Like every normal, red-blooded American kid growing up in the ‘80s, I hated history. (Sorry, Mrs. Beaver, but I think you knew this.) As I’ve gotten older, I’ve developed more of an appreciation for the subject, though the abomination that is The History Channel has nearly crushed it out of me. Dan Carlin’s Hardcore History is a much better way for me to catch up on what I blew off in high school. And of course, this newfound lifestyle of travel around the world has me wondering “just what exactly happened here?” every time we wind up in a new city.

Arriving in Sydney, Australia was no different. What I knew of the country came from Men At Work lyrics, a borderline obsession over Olivia Newton John in my teens, and that it’s where iocane comes from. None of those are what you’d call reliable sources. So when Lily from Context Travel offered us a couple slots on their Convicts, Strumpets & The Plague tour of Sydney, we jumped on it!

We met our “tour guide” Mark at the Custom’s House on a Saturday morning. I put “tour guide” in ironic quotes because that label doesn’t do him justice. Yes, he led us on the tour. But he also happens to be a post-doc student of Australian history. He did his thesis work on the history of pubs in Sydney, for crying out loud! It was abundantly apparent we’d get along famously.

Mark started the tour with a heavy focus on the convicts sent to Sydney for crimes committed in the UK. Convicts were the labor force that lifted Sydney from the bush. I had always pictured this part of Australia's history as a sort of Escape From New York experience, where prisoners were stranded on the shore somewhere and left to their own devices. Not surprisingly, that was completely inaccurate. The prison colony was quite well organized (have you met the British?), but it wasn’t set up in a way we’d recognize as a prison. It was more of a giant work camp, lacking guards, razor wires or even walls to keep the convicts in check. There was no “prison” to speak of. Just a growing settlement of skilled-but-convicted-of-crime workers -- hammer swingers, ditch diggers, architects, accountants, etc -- living alongside government officials and administrators. All of them focused on a single goal: Building the colony that would become the country of Australia. Oh, and not getting killed by the native wildlife in the process. That last part was enough to keep most of the prisoners in line.

Though much of the original settlement and buildings haven’t stood the test of time, there are still plenty of nearly-hidden artifacts. A small house nestled between a park and the arts museum marks the original harbor waterline. Steps that look like they were hewn out of the rocks are the actual steps hewn out of an area called The Rocks (the founders weren’t all that poetic) almost 200 years ago. And a myriad of plaques and signage are subtly worked into various architectural features, giving visitors who care to look a glimpse of days past. Though you have to know where to look. Mark knew exactly where, and deftly led us through small doorways and almost-hidden passages to see a side of Sydney most tourists gloss over.

We spent a good deal of time overlooking and learning about the controversy surrounding the construction iconic Sydney Harbor Bridge and the Sydney Opera House. We explored an archeology dig from the glass floor of the Sydney Youth Hostel. We saw the city’s scars after plague-fearing officials razed one neighborhood but let another stand. We stood on a corner and saw three historical pubs with the exact same name, all within sight (and presumably stumbling distance) of one another. We experienced all off these things and many more on a leisurely three-hour guided walk around the harbor, leaving us with plenty of memories and a much better appreciation for the history of this great city. Thanks for the tour, Context Travel! And thank you, soon-to-be Dr. Mark!

Context Travel operates expert-led tours in over 30 cities all over the world. If you want a better understanding of the history of a city, book a spot on one of their (very) intimate expert-led tours. And do it early on your trip to get the full context of the city! (Did you see what I did there?)