First Impressions of Sydney

The girl in front of me on the flight to Sydney leans forward and taps the women in front of her… “Excuse me miss, I think my friend kicked her thong under your seat, can you check for us?”

My ears inevitably perked up, and I looked around to see if anyone else was as easily excited.

The woman reaches down and pulls the flip-flop from under her seat and hands it back to the girls.

Disappoint sinks in, as does the realization that I’ve arrived in Australia.

Despite the slight verbiage differential, this is my first English-speaking “Tourist 2 Townie” mission and the first time I’ve had local friends already on location. You take for granted how  important this is when arriving in a new place.

Thanks to these factors, I was able to hit the ground running!

Sydney Skyline

I made it a point to arrive while there was still some summer left, and I’m so happy I did.

After only two weeks in town, it’s safe to say that Sydney is quickly becoming one of my favorite cities in the world.

I know it’s a bold statement, but to me there’s nothing better than a big metropolis combined with a seaside lifestyle (i.e. Rio, Istanbul, Barcelona, Chicago in the summer).

By American standards, Sydney is like a mix between San Francisco and San Diego. It has a strong Asian influence (really good food), a great surf culture and an abundance of green space. On top of that, it’s clean, safe and super friendly.

Parsley Bay in Sydney, Australia

As for intro activities, I explored the beaches, attended the Australia Open of Surfing, went to my first Aussie Rugby match, watched a movie in the park, and marched in the famously gay Mardi Gras parade. Here are a few pics…

Manly Beach Sydney Australia

Cool customer with the best view of Manly Beach and the 2016 Australia Open of Surfing.

Waratahs Super Rugby in Sydney

The dark and dramatic sky over my first Super Rugby match between the hometown Waratahs and the Queensland Reds. The crowd was a lot quieter than at an American Football game, especially for this rival match-up, but it was great to learn the rules and customs from local friends.

Moonlight Cinema, Centennial Park Sydney

The city of Sydney does an amazing job of putting on events and festivals throughout the summer, and one of the coolest is the Moonlight Cinema in Centennial Park. You can bring in your own food and drinks and rent bean bags right there.

Mardi Gras in Sydney Australia

Mardi Gras in Sydney might be one of the craziest things I’ve ever done. It’s a giant parade through downtown Sydney in celebration of all types of love! I had the opportunity to dress up and parade with the GLAAD organization in front of thousands and thousands of spectators.

Stay tuned for the first episode of “Travel Deeper Australia” where I’ll share more visuals and tell this wild story and in much greater detail.


If my first few weeks in Sydney is any indication of how this trip will pan out, than I’m in for a great few months ahead!

In the meantime, I’m kind of addicted to SnapChat at the moment, so if you want to follow along -> @GarethChat

My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


  1. We loved Sydney, definitely one of our favourite cities so far. We were there for Australia Day and had a lovely picnic in the park that ended with fireworks over the Opera House. Amazing!

    The final days of our Australian adventure will be spent there as well in a few weeks. Hope to be able to catch a rugby match, looks like fun!

  2. I have the same feelings you have about big metropolis and a seaside lifestyle. I live in Rio and I could not think of living in another place if it is not this kind of mix.

  3. My brother lives in Sydney 🙂 Although they just recently moved back from London and struggled to settled back into the city here! Nice start to your trip in Australia, have an awesome time here!! (From a fellow Aussie and travel blogger!! 🙂

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