Arriving not only in a new country, but in a new city at 6am is both exhausting and exhilarating. It means you’ve survived the dreaded redeye flight and have an entire day ahead of you to explore your new surroundings.
For my family and I, that meant that I booked us on not one, but two tours, to get us acquainted with the first city on our whirlwind tour of Australia. Little bro was incredibly excited, but mom… not so much! *laughs*
Before we’d left, I’d taken a look at the different tours available in Sydney, and I came across the “I’m Free!” tour company. It reminded me distinctly of the Sandeman’s tours Matt and I had frequented while we were in Germany, so I was pretty excited. Essentially the way the tours work is that you don’t pay a flat registration fee for your tour. Instead, you attend the entire tour and at the end, you pay what you believe it was worth. The ideology behind this style of tour is twofold: First, it’s so that tours can be affordable to the masses, so everyone from students to the elite are able to learn about and appreciate the city and all it has to offer. Second, from what all of the tour guides have explained to us, it encourages them to always give “their best” tour, because each and every time they lead a tour, the attendees are evaluating how enjoyable it is, and then compensating them 
accordingly. I actually think it’s a really interesting way to run the tours and Matt and I have had some *incredible* experiences with free tours.
So, I reserved spaces for us on the I’m Free City tour and also The Rocks evening tour!
We attended the 2:30pm Sydney Sights tour, and it was absolutely excellent. It truly did run for approximately 3 hours, and we were lucky enough to have the company founder lead our tour! As Americans, we don’t receive a lot of Australian history through the course of our education, so I felt like we had a complete crash course with the I’m Free! Sydney Sights tour. Not only were we taught about basic Australian history, but we were also shown some of the most unique and interesting parts of Sydney as well. The city is such an amalgamation of new and old, historic and modern, that we were mind blown. Around one corner was the Rum Hospital, where we got to hear the medical history of 
Sydney and how illicit activities in the history of the city have lead to its progress and growth. And yet, around the next corner, our tour guide was ushering us into an alleyway and showing off some of the modern art installations done in the city. It was a complete whirlwind tour, and we loved every second of it. Even mom, who at the end we dragged up 2 flights of stairs to check out the view across the Harbor and of the Sydney Harbor Bridge. I think she hated us a little bit in that moment, but it was just such a sunny and beautiful day, we couldn’t let her miss the opportunity!
However, after we dragged her around for 3 hours, mom was pooped out and decided to head back to the hotel instead of attending The Rocks tour with Matt and I. We accepted her exhaustion, but we did traipse around for a snack with her before letting her head off.
The Rocks tour met at one of the locations we had walked past on the I’m Free! tour, which was perfect for us, since it was our first day in the city and we didn’t know how to get anywhere we hadn’t been before… hah!
I’m SO glad we did the second tour though! We got a completely different feel for the city in the evening, hearing tons more in depth details about the history of the illegal trading and “darker” sides of the city, especially during its formative years. You’ve got to imagine that a city that was founded by sending over convicts had problems, and you wouldn’t be wrong about that!
The Rocks tour walked us around some similar areas to the Sydney Sights tour, but primarily different sights and completely different stories. It was a great compliment to the afternoon tour, and for a relatively fit individual, a completely doable first day in the city! If you’ve never been to Sydney before and you have *no* idea where to begin, I’d highly recommend the I’m Free! tour series for your first or second day. Not only were the tours excellent, but our guide (we had the same one for both tours, which was wonderful since we loved her!) had plenty of anecdotes and a plethora of recommendations for the rest of our stay! We’re definitely going to check out the harbor restaurant with $15 steak & chips overlooking the operahouse and umm… the hidden bar scene?! Who knew! I’m sure we’ll be hitting some of those while we’re here so stay tuned!
