As soon as I checked into my apartment in Bondi Beach, Australia, I sent an email to a few local Instagramers. It felt strange, as though I was a fangirl reaching out to local celebrities. Usually I’d meet locals randomly in person, just by striking up a conversation. But many of the travelers on the Passport Express crew had had great success meeting people through Instagram. Jeffrey Gerson had offered me a list of people to contact in Sydney, and I figured I’d give it a shot.

That list changed my entire experience. Tim DeNoodle immediately responded with an offer to get coffee the next morning. We met up at a cafe where he shoots many of his popular shots, Bondi Icebergs. The Icebergs is an ocean pool along the cliffs at the start of the two-hour coastal walk from Bondi to Coogee. The walk passes five of the area’s most iconic beaches.

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The pools are one of the most photographed spots in Bondi, and the cafe gave us a perfect view of the pools and the beach that lay beyond. The best day to swim at Icebergs, he told me, is Friday, just after they’ve cleaned the pools. They’re fine anytime, he added, but best on Fridays. Another favorite bath of his is Wylie’s Baths, at the far end of the coastal walk, in Coogee.

Just chatting with Tim for that half hour over coffee made me realize that I was sitting across from a man who knew more about Bondi and the surrounds than anything I’d find in a travel guide. Before I knew it, we’d made plans to spend the next day touring his favorite local haunts. It also turned into a bit of a tour through history.

Tim first arrived in Bondi in his late teens, a Sydney kid moving to a fairly rundown beachside town that was “not at all what it is today,” he says. Hippies and people seeking alternative lifestyles ran the show throughout the 1980s. Where there are now organized murals painted along the walls behind the beach, there was once legitimate graffiti. The coffee shops and posh boutiques only moved in over the last five to 10 years, he adds. You can sense how personal Bondi was until recently, even just in the names of the restaurants. The oldest ones are simply the owners’ first names: Seans, Jed’s, Gertrude and Alice.

As we started to drive towards a few harbor viewpoints slightly north of town, we passed Seans. “It’s spectacular, genuine,” he said. Everything is sourced from the owner’s own farm. The restaurant opened in 1993, predating the famous Icebergs. Glancing through the windows as we pass, I can see that looks comforting, somewhere I’d love to spend a night with friends gathered around the large tables.

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We also passed Porch and Parlor, where it feels like you’re sitting on a friend’s porch, looking out at the water. I’d later enjoy fresh breakfast bowls overflowing with quinoa, greens, and poached eggs while sitting at the counter at Porch’s massive windows.

Continuing on Military Road north of the city, we passed a few spots with sweeping views of the Sydney Harbor, where I caught my first glimpses of the Opera House and Harbor Bridge. We stopped briefly to see Watson’s Bay, where people were already gathering at a microbrewery at noon. Who could blame them – the weather was scorching.

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We then continued down Old South Head Road, parked the car, and went for a long stroll along the cliffs of South Head, part of Sydney Harbor National Park. The sidewalk path took us by a nude beach and an historic lighthouse. Tim explained that South Head and North Head form the opening to Sydney Harbor, and offered a few history lessons on all that happened here during the World Wars.

We passed a quaint community bay on our way in and out. Sydney Harbor is lined with these inlet bays – and our next stop was one of the most secluded of them all.

Tim pulled the car into a nondescript neighborhood and parked along what looked like any other residential street. The number of cars parked there gave away that something was nearby. Walking down a sidewalk – there were no signs – soon revealed the hidden gem: Parsley Bay, a large U-shaped inlet protected by a shark net. Kids were jumping off a small dock near the widest part. Farther back three teenage boys were swinging off a rope strung from the top of a steel footbridge. A few teen girls were jumping off the bridge; little kids were playing with buckets on the beach. It was the picture of summer. We dropped our bags and jumped in the clear blue water.

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Our local adventure eventually had to end, but not before dropping me at one last favorite: Jed’s. The interior walls of this cafe are lined with Jed’s surfboards. The exterior walls are all paneled windows that swing open, allowing sunlight to pour in. The staff was as friendly as they come and the hearty skillet scramble was exactly what I needed after a day of swimming and sunshine with the  best tour guide around. And to think, it all started with Instagram and an email to a virtual stranger.

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