City of Dreams – A Romantic Short Break in Sydney


Matthew Brace digs beneath the surface of Australia’s most buzzing metropolis to discover the romantic side to Sydney.

Sydney, Australia

The sun was high and the breeze was Pacific-fresh. We were surrounded by the lushness and tranquillity of the Botanic Gardens, while ahead of us lay the harbour, its diamond-encrusted waves dazzling in the sunlight.

We flopped onto the grass, popped the cork on a bottle of chilled champagne and prepared to devour a super-luxe picnic courtesy of the wonderful Sydney Picnic Company. It was packed with mozzarella and prosciutto, prawns with chilli and lime, slightly spicy Le Dauphin cheese, roasted tomatoes, candied sour cherries, freshly baked sourdough baguette and salted miso chocolate brownies. Heaven in a hamper.

Welcome to Sydney, where everything seems possible. Waking to see the sun kissing the Opera House’s scallop shells? Can do. Gourmet harbourside picnic? No problem. Strolling along one of the world’s most romantic coastal paths? Easy. Evening cocktails in a secret speakeasy? Sorted.

Full Harbour King Club Room at the Four Seasons

But where do visitors start in a city so naturally beautiful that even the simple act of catching a bus to the beach with a loved one can feel romantic? Sydneysiders rise with the sun and for visitors there’s probably no better spot to do that than a Full Harbour King Club Room at the Four Seasons. Rustle up a couple of ristrettos in your in-room Nespresso machine, hop back into the soft, cotton sheets and watch the flags fluttering from the great arc of the Harbour Bridge and the busy green-and-yellow ferries pirouetting as they come and go at Circular Quay.

You could stay in bed for your entire stay and still have a fabulous time, but there are lots of things to see and do out there.

The Boathouse, Shelly Beach

One of our favourite breakfast spots is the Paramount Coffee Project on Commonwealth Street in Surry Hills. It has a wide array of coffees and the crumbed eggs with mustard-braised ham hock and the soft baked eggs with habanero salsa are excellent. Another is over at Manly. Catch the Manly Ferry from Circular Quay and walk to The Boathouse on beautiful Shelly Beach for a smoked salmon fritter.

To help shed the carbs, catch a bus from Circular Quay to Bondi and walk the stunning coastal path past the beaches of Tamarama, Bronte, Clovelly and finally Coogee. In late October, this coastline is taken over by modern artworks as Sculpture By The Sea hits the town—well worth seeing.

There are loads of great walks around the harbour too. Head around South Head to see the both the harbour and the Pacific in the same panorama. Walk through bushland from Taronga Zoo to Balmoral Beach on the North Shore for city skyline vistas. Stroll around the Botanic Gardens for some of the best views of the Opera House and Harbour Bridge.

If you’re city slickers rather than beach bums, start your day at the Museum of Contemporary Art in The Rocks for a culture hit, and brunch if you fancy it at the excellent rooftop MCA Cafe. Then, head for the bridge. One of the things we always found romantic when we lived in Sydney was to climb the Bridge Stairs off Cumberland Street, walk across the bridge on the eastern footpath (Opera House side) to Milson’s Point, stopping frequently to drink in the view. Then, we’d wander through the narrow lanes to Kirribilli Wharf and catch a ferry back to Circular Quay. 

Sydney Picnic Company | Image: Matthew Brace

Kirribilli also has a terrific spot to have your gourmet picnic: Lady Gowrie Lookout, a secret pocket park with stellar harbour views. A gourmet picnic is something different, private and very romantic. The hard yards are done for you. All you have to do is pick your venue. Husband-and-wife team Simon and Natalie Thomas have been running the Sydney Picnic Company for more than a decade, creating epicurean hampers full of delicious and creative food for thousands of picnicking couples.

“We have a catering background, but we’re also die-hard romantics,” said Natalie, “so this was the perfect fit really.” Apart from the food, the couple is quite hands-off: “We provide the hamper, food and cutlery and the picnickers choose their spot and do the rest.” Quick tip: Sydney’s got much tougher on alcohol in public so keep the champers hidden and take a couple of reusable cups rather than champagne flutes.

If your heart is set on fine dining, Sydney is packed with some of the southern hemisphere’s best restaurants. Many book up way in advance while others are walk-in only, so it pays to plan ahead. Our culinary friends recommend sister restaurants Poly and Ester (get it?), as well as Alberto’s Lounge (Italian) and Firedoor where wood-fired ovens, grills and a hearth replace gas and electricity. For seafood, St Peter is a favourite and full of surprises: where else would you find a stinging nettle, egg yolk and smoked yellowfin tuna ham pie?! And for good Thai, Chin Chin is boisterous, fun and delicious.

Chin Chin Restaurant | Image: Steven Woodburn

But just before you sit down to a hearty supper, drop in to a few of Sydney’s groovier cocktail bars. Grain—in the Four Seasons lobby—is good fun for first drinks. Then cross George Street and walk a few metres down Dalley Street to find a non-descript door left of a sign saying “Bistecca”. Down the stairs, you enter the secret, candlelit world of an underground speakeasy (connected to Bistecca restaurant), where nice people bring you smooth Negronis. It’s perfect for couples and so dark you can get away with a clandestine cuddle. Nearby, on Harrington Street, Maybe Sammy is where Sydney meets Las Vegas: neon flamingos on the bar, white-jacketed barkeeps and fabulous cocktails (try the Thunderbird).

Bistecca Restaurant

And so to bed, as the last ferries tuck themselves in for the night and the harbour glistens in the moonlight.

The Details


Spontaneity is romantic but it’s worth having a basic plan and booking things in advance, especially restaurants. Also, expect to queue for breakfast. We hate it but it’s a thing here.


May, September and October are probably the best months, avoiding school holidays. If you don’t mind the heat, January is also good because many Sydneysiders are on holiday.


Qantas, Virgin Australia and Jetstar fly to Sydney from pretty much everywhere else in Australia. Buy an OPAL card at the airport and take the train to the city.


The Four Seasons has not only the best beds and views in town but also the largest hotel swimming pool, funky and award-winning cocktail bar Grain and delicious Italian-inspired restaurant Mode. 

Related articles: Road Tripping From Sydney to Byron Bay – Where to Stop, What to See & Do // 40 Unique Romantic Things to Do in Sydney

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