Bondi Bliss, Cool-Climate Wine, and Pacific-Coast Reprieves: The 4-Day Weekend in Sydney, Australia

Sydney Australia
Jan Kratochvila / Shutterstock

Even when you’re in Sydney, it feels like a postcard. You’ve long imagined what those famous scenes would look like in person—the opera house, Harbour Bridge, and the Bondi Beach sprawl (as well as that famous lap pool overlooking the coast that’s all over Instagram). And when you’re there, Sydney still feels surreal—true to your expectations. It’s like your first visit to San Francisco, Tokyo, London, or Rio.

But there’s more to Sydney than its wildly popular attractions. You have the sprawling coastlines of New South Wales in either direction, plus cool-climate vineyards to explore; it all makes for one helluva retreat away from the city bustle. Plus, after that long flight (or before your return haul), a city escape is one way to savor your investment in coming all this way. They’ll leave an indelible imprint on your brain as you plot your inevitable return.

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How to Get There

Sydney is Australia’s hub for international flights, and in particular those coming from North America. You can get there on Delta, United, American, Hawaiian, Alaskan—and can find direct flights from LA, SF, Honolulu, Houston, and Dallas. Two major Australian carriers are also good options: Virgin Australia, (a Delta and Virgin Atlantic partner), as well as Qantas, part of Oneworld Alliance. Qantas famously flew a record-setting 19-hour non-stop flight from New York to Sydney in 2019, though that distance hasn’t been cleared for passenger use. So for now, you’ll have to settle with a southern or western layover, and a 15+ hour haul from there.

Paramount House Hotel
Paramount House Hotel Courtesy Image

Where to Stay

Paramount House Hotel: Far more than just a hotel, Paramount House feels like Sydney’s core meeting ground for the culturally tuned, wellness fueled, creative class. First of all, its rooms look like homes we would actually strive to live in. There’s no streamlined hospitality at play here. (Nice touch on the Aesop amenities, too—a favorite grooming brand that happens to be anchored in Australia.) Onsite at Paramount, you’ll find a rooftop recreation club, vintagey cinema, buzzy wine bar (with A+ bites), and freelancer-friendly coffee shop. Paramount is a hipster enclave in the heart of Surry Hills (OK, that neighborhood itself is the enclave, but Paramount best waves the flag). They never go overboard with the hipsterdom, though (think those hilarious Ace Hotel spoofs in Portlandia). There’s no pretentiousness at Paramount, no exclusivity—and, for that, it’s a warming start and end to each day in Sydney.

Ovolo Woolloomooloo: Ovolo Woolloomooloo is a mouthful to say, and its property matches that name in pure oddity: Inhabiting a former wharf passenger terminal, Ovolo Woolloomooloo is, essentially, housed inside an old shipping dock. A grand, open foyer invites dining guests. You can peek out over the waters of the wharf, or march the length of it to the property’s gym and pool. The aesthetic is odd and endearing, all the way down to the rock-music detail that makes its way into Ovolo’s decor. It’s 5-star boutique and yet cheeky all at once, and the property is unlike anywhere else you’ll ever stay. For that, it’s certainly worth the visit. As an added perk, the property is next to the botanic garden, which itself is the gateway to the Sydney Opera House. It’s one of the more memorable walks you’ll have in your life.

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QT Bondi Beach: While Bondi is somewhat removed from the rest of Sydney, it’s likely for travelers to anchor themselves there—even just for a night—in order to experience the beach-bum vibes. If you crash here, do it at QT Bondi Beach, so you have instant access to the beach, as well as a homey boutique room to welcome you back. While most other QT properties in Australia have a 5-star aim, QT Bondi Beach finds its groove with a 4-star, laidback property. There’s no private hotel gym nor an onsite restaurant, but they do partner with an adjacent fitness center and a neighboring restaurant to provide you those luxuries.

Bondi Beach in Sydney
Bondi Beach in Sydney Daniel Boud/Destination NSW

What to Do In and Around Sydney

Sydney Opera House: Here’s that Sydney postcard shot—finally you can see it in real life. But go one step further and book a tour of the Opera House for access to its various performance halls and events spaces, as well as to learn about its history and construction. Please note that the main hall is undergoing major renovations, with an estimated reopening of late 2021 or early 2022.

Bondi: A day (or more) in Bondi is requisite for your visit. This is where all Sydneysiders escape for a dip, a tan, a Pacific coast hike (if you dare, you can do the full Bondi to Coogee walk), or even a more purposeful swim at the Instagram-famous Bondi Icebergs Club lap pool. On Saturdays, you can snack your way through the Bondi Farmers Market, and on any day of the week, you can meander the side streets and step into Bondi’s numerous clothing shops, bookstores, cafes, bars, and more.

Explore New South Wales: Sydney’s great, but you came all this way—and are a short drive from sprawling beaches and cool-climate wineries, so why not skip town for a night or two? You can stop en route at the Kiama Blowhole (the world’s largest blowhole), and set your sights and overnights for Bangalay Luxury Villas or The Range at Dovecote. The former is a fenced-in villa on the remote Shoalhaven Heads coastline (and its soul-soothing beach). Its onsite restaurant serves up a gourmet tasting menu paired with regional wines. The latter is an isolated, cinematic reprieve above the highlands coast, with dramatic details and sprawling landscape and seaside views (as well as a private gate that leads to the beach. Both options bring you close to Booderee National Park with its white sand beaches, high cliffs, and botanic gardens; they’re also near Beecroft Peninsula, which is perfect for whale watching and eagle scouting. Round out your visit through NSW by booking a private tasting tour of the Southern Highlands wine region with The Highlands Tour Co., and they’ll make sure you arrive safely to each leg of the trip: Ideally, it’ll include Tertini and Centennial vineyards, among others in the high-altitude, cool-climate region. Between a wine day and a beach day—plus the attractions en route, budget at least two nights in southern NSW before returning to Sydney.

The Royal Botanic Garden
The Royal Botanic Garden Taras Vyshnya / Shutterstock

Creative Enclave Tour: While Melbourne may have the reputation as Australia’s creative capital, Sydney puts up a good argument. And the Culture Scouts team leads tours through the renewed inner-city precincts, like the Chippendale neighborhood, or through Sydney’s CBD, taut laneways, and gallery district. You can book public tours or customize your own private excursion if there’s some specific aspect of Sydney you want to explore, like its best bars and restaurants.

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The Royal Botanic Garden: Discover the myriad flora that compromise the royal family’s collection. (And some fauna too—look up!) This is adjacent to the Opera House, and a slow, sauntering walk is easy to combine with your visit there.

Art Museums Between the Art Gallery of NSW and Museum of Contemporary Art, you’ve got two world-class museums to fill an afternoon. Have a look at the exhibitions calendar to see what’s on.

Campfire martinis at Hyde Hacienda
Campfire martinis at Hyde Hacienda Courtesy Image

Where to Eat and Drink in Sydney

Chin Chin: This in-demand Surry Hills restaurant is inside the heritage-listed Griffiths Tea Building, and serves up modern Asian fare with an Australian spin.

Botanic House: Botanic House is tucked into the foliage of Sydney’s remarkable botanic garden. Chef Luke Nguyen is Thai born, and of Vietnamese and Chinese descent, and he combines all these, as well as other South East Asian flavors.

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Hyde Hacienda: South American flavors, live music, Harbour Bridge views, and a Cuban-Miami ambiance.

Totti’s Bondi: Top-notch Italian underneath olive trees (if you’re seated on their patio). Totti’s is the latest opening from Sydney’s most prominent restauranteurs, the Merivale group. Like any of their spots, be sure you book in advance.

Bill’s Bondi Beach: For nearly three decades, all of Bill Granger’s restaurants have come to characterize Australian dining—fresh, flavorful, friendly, familial. This one fits right in with the Bondi buzz, but be sure to track down his other locations around Sydney, Seoul, Tokyo, Honolulu, and London.

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