What do you get when you mix three days, endless sunshine, and the buzz of a harbor city that never sleeps? One unforgettable adventure.
- Chach Kelly
- Jun 1
- 9 min read
Welcome to Sydney.

We don’t need to oversell it—it’s already one of the world’s most iconic destinations. But if you’ve got a long weekend and want to make every moment count, here’s how to do it right.
With its perfect mix of legendary landmarks, jaw-dropping natural beauty, buzzing culture, and a laid-back vibe, Sydney suits every kind of escape. Whether you're chasing cocktails and rooftop bars with the girls, planning a romantic weekend away, or looking for a fun-filled family getaway—this city delivers.
Getting into the city is refreshingly simple. Sydney’s public transport is surprisingly efficient—especially from the airport. Skip the Uber and head straight down the escalators to the train platform. In just 15 minutes and for only $15.40, you'll be in the city center, no Opal card needed—just tap on with your bank card. It’s fast, easy, and kind to your purse straps.
Yes, there are plenty of flights in and out of Sydney every day, but if you're smart (and we assume you are), you'll book the first flight in. The plan? Drop your bags at the hotel and dive right into a weekend of sights, scenery, food, and serious relaxation.
Day 1: Ferries, Coastal Views & A Whole Lot of Walking (Sorry, Not Sorry)
We really wanted to make every second count this weekend, and were lucky enough to get away Friday to Sunday. After dropping our bags off at the great-value Amora Jamison Hotel—tucked just off George Street—and grabbing a quick coffee at Georgie Boy’s, we walked the 10 minutes to Circular Quay to catch the ferry to Rose Bay.
Starting the morning on the water, heading away from the crowds, was the perfect way to ease into the trip. Cruising past the Harbour Bridge and Opera House on a clear, sunny morning? Honestly, pinch-me levels of perfect.
Rose Bay is one of those hidden gems that has a hint of luxury without the attitude. We fueled up at Collins Beach Café (get the breakfast burrito—thank me later), and made a quick stop at LaVie & Belle to grab a sweet treat for later.
And then... the walking began. Much to my husband’s dismay (he "doesn't understand my obsession with walking everywhere"), we set off toward Shark Beach. But here's the thing—when you walk, you discover things you’d never see from a bus or car. The walk offered stunning glimpses of the harbour in every shade of blue, and little peeks of the city skyline along the way.
From Shark Beach, we continued up to South Head and Hornby Lighthouse—easily one of the best spots to look back across the harbour. A great place to stop for a snack and take it all in.
Now, me being the golden retriever-energy walker that I am, we pushed even further south, sticking as close to the coastline as possible: Gap Bluff Lookout, Macquarie Lighthouse, Vaucluse Viewpoint, Diamond Bay Cliff Walk, all the way down to Ben Buckler Point in Bondi. With photo and snack stops, this whole section took us just over 4 hours.
If you’re more like my husband (i.e. allergic to walking), there are plenty of buses and rental bikes to get around faster.

Once in Bondi, I couldn’t pass up the chance to try Bennett Street Dairy after seeing it everywhere online. We went with the Reuben—no regrets—but whatever you do, get the cookie. Gooey, crumbly, sweet perfection.
After soaking up the chaos of Bondi Beach (surprisingly small in real life, but still as hectic as you’d imagine from Bondi Rescue), we kicked off the Bondi to Coogee coastal walk. It’s one of those must-do experiences—six kilometers of stunning views, natural rock pools, and photo ops around every corner. Fair warning though: if you’re here between December and February, expect peak crowds.
By the time we arrived in Coogee—nearly two hours later—even I was ready for a beer. We grabbed a couple rounds at Coogee Pavilion (great vibe, not-so-great prices) before deciding to call it and head back to the hotel for a freshen up.
Showered and revived, we kicked off the night with pre-dinner cocktails at Dean & Nancy on 22. Sleek, sexy, and full of moody lighting and panoramic views—it feels like somewhere Carrie Bradshaw would sip a martini while waiting for the girls. Amazing service, and equally amazing cocktails.
Then it was off to dinner at the always-buzzing Mr. Wong. This place is a Sydney institution for a reason. Order the duck pancakes and whatever dim sum is on special. Don’t ask questions—just eat and thank me later. Your taste buds will be dancing.

Day 2: Sunrise, 10km of Views, and Pizza with the Youths
Early start—and so damn worth it.
We grabbed a 10-minute Uber while watching Friday night’s party animals stumble out of bars, which honestly made the whole "sunrise mission" feel even more justified. The kayak team was super friendly, knowledgeable, and patient (bless them).
Once we paddled around the corner and had the sunrise on our right, with the Opera House and Harbour Bridge on our left, it was a total "wow" moment. We chose a double kayak because, let’s be real—I’m a passenger princess. Even so, the waters were calm, the group wasn’t racing like Olympic athletes, and the pace was chill and enjoyable.
There were plenty of stops at scenic spots, and the guides helped us grab great photos. It’s honestly one of the most unique, peaceful, and memorable ways to see Sydney from a totally different perspective. After we got back to the marina, we headed next door for a coffee and pastry (included!) while the team sent around the photos from the morning. 10/10 morning well spent.

Time to Walk (Again, Sorry Husband)
Sydney has so much to do, and depending on the weekend you're chasing—cocktails, beaches, relaxation, food, or all of the above—you can tailor your experience easily. That said, Sydneysiders are outdoorsy. The weather helps, sure, but a lot of what Sydney offers is based around being out, about, and moving.
So yes... unfortunately for some (read: my husband), Day 2 meant more walking.
We were both surprised by how frequent and on-time Sydney buses are. A quick ride later and we were at The Spit, ready to kick off the Spit Bridge to Manly walk. It's one of the Northern Beaches’ most iconic walks—almost 10km (even more if you take little side adventures), and moderately challenging.
The views are unreal. The track is well-maintained, and it’s less crowded than Bondi to Coogee—arguably even more beautiful. There are a few uphill sections, but they’re short and absolutely worth it.
You’ll pass hidden little beaches perfect for a picnic or swim, Aboriginal engravings just off the boardwalk, and the stunning Crater Cove Lookout, which gives you panoramic views of the city, Watsons Bay, North and South Heads, and Manly.
As you approach Manly, the beaches get more and more picturesque—so take your time. Manly itself is bustling. It’s not the quietest spot, but for visitors, it’s full of life and mostly outdoor fun (I told you—these people love being outside).
Here’s what you can do:
Chill on the beach (or go full tourist and take a surf lesson)
Snorkel at Cabbage Tree Bay
Hire a kayak or paddleboard
In whale season (May–November), keep an eye on the horizon
We were keen to say we "did stuff" but also wanted to relax. Felons Brewing was the perfect in-between. There’s live music from Wednesday to Sunday, different seating areas depending on your mood, and a menu so varied you’ll definitely find something to love.
We had some oysters and a tasting paddle, then landed on their ginger beer as the winner. Honestly, same harbourside views as more expensive spots like Coogee Pavilion—but our bill was about two-thirds the price. Made us seriously wonder: is the view ever really worth that much?


After the oysters, we needed carbs. Enter: Pocket Pizza, Manly.
Yes, we were easily the oldest people there (mid-30s in a sea of 20-somethings), but once the food arrived, we stopped caring. Do yourself a favour:
Prosciutto focaccia
Burrata
The Lamborghini
Fusilli in vodka sauce
I could’ve eaten six of those pastas. We caught the ferry back around 9pm and honestly? It was a party. Sunset skyline, people singing, groups chatting—it was the perfect end to a very active but epic day.

Day 3: Markets, Massages & One Last Steak
Finally—a lie-in.
As much as I wanted to squeeze every moment out of the weekend, even I needed a little break. Now, I say "lie-in," but for us that meant 9am. Still early for some, I know. But hey, I can sleep when I’m dead, right?
We kicked off the morning with a casual stroll through Barangaroo Wharf—just to stretch the legs. After nearly 60,000 steps over the past two days, our bodies were definitely feeling it.
That’s when we stumbled across The Rocks Markets—completely unplanned, but such a win. If you're a market lover like me, it’s a dream. Local artwork, handmade jewellery, candles, artisan gifts... I even started mentally Christmas shopping. Yes, I know it’s early, but if I buy it now and forget about it until December, it's basically free. Girl math.
We sat on the grass and watched people do yoga. That’s not really our vibe—but good for them. Instead, we drank wine and sampled spirits at 10am—because it’s totally fine at a market. No judgment there. Our "breakfast" consisted of juice, paella, and Turkish doughnuts. Because we could.

Bellies full and shopping bags heavier (which, yes, my husband carried—he's a saint), we made our way to Endota Spa for a couples treatment. Absolute bliss. We both have demanding jobs, and this was the perfect way to unwind. Massages, facials, and a foot treatment—that was my husband’s reward for all the walking I "forced" on him.
Afterwards, we headed to JAM Record Bar for a cheeky afternoon wind-down. The vibe? Immaculate. Tiny box seats outside are perfect for people-watching, which I live for. With over 15,000 vinyl records, the music was unreal—think vintage soul, disco, and unexpected gems.
I stuck to JAM-aretto Sours all afternoon (when in Rome), soaking up those last golden hours before heading back to the hotel to freshen up. Even though we’d checked out, they stored our bags and had great facilities for a quick change.
Dinner was at 6HEAD, a gorgeous steakhouse tucked into a restored 1839 sandstone building. The interior? Old-world charm meets modern luxury. The wine list was elite—and bonus points for not just sticking to NSW wines. I even found a glass of my absolute favourite: Hentley Farm ‘The Beast’ 2016. (Expensive. Worth it. Adelaide blog coming soon.)
The steaks were phenomenal, as expected, but don’t skip the XO prawns. They’re everything.
The best part? Our hotel was just 10 minutes from the wharf and less than 5 minutes from the train. After dinner, it was a slow walk back, a quick train to the airport, and we were home in time for the last flight—happy, full, and already planning the next trip.

Of course depending on where your coming from or the vibes you want for your weekend there are so many things you can do. Other top recommendations that we have done on other visits:
Climb the Sydney Harbour Bridge – For unbeatable 360° views of the city and harbour.
Sydney Opera House Tour – Even if you don’t catch a show, the behind-the-scenes architecture tour is worth it.
Royal Botanic Garden Walk – An easy, lush stroll with stunning views of the Opera House and Harbour Bridge.
Watsons Bay + The Gap Lookout - Catch the ferry from Circular Quay, enjoy fish and chips at Doyle’s, and walk up to the cliffs for incredible ocean views.
Ku-ring-gai Chase National Park - About 45 mins from the city. Offers Aboriginal rock art, secluded beaches, and walking trails.
Swim in an Ocean Pool - Try Bronte Baths, Mahon Pool in Maroubra, or Fairy Bower near Manly.
West Head Lookout - Hidden gem with a view over Palm Beach, Pittwater, and Broken Bay. Feels like you’ve left Sydney.
Spice Alley - A hidden laneway of hawker-style Asian street food in Chippendale. Great for dinner under the fairy lights.
Paddington Reservoir Gardens - Underground Roman-bath-style garden built into a heritage site. Peaceful and photogenic.
Blue mountains - there will be another post on this.
Other Restaurants / Cafes / Bars That Are Totally Worth the Hype
Totti’s (Bondi or CBD) – Woodfired bread, burrata, pasta. The Bondi location is buzzy but beautiful.
Hubert – Underground French restaurant that feels like stepping into a Wes Anderson film.
Saint Peter – Sustainable seafood, innovative dishes. Truly one-of-a-kind in Australia.
Paramount Coffee Project – Funky interiors and excellent brunch options.
Single O (Surry Hills) – Specialty coffee pioneers.
Opera Bar – A classic, but iconic for good reason
If you're craving a weekend of adventure, sunshine, good food, and that perfect mix of activity and indulgence—Sydney delivers. You just need three days, a good pair of shoes, and maybe someone willing to carry your shopping bags.
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