, maybe, fitting. My emergent priapism did not go unnoticed and led to my all-female travelling party debating the root of my obsession. Over breakfast the next morning, an inferiority complex was muted. Nailed, one might say.

Inferiority complexes can be dangerous things. History is littered with stories of poorly endowed, short men resorting to all manner of unpalatable behaviour in an attempt at what psychologists like to call transference. The Holocaust? Hitler was a shave under 5’7 and a failed artist. The Napoleonic Wars? Bonapartes, ahem, Little Bona was less than an 1812. On a tiny frame. Not tonight or any night, Josephine.

Countries who suffer from such afflictions can also pack a macho swagger, as an Englishman who’s spent any amount of time in Australia can attest. Of course, Gods Countrys only crime against humanity has been Paul Hogan and being annoyingly unsporting when winning at games of mild ball skill. And physically, one could hardly call it a wimp, even behind its back. Yet, the amateur shrink can detect a touch of the insecure braggart in Aussie trumpeting of their achievements and inherent qualities.

Which is not to say that they should be down on themselves. Because they have an awful lot to be proud of. Comparatively high standard of living, generally gorgeous weather, bountiful sources of barbecued protein and strapping, healthy, morally-ambiguous young women (there I go again). It’s all there. The problem they have is that it does tend to be there, as opposed to here. And it is a long way to go, especially considering the current strength of their dollar and the rise in oil prices.

Melbourne suffers from an own inferiority complex, all its own. In short, it’s not Sydney. Canberra was conceived only to break up these diametric sisters and be the dull one in the middle. Melbournites will tell you that Sydney is up itself and flash. Crass and gauche. A star fucker and a hanger-on. Whereas they are the bookish, hot, geek in thick-rimmed specs and a demure blouse, showing merely a hint of d’colletage. Who talks in French and understands Art and doesn’t think vintage clothes and objects are old peoples junk. Nouveau? No, no.

We’d all been flown in on Qatar Airways fabulous Business Class from London. This is about as civilised as long-distance flying gets. Some eight hours later, Melbourne’s class was showing through the gummy-eyed haze.

We walk the Lanes and Arcades around the central block of Bourke Street, led by the far too perky for this time of day Fiona Sweetman of Hidden Secrets walking tour. The secret in this case is not the President’s mother sired in Satanic lust, but many gorgeous, independent boutiques. This warren of narrow alleys interconnects the citys oft described American-style grid system a 19th century prototype of 12 blocks that could be San Francisco. In the spirit of egalitarianism that bore it, the rents have been fixed for years. Other cities take note. The sense of an organic culture, the beautifully-nuanced and competing vernacular aesthetics all of this is dying in London and New York.

Inflating the property market and encouraging the developers Utopian zeal kills such enticing, cool locations. Nowhere in The Smoke (except on the fringes of dodgy Dalston) would you find such self-created, self-funded creative businesses. Designers boutiques, speciality retailers, untouched Art Deco department stores, an amazingly vibrant cafe culture all thriving. If this was in the Northern Hemisphere, it’d end up the most fashionable postcode, impossibly hip, over run by money and eventually glassed over. Yes, Shoreditch, I’m talking to you.

A view shared by Steve Blick, an Ulsterman who made his name at Sohos Fish Hairdresing, followed a girl to Hong Kong and found himself here. His joint venture with a tailor and cobbler, Captains of Industry, is the exemplar. A creaky staircase, off an alley leads to a gorgeous cafe (every business in the Lanes sports a huge Italian coffee machine they’re addicted) on the first floor of a 1920s warehouse. Then, three side rooms house Herr Blick and his scissors, Thom Grogans fitting room and J.S Roberts lasts. The entire experience is elevated, relaxed and, like the furniture and fittings, totally old school. Blick maintains that he could never have pulled this off back home. Where are you going to find somewhere this size, location and central that is affordable?, he asks between snips. He doesn’t offer me something for the weekend.

The Hopetoun Tea Rooms is another example of quality living, maintained. Established in the Collins Street Block Arcade in 1892, its opulent reputation has been fully restored, thanks to the dedication of voluptuous ex-fashion PR, Kelly Koutoumanos. A time-capsule of Victorian jade wallpaper and huge etched mirrors, the window reveals elegant ladies, perched at tables, eyeing up their cream teas. Kelly, siren of confection, feeds me a sublime pecan tart. I’m smitten.

Other notable mentions go to Koko Black chocolatiers and the Degraves Subway Stations Campbell Arcade, a pink, art deco hub of shabby chic boutiques and home of the worlds only handmade zine museum, the Sticky Institute.

Having seen Melbourne from the ground, we take to the sky. Firstly, the Eureka Skydecks 88th floor viewing platform, where an 89th floor penthouse will set you back a whopping $10 million (these people don’t know they’re born). And then from the basket of a hot air balloon, piloted by Global Balloonings suitably dishy Argentine pilot. He starts talking about Robert Menzies secret transvestitism and the girls swoon. (I jest).

Barely any cities have the airspace or the will to let such rides drift dreamily over their centres. But then, that’s the kind of place Melbourne is. Classy. Coming down with barely a bump, we head to the Yarra Valley, 40 miles east and the citys own garden paradise. Victorias principal wine growing region, though not as prolific as South Australias Barossa Valley, with its Penfolds, Rockfords, Jacobs Creeks and Wolfsburgs, does punt some fabulous grog. Two years ago, deadly fires swept through the region a cataclysm big enough to earn the day the moniker Black Saturday. Ironically, though utterly biblical in its decimation, the fire left potash ripe for last years Winter deluges. The result is a landscape breathtakingly green and fecund (and un-Australian). Think Tolkiens Shire. Think bucolic Merry england.

Whereas Barossa is filled with German names, you will find some French ones here. Dominique Portet is the ninth generation of vigneron in his family, dating back to the 18th Century. Number 8 ran Chateau Lafite-Rothschild. Sauv Blancs, far less green than the Kiwis, delicious sparkling Fountain Rose and a pumping, structured Shiraz are the speciality. We do a blending class. I don’t take first prize for the challenge, because mine is roundly considered feminine in its fruitiness. I am asked by the winner how it feels to lose to a girl. I am now very conflicted.

To a fitting colonial experience for dinner at Chateau Yering, who’s restored accommodation buildings are a civilised wonder. Were guests of the management, so are treated to the chefs special attentions. In the filigreed dining room, Elenores, the food and wine pairings are spot on and everyone (including myself) is impeccably behaved. No one wears a tie.

We stay in the Yering Gorge Cottages, run by laconic local, Ross Stevens. The cottages are less cottage, more stilt-raised modernist A Frame. A great family location and a beautiful setting to hear Kangaroos mating ferociously, through the night. Next day, Ross takes us out to see the platypus play on the Yarras banks. They never got the memo. I do not mention the nocturnal marsupial love grunts, for fear of cementing what my father would call a reputation.

Other notable stop over includes the modernist glory of the TarraWarra Winery and its museum, filled with much notable local art, by owners Marc and Eva Besen. Quick note across Victoria, many of these gorgeous, and, in many cases architecturally fascinating destinations, seem to be owned by middle-aged, middle-class couples, not millionaire patrons. They are singularly created as retirement projects and as a creative outlet after years of hard toil. Quality of life is something that the New World still seems to be able to guarantee. The idyllic Bella Vedere restaurant and cooking school gets a gold star. Pairing a 12 quid caesar salad, with Yarra Yerings $95 Gruyere Pinot Noir 2008 is saucy and the oenological highlight of the trip.

Back to the city. We are staying at the Art Series Hotels. Three have opened so far across the south of the city, honouring significant Melbourne artists. The Olsen in South Yarra is dedicated to expressionist painter John Olsen. The Cullen, in Prahan, glories ironic young pretender, Adam Cullen and one of stars of the TarraWarra collection, the gothic and haunted Charles Blackman, gets his own hotel, too. The contemporary new builds, fashionable vibe and muted interiors contrast with the central districts colonial grandeur and act as a back drop for the art. Yet another pet project of a hard-working couple, made good, the hotels (they are rolling out into a chain) show how much Melbourne tries to project its indigenous creativity. Whether this civic zeal leaves room for an honest critique of the work, is a question to be answered another time. The beds are bloody sensational, though.

An hours drive to the Mornington Peninsular, the southern eastern Hamptons of Melbourne. Drinking and driving? Bad. Drinking and Riding? Very good.

A man (me) on a horse he can’t steer (a slow, steady Shire-cross, just in case) negotiating a summer sun-dappled verdant valley, trotting from cellar door to cellar door, to pass judgement on their wares, is a morning well spent and I thoroughly recommend it. At the amusingly named Ten Minutes by Tractor (the tractor is parked outside) the Pinots are again a revelation, outgunning the burly Shirazs. What do I know, though? I’m pissed on a horse.

Designed by local architects Wood Marsh, Port Phillip looks like a Bond villains first entry into wine making. A striking blade of concrete and glass, slicing a hill-top over looking the Western Port Bay, the estate is home to the Kooyong and Port Phillip Estate brands. Chef Simon Wests menu is inspired by the seasons and local produce. Heard it before? Sod it, the foods delicious, the view is breath-taking and I’m still merry from my equine booze breakfast. Yet again, this aspirational destination is owned by an emigre who is essentially an electrical engineer! What are they paying these people? I begin to think I live in the wrong hemisphere.

After taking the waters at the Peninsular Hot Springs a Japanese-inspired natural spa, filled with Zen-like calm and some very hairy people (alright, I was one of them), we head back for one final dinner. A big one. Having got us into some of the citys in demand eateries (including aforementioned tapas hot spot, Movida) our earthy hostess, Tourism Victorias Samantha Caffin, tops it with a degustation at Vue de Monde. A restaurant any city would be proud of, they treat us to a playful gastronomic display, including an amuse bouche muesli bar, celery sorbet, elderflower granite with frozen lime and Blackmore wagyu, with potato and nettles. Paired with some great Victorian wines, the meal puts us in such a good mood, I attempt a refrain from a bawdy sea shanty.

Apparently, I still have a lot to learn.

What I did learn was that through its strident determination to be considered a world apart from the preconceptions of Australian brazen shininess and posturing shallow effect, Melbourne and its environs offers a view of a mature and civilised New World. They’ve taken the best of old Europe, but refuse to give into self-conscious analysis or doubt. So not much to feel inferior about.

Their slogan could be Melbourne – if you don’t care for us, please do refrain from any beastly comments and retreat somewhere else to self-fornicate. See? Classy.

Whilst in Australia, Robert was shown Melbourne shopping with Hidden Secrets Tours (hiddensecretstours.com) blended wine at the Dominique Portet vineyard (dominiqueportet.com) and was also hosted by Yering Gorge Cottages (yeringcottages.com.au) and Quest Apartments (questapartments.com.au).