Footpaths and Friendships: Finding the Heart of Sydney
Sydney is a fun city to visit. It’s more diverse than I realized at first glance. When I first imagined visiting, I pictured the Opera House, kangaroos, and maybe a few sharks. However, after conducting some research, it became clear that we didn’t have nearly enough time on this trip to accomplish everything we wanted to in this beautiful part of Australia.
The first thing we decided to do was to leave Sydney. I wrote about that portion of the trip in my previous article, which you can read here if you haven’t already. In this post, I’m going to tell you about the fun we had in Sydney itself.
Coogee: A Local’s Beach with a Laid-Back Beat
After returning our rental car to Simba Car Rental near the airport in the Mascot District (no, we did not want to drive in the busy metropolis of Sydney), we grabbed an Uber and checked in at the Crowne Plaza in Coogee.
Coogee is in the southeast part of Sydney. The hotel is located directly across the street from the beach and one street over from Coogee Bay Road, the main thoroughfare. There are a few boutique hotels, numerous restaurants, shops, a large cricket stadium, apartments, homes, and of course, the beach. It’s a great area.
Coogee Beach itself is lovely, featuring the Coogee Beach Rainbow Walkway and the beginning of the Bondi to Coogee Walk, an oceanfront footpath winding between cliffs and beaches. That walk was our plan for the following day. But first, dinner.
After settling into our room, we wandered over to Coogee Bay Road to check out our options. We could’ve checked online, but it was much more enjoyable to walk, people-watch, and soak in the smells coming from all the restaurants.
We landed at the Coogee Wine Room – Restaurant & Bar. The kitchen was winding down, so our only option was pizza, which was just fine by us. Pizza and a bottle of wine were exactly what we needed to kick off the beach portion of our trip.
Beach Scenes and Parallel Parking: Coogee Comes Alive
The pizza was delicious, and the wine was tasty. We took our time eating and watching the street scene unfold. This part of town is where Aussies come for their holiday, and there were plenty of college-aged folks enjoying their summer.
One of our favorite moments came when three young women drove up and realized they’d have to parallel park on a busy street. They stopped right in the middle of traffic, debating who could handle the task. Once they decided, a game of “race around the car” ensued to get the right driver into position.
This caught the attention of everyone nearby, including a group of young men across the street—tall, blond, and unmistakably Aussie.
As the young woman attempted to park, the crowd began calling out instructions:
“Move forward more.”
“Cut in!”
“Sharper turn!”
She didn’t make it.
Time to try again.
And again. And again.
She was getting embarrassed and exasperated. Her friends in the backseat were sinking lower and lower. That’s when one of the young men jogged across the street to the car. He crouched down at the driver’s window and, like a big brother, politely offered to help. She gratefully accepted. He hopped in and, with a couple of perfectly timed turns of the wheel, the car was parked.
The crowd erupted in applause. Everyone piled out of the car. The young women offered heartfelt thanks (and a few giggles) and went on their way. Our hero returned to his friends, who greeted him with cheers and a beer.
It’s always a delight to witness spontaneous kindness and good humor in the wild.
Footpaths, Tide Pools, and a Parade of Birds
The next morning, we had a healthy breakfast before starting the Coogee Beach and cliffside walk. We began at Giles Baths, a natural bath area resembling large tide pools for humans. A few people were swimming, but what caught our eye were the birds in the nearby grassy area, our first up-close sighting of the Australian Ibis.
The Whaldo’s enjoying the beautiful Coogee to Bondi Coastal Walk / Photo by Whaldo Digital Content
As it turned out, we were about to have a rich birding experience, but we didn’t realize it yet. The path was full of discovery. We passed cliffs, parks, memorials, diving clubs, lawn bowling clubs, and swimming clubs. We wandered through Gordons Bay, Clovelly Beach, Waverley Cemetery, Bronte Beach, Tamarama Beach, and finally ended at South Bondi Beach.
What should have taken around three hours took us nearly five, thanks to all the birds, scenic lookouts, and beachgoers. When we reached North Bondi, we stopped at North Bondi Fish and grabbed a patio table overlooking the water for a cold beer and a snack.
Bondi Beach Vibes and the Dive Bar of Our Dreams
As the sun dipped lower, we strolled along the Bondi Promenade and cut over to Campbell Parade to find a spot to relax before heading back to Coogee. There were plenty of places to choose from, but, true to form, we found the best dive bar and joined in the revelry. Chuck Trailer’s Bondi Beach was exactly the kind of spot we love.
It felt like home, like being back in San Diego’s Mission or Ocean Beach. Laid-back, beachwear-friendly, and full of good energy.
The best part? The spinning wheel.
The cardboard roulette-style wheel had numerous “prizes”, with highlights including a free drink, food discounts, a time-out, and a shoe drink. Most wanted to land on the free drink, and we did see that happen.
We witnessed a time-out, which means the bartender banishes you from your group and you have to leave the premises (since it’s all outdoors, you simply walk through the gate). You then have to watch your friends have fun without you for 15 minutes. Once your time is up, the bartender calls you back in, and you rejoin your crew, who have been teasing you and taunting you the entire time.
The funniest was a shoe drink, though. We saw that happen three times. Once you land on that, you must remove your shoe; the bartender pours a drink into it, and then you drink it. If you are wearing sandals or similar footwear, you are not immune to this punishment. You can borrow one from your friend, or there is a spare shoe just for this occasion.
A highlight of the night was when we watched a group of four young businessmen come in, and the staff persuaded the top-dressed one to spin the wheel. You guessed it, he landed on the shoe. He had some very nice dress shoes on, yet, in good spirit, he met the challenge head-on, which caused a massive uproar from the crowd and a whole shift in attitude among his friends. They went from business to casual in less than 30 seconds.
Fun stickers from Chuck Trailer’s / Photo by Whaldo Digital Content
Trivia, Toasts, and the Unexpected Joys of Coogee Nights
After a warm sendoff from the staff (plus some cool stickers), we Ubered back to our hotel. Still hungry, we wandered back to Coogee Bay Road and ended up at the sports bar inside the Coogee Bay Hotel. It was crowded, but we found a table, ordered a quick bite, and expected a low-key evening.
Then, team trivia began.
That explained the crowd. Although we’re trivia fans (our team name is “We Suck at Trivia”), we didn’t join in, just enjoyed the show. The host was funny, the energy was great, and it turned into another unexpectedly fun night. We stayed longer than planned again, cheering along as the game ended in a three-way tiebreaker.
We strolled back to the hotel in the cool ocean breeze, ready for a good night’s sleep.
The Rocks and Circular Quay: Big Views and Easy Days
The next day, we relocated to the Rocks district. We checked into the Park Hyatt Sydney, ideally situated between the Sydney Harbor Bridge and the Circular Quay, with views of the Opera House directly across the water.
The location was ideal for the next few days. Circular Quay is the central hub for ferries and light rail, so our next few days were easy to plan: walk the bridge, ride ferries, visit the Opera House, explore Darling Harbor, and take in a few museums.
After unpacking, we walked across the Sydney Harbor Bridge and back again, soaking up the views and snapping photos of the Opera House. We then headed to the Quay, purchased our transit passes, and jumped on the light rail.
Our first stop was Paddy’s Haymarket, followed by a stroll through Chinatown. It was the Year of the Dragon, and we were there to ring it in. We walked all afternoon and throughout the night, never hopping back on the light rail or bus. We finally made it back to our hotel late, happy and tired.
From Botanic Gardens to Opera House Marvels
The next morning, we explored the Art Gallery of New South Wales, then walked the entire Royal Botanic Garden, encountering a wide variety of flora, fauna, birds, and even a few spiders (which, oddly, I always enjoy spotting). We visited the many monuments scattered throughout the Garden, and the paths ultimately led us straight to the Opera House.
We wandered around the outside and eventually joined a group entering the building. We didn’t know where they were going, but we wanted to check out the interior of the Opera House. Most of the group headed into one of the theaters, and we noticed they had tickets, so we gave that one a pass (who knew there were multiple theaters in there?). We ambled around, exploring the rest of the place on our own.
From there, we walked to Darling Harbour, an area filled with restaurants, shops, the Sea Life Sydney Aquarium, and more. We spent the rest of the day and night wandering from place to place, listening to live music and stopping for food and drinks along the way, until it was finally time to call it a night and head back to the hotel. Happy and exhausted.
Manly Ferry Magic and a Feast of Friendships
On our final day in Sydney, we took the ferry from Circular Quay to Manly. Our dear friend Ms. Rhonda, whom we’d visited earlier in Orange, grew up in Manly and gave us very specific instructions on where to get the best fish and chips.
Onboard, my charming husband struck up a conversation with a group of women wearing matching wine glass earrings. One wore a brooch instead—she didn’t have pierced ears.
This lovely group of ladies had created a women’s luncheon group. Once a month, they all meet at Circular Quay and catch a ferry somewhere for a lunch and wine date with each other. They all took turns introducing themselves and explaining their outing.
Throughout the ferry ride, we learned that they seize the opportunity to dress up, apply their makeup, don their jewelry, get out of the house, and socialize with each other while enjoying good food and wine. Today, they were going to a lovely spot in Manly, the Hotel Steyne.
They were delightful, warm, welcoming, and full of life. It was a joyful ride across the bay.
Once in Manly, my husband and I walked hand in hand along East Manly Cove Beach. It was shady and peaceful. We passed the Yacht Club and ended up at the Manly 16ft Skiff Sailing Club restaurant.
We then decided to head back towards the ferry wharf so that we could have lunch. However, on the way back, we walked along the residential side of the park to admire the pretty houses with their perfectly manicured yards, vibrant with a variety of plants and flowers. The street was postcard worthy.
Following Ms. Rhonda’s directions, we found The Corso, walked toward the beach, and looked for a blue-and-white sign. We found it, Manly Ocean Foods, a takeaway joint with a long but fast-moving line and the irresistible smell of fried seafood.
We ordered, grabbed our food, and sat on the boardwalk across from the beach. It was exactly as she had described, and the food was delicious.
Laughter, Legends, and One Last Pint in Manly
Afterward, we wandered back along the restaurant-lined street. That’s when we spotted a big restaurant with sidewalk tables and decided to stop for a pint. We found a table right along the sidewalk across the street from the beach and relaxed in the afternoon sun, soaking in the fun beach vibes.
When I went inside in search of the bathroom, I saw just how big the place actually was. The bathrooms were tucked away, as usual, and as I was walking back, I heard familiar laughter. I turned to find a large table with all of the lovely luncheon ladies. Just as I noticed them, they saw me, and they all erupted at once, greeting me happily.
Some inquired about how we had spent our day, and after a brief chat, I left their smiling faces as they jumped back into their easy conversations with each other. It was then that I realized we were at Hotel Steyne.
We lingered there, people-watching and imagining Ms. Rhonda growing up in this charming town. Now we understood why she wanted us to visit.
The luncheon ladies passed by our table on their way out and wished us well, still chatting and laughing as they headed toward the wharf. We soon followed, ferrying back to Circular Quay as clouds gathered and the air cooled. We grabbed our hoodies and walked the Sydney Harbour Bridge one last time to take in the city’s lights.
Flying Foxes at Dusk: Sydney’s Perfect Sendoff
The next day, we were scheduled to board a cruise ship and sail to Melbourne, then Tasmania, before continuing around New Zealand. We were looking forward to this next leg of the adventure, but wanted to close out our time in Sydney with one last evening in The Rocks District.
We sat outside at the Fortune of War, the city’s oldest pub, enjoying a drink and reviewing our plans for the next day, when we heard a rising raucous.
My husband and I figured it must be a flock of something coming in to roost in the park across the street as the sun was setting. We kept our eyes on the sky, the noise growing louder and louder, until suddenly, they appeared.
Hundreds of flying foxes.
Australia’s largest fruit bats, the Grey-Headed Flying Foxes, burst from the park and into the night sky. Their wingspans can reach three feet, and the sound they make as they take off is something you never forget.
It was the perfect sendoff.
We loved Sydney and the adventures beyond it. With full hearts and a touch of wistfulness, we turned toward the next leg of our trip down under, grateful for all we’d already seen and excited for what was still to come.
- J.S. Whaldo
Practical Travel Notes
If you’re heading to Sydney in late January, keep a few practical things in mind:
First, the sun is no joke. The UV rays in Australia are powerful, even on cloudy days. You’ll want sunscreen, a wide-brimmed hat, and sunglasses as your constant companions. We reapplied sunscreen multiple times a day. Don’t underestimate that sun.
Although it’s the height of summer, January can bring occasional showers and cool evenings, especially near the water. Pack a light rain jacket and something warm for nights out; layers are your friend.
Where we stayed:
Crowne Plaza Coogee Beach – A relaxed, oceanfront hotel just steps from the sand. It’s easy to settle into a beach rhythm here before diving into the energy of the city. (NOTE: The hotel is currently closed as they undergo a major transformation, reopening as InterContinental Sydney Coogee Beach from November 2025.)
Park Hyatt Sydney – Perfectly situated on the harbor with breathtaking views of the Opera House. A luxurious base for exploring Sydney’s historic and cultural sights. (Use your points! What are you saving them for?)
Where we ate:
Coogee Wine Room – Restaurant & Bar – A cozy, stylish spot where we lingered over pizza and wine while watching the street come alive. (Your dinner show might include some hilarious parallel parking attempts.)
Chuck Trailer’s Bondi Beach – Fun and funky with great beachside energy. Burgers, wings, beer, and views. What more do you need?
Paddy’s Haymarket – Come for the market browsing, stay for the fresh snacks and easy eats. A great place to graze.
Manly Ocean Foods – Classic fish and chips by the beach. Grab a seat outside if you can and watch the world go by.
Things to do:
Walk the Sydney Harbor Bridge – The views alone are worth it, and you’ll feel like you’re in the heart of it all. (You can climb it too!)
Explore The Rocks – This historic district is full of cobblestone lanes, shops, markets, and stories from the city’s early days.
Take the ferry to Manly – The ferry ride offers incredible harbor views, and the beach town on the other side is well worth exploring.
Coogee to Bondi coastal walk – A breathtaking path with sweeping ocean views, rocky cliffs, and spots to stop along the way.
Evening walks through the city parks – Don’t be surprised if you look up and see giant flying foxes soaring overhead at dusk.
Royal Botanic Garden - Botanic Gardens of Sydney encompasses three world-leading botanic gardens, Australia’s premier botanical research institute, and Sydney’s leading outdoor activation precinct.
