Sydney is like the pretty, popular girl in high school who from afar some people think a ditz, but who is in fact sharp, intelligent and can handle herself just fine when you meet her.

In short, she’s an object of both envy and derision depending on one’s perspective. Clearly many people around the world are envious – as the expat population of the city is roughly 30%. Speaking with some people we met, there’s a joke that with all the expats in the city, Sydney has just become England with good weather.

But not everyone thinks so. Many residents of Melbourne are happy to take the other tact: citing its high costs, corporate cleanliness, and its “too pretty” look as reasons not to live there: which, given real estate costs in Sydney is already something only a rare few can afford.

However, Sydney didn’t arrive on the scene, out of the blue, as some bombshell ingenue who swept up her winning tiara after being incapable of having an unscripted thought after forgetting her script: “Like such as ….the Iraq…”

The city came into its own from its own hard work, from what has to be the most unprivileged upbringing one can imagine: it was a penal colony.

Botany Bay (now home to the Sydney airport) was first discovered in 1770 by James Cook. 18 years later England started ferrying its criminals to Australia – a criminal sentence that was labelled “transportation”. The First Fleet, as it was known, arrived in 1788 to discover that Botany Bay may not have been the greatest spot to start things off, so they sailed just a bit farther North to what was known as Port Jackson, but now Sydney Harbour.

There it started where convicts tilled the land under some cruel wardens, while others were more merciful – until many were able to earn their freedom – then some land, and then became businessmen. Transportation ended in 1840 – at which time there was a viable settlement, doing well on its terms thanks to prisoners who, upon their release, had started businesses. In 1842, Sydney became Australia’s first city.

10 years later: GOLD!

There was a huge gold rush that nearly emptied the settlements, as the majority of people ran inland to get rich. It was a good risk for many: as they returned with their own private fortune. All this boded well for more development, and by 1901 Sydney was inaugurated into the Commonwealth, and had a population of 481,000.

Canadian content fact: Sydney got its name from Thomas Townsend who was credited with promoting the settlement at Port Jackson. Similarly, Sydney Nova Scotia was named after him as well – though for more ceremonial reasons, since Canada didn’t emerge from a penal colony, though its citizens might argue that during some winters it feels like one.

As Rose and I arrived in the city, one thing became abundantly clear: our backpacking budget wouldn’t stand a chance. Things were really riche – but we did our best. First off we found a “Free” walking tour of the city, which gave us an understanding of Sydney’s layout, taking us through the business district, around the edge of the harbour.

I say “Free”, because while there was no upfront fee, it was based on a tip you decided at the end of the walk. Some people didn’t wait that long, and bolted off without giving the guide a few bucks, which I thought was pretty crappy. Regardless, it was a decent way to get a sense of things, particularly the big icon of the city, the one that everyone brings to mind when they think of Sydney:

Much like Sydney itself, I learned that the Opera House had its own history of hardship and tribulation. It all started in 1957, when the city of Sydney awarded Danish architect – Jorn Utzon – the winning design after they had put out the project to tender.

Construction started in 1959 and it was projected to be finished in 1963. While things never go exactly to plan, their plan was a kite in a hurricane. The material for the fans on the exterior of the Opera house were redrawn and re-engineered during a four year period, eventually being solved in 1963. Costs climbed, suppliers were lost, political parties changed and patience waned.

In 1966, Jorn Utzon resigned, saying the political leader of the day – Minister of Public Works, Davis Hughes was an intractable M’fer in his dealings and had essentially bullied him into a position where he thought the only sane thing to do was leave.

When all was said and done, it was 1973 – 10 years later than expected and 14 times the budget. Utzon wasn’t invited to the opening ceremony and his name was left unmentioned during the pomp.

Slowly, however, as the years passed, and Utzon went on to complete other architectural projects around the world, the political climate softened and he was invited to draw up the design principles for the Opera House. This would give other designers an understanding of how to do fixes or add things in the future if projects were to come up.

Soon after he was awarded the highest architectural award in the world for his body of work. A year later an interior room was named after him at the Opera House, which then brought him closer in to the fold, such that he designed an addition to the Opera House with his son – called the Colonnade.

His public redemption was complete, when in 2006, the Queen who in 1973 hadn’t said jack about him, now gushed praise on him for his lifetime of work in her speech at the opening ceremony for The Colonnade.

Publicly, he was back in the good books. Something for which, in private, it seemed he was never in doubt.

Anyhow, all is iconic on the outside of the Opera House. But what of the inside?

Rose and I decided to find out – getting tickets for the super high brow event of listening to the Sydney orchestra play Sci-fi anthems for a couple of hours.

Star Wars, Lost in Space, Star Trek: there was a lot of material. And it was a lot of fun.

The rest of our time we spent at beaches in and around Sydney. First off, Manly beach – so named apparently from the Capt of the first fleet who, seeing the aborigines who lived there, found them masculine lads.

We toured around there, and to highlight how small our budget was in face of Sydney prices, this was lunch:

Afterwards, we went to the most popular beach in Sydney, Bondi:

There happened to be a kite festival going on, which was pretty neat, and we hung around there as long as we could, because loitering, thankfully, was free:

– until eventually heading back to our budget living in the city.

All in all, I thought Sydney was really pretty. But, not to be outdone, and to be fair and balanced, our next stop was Melbourne. There we’d get a glimpse of Australia’s second biggest city, plus go for a drive down the Great Ocean Road to see some tree bears.

Talk soon