A 3-day romantic break in Sydney

Afternoon  

Check in to the city’s newest boutique luxury hotel, The Eve, which opens in February. Part of the new $500 million Wunderlich Lane dining precinct on the border of Surry Hills and Redfern, it’s an architectural gem with lush climbing gardens, rich textures, an impressive art collection and more than a handful of cool new restaurants and bars. Be sure to arrive early enough for a swim in the rooftop pool, surrounded by retro cabanas and palm trees. Toast the start of your romantic escape with a cocktail from the poolside bar. 

The Eve Hotel - Credit: Georg Roske

Evening 

It’s just a 10-minute stroll along Crown Street for dinner. The White Horse has been a Surry Hills landmark for decades, but a $6 million renovation has transformed it into something entirely new. The ground floor is now a fine dining restaurant that was awarded a coveted chef’s hat in the 2025 Good Food Guide. There’s a focus on ethically sourced produce and local flavours, but at a more reasonable price point than your usual hatted venue. 

The White Horse, Surry Hills - Credit: White Horse

If you’re not ready for bed, it’s another short walk to The Art Syndicate, an innovative wine bar and gallery in Taylor Square. This intimate space seats just 25 and serves wine, beer and spirits only from NSW. It’s designed to cultivate community and conversation, so you may find yourself chatting to other guests about art, wine and everything in between.  

The Art Syndicate - Credit: Lexi Potts | The Art Syndicate

Morning 

It’s a (very) early start this morning, but we promise it will be worth it. Be on the water as the city wakes with a sunrise kayak tour with Sydney by Kayak. Setting off from Lavender Bay boat ramp at 5am, you’ll paddle beneath the Sydney Harbour Bridge just as the sun begins to peek above the horizon. 

Kayaking on iconic Sydney Harbour

Afterwards, refuel with the fluffiest focaccias and exquisite pastries at AP Bakery on the rooftop of Paramount House Hotel. Our pick is the macadamia, honey and thyme twice baked croissant.  

Soothe those paddling muscles with a visit to Capybara Bathing, a new wellness centre in Surry Hills. Sweat it out in the steam room or hot stone sauna, soak in the magnesium pool, then finishing with a bracing dip in the cold plunge. 

Capybara Bathing - Credit: Declan Blackall Photography

Afternoon  

Head into the city for some cultural connection this afternoon. Wander through the hallowed halls of the 150-year-old Art Gallery of NSW, then marvel at the contrast of the striking new Sydney Modern building, a masterpiece in itself. Or visit the harbourside Museum of Contemporary Art to see the country’s only public collection dedicated to living artists, with more than 4,500 works on display. 

People visiting the Art Gallery of New South Wales, Sydney 

Evening 

As the sun sets, grab a drink at The Library Bar. This open-air hidden gem on the roof of the State Library has gorgeous views over the harbour and Domain. For dinner, are you feeling fancy or looking for something a little more laid back? The two-hat Allta takes Korean food to a new level, serving a luxe 15-course degustation menu to just 12 guests each night. Or book a table at King Clarence, where the vibe is more relaxed and the menu playful. It also holds two hats, but expect dishes like fish finger bao buns and Vegemite toast with chicken liver skewers, plus a disco ball-lit private dining room and DJs from Wednesday to Sunday evenings. 

The Library Bar, rooftop of the State Library of NSW

There’s still time to catch a show or a live performance tonight. Sydney has a calendar jam packed with musicals, theatre, dance and music, held everywhere from iconic venues like the Sydney Opera House to underground jazz bars. Check our events calendar to find something you’ll love. 

On the steps of the Sydney Opera House

Morning 

Enjoy a well-deserved sleep in this morning, then head to the roof for another swim. Bar Julius in The Eve’s hotel lobby is open early for coffee and breakfast. 

Then it’s time to explore Sydney Harbour in the most romantic way possible. You’ll feel like an Italian movie star on a private cruise aboard a chic Venetian-style boat. Choose the MV Bel, operated by Sydney Luxury Cruise, or La Dolce Vita and zip past the city’s most famous sites while sipping a glass of bubbly. 

La Dolce Vita - Credit: Steve Bach | Any Boat Pty Ltd

Afternoon  

Ask your captain to drop you off at Balmoral Beach, where it’s time for a quick dip and a long lunch at the heritage-listed Bathers’ Pavilion. Get a seat by the window at the relaxed Bathers’ Bistro and feast on freshly shucked oysters, grilled octopus, prawns with garlic butter and pan roasted barramundi fillet. Afterwards, pick up an artisan ice block from the kiosk and take a walk along the beach. 

Bathers Pavilion, Mosman 

Evening 

The weekend is almost over, but there’s time for one more showstopping dinner. Indigenous chef Mark Olive (also known as The Black Olive) has opened Midden restaurant on the western boardwalk of the Sydney Opera House. The views are to die for, but it’s what’s on the plate that makes this place really special. The unique menu highlights native ingredients like lemon myrtle, saltbush, wallaby and crocodile. Finish the meal with Mark’s signature bush pavlova topped with native fruit coulis and wattleseed cream. 

Take a last stroll around the harbour, admiring the city lights glittering over the water – the perfect end to your romantic escape. 

Midden by Mark Olive - Credit: Midden by Mark Olive