Introducing a series of alternative city guides, specially curated for the cultivated traveller.

After travelling to the other side of the world, it can be a little disorientating to land in Sydney and find it so familiar. It’s a city that reminds you of other cities; the dense, skyscraper-lined avenues of the business district recalls Chicago or Manhattan. The sandstone Victorian architecture and red-brick warehouses of the centre are at times uncannily reminiscent of Manchester or Glasgow. The area around Oxford Street, with its dainty low-rise streets, looks a bit like San Francisco, while Newtown, a neighbourhood of shady dive bars, lush foliage and Creole-style townhouses, has a similar feel to New Orleans.

But so much about Sydney is unique. For a start, it would be hard to overstate the splendour of its setting: worlds failed even Victorian novelist Anthony Trollope, who in 1883 wrote, “I despair of being able to convey to any reader my own idea of the beauty of Sydney Harbour,” adding that no other scenery in the world came close to possessing such a “world of loveliness of water”. The natural life is so lush and bounteous that Sydney at times feels like a paradise. The architecture of its older districts, such as the Rocks, conjures up a history which is entirely its own – it’s easy to imagine it when it was still an impossible remote outpost of the British empire. And while the country still has many problems with how it treats its Indigenous communities, Sydney’s cultural institutions display an admirable commitment to exploring its own colonial past, and to showcasing Aboriginal or First Nation culture – something which is consistently among the most fascinating aspects of its museums and galleries.

Below, you’ll find a selection of the best attractions in Sydney, along with the best places to eat, sleep and drink.

Walks

Sydney Botanical Gardens

Easily accessible from the centre, this is a great place to go for the most iconic views of the city: if you walk to the end, in one direction you can see the Opera House with the Harbour Bridge looming behind, and in the other, the skyscrapers of Downtown (which look more impressive from afar). In contrast to the rugged landscapes you’ll find elsewhere, The Botanic Gardens are immaculately curated and elegant in a grand, Victorian way, teeming with ornate statues and elaborate floral arrangements. There is a trace of the exotic in both the plant life and the avian presence: while there are all sorts of weird and wonderful birds hopping around, I fell in love with the ‘white ibis’ – a long-beaked creature known referred to by locals (affectionately but, I thought, with a touch of disrespect) as the “bin chicken”.

Wendy Whiteley’s Secret Garden

On the other side of the harbour, you’ll find Wendy Whiteley’s Secret Garden. Whitelaw – a local artist – began the project back in 1992, having turned to horticulture for solace following the death of her husband. Offering breathtaking views across the water, it is a peaceful and contemplative place, home to parrots and kookaburras; cobbled stairs, statues, picnic benches, and an eclectic range of plants and herbs.

Bondi to Coogee Walk

Heading south from Bondi Beach (itself a little underwhelming, relative to its iconic status), you’ll find one of the world’s most beautiful stretches of coastline. Parts of it have an almost tropical verdancy, but there’s also something wild, windswept and forlorn about it – more Northumbrian than Carribean. It really does feel like the end of the world which, in a sense, it is.

Along the route, you pass several beaches, coves and inlets (the tiny, tucked-away Gordan’s Cove was my favourite). The highlight is Waverley Cemetery: set on a hill, its statues, mausoleums and rows of white marble face out towards the ocean.

Restaurants

Blackwood

Back in Newtown, Bloodwood is one of the hippest small plates restaurants in Sydney. It has everything you could want from such an establishment: neon artwork on exposed brick walls; hanging lights in the shape of birdcages, a playlist of tasteful, unobtrusive house music; a clientele of well-heeled young Sydney-ites; natural wine, cocktails, and great food. While they do serve meat, the vegetarian options are particularly good: try the ‘chickpea pancake’, a surprisingly hearty, pizza-like dish served with peppers and feta cheese.

Cafe Freda

Cafe Freda overlooks a square at the edge of Sydney’s gay district, an atmospheric street lined with neon lights, murals and a range of bars from the trashy to the classy. It’s a suitably fun location – Freda is relaxed and airy, with ample outdoor seating, a fabulous pink decor and a rotating display of local artists on the walls. The menu offers a mixture of small and large plates, almost all of which are made with local ingredients – the heirloom tomato and peach salad is delicious.

Chinatown

Sydney’s Chinatown is especially picturesque: there are overhanging eucalyptus trees and ceremonial arches, while the nearby ‘Garden of Friendship’ has both a waterfall and an enormous pagoda. It also offers a superlative range of dining options. options. For a quick snack, I’d recommend Dragon Pastry, a recently opened bakery that offers sweet desserts and savoury bites. For a more substantial meal, check out Chinese Noodle Restaurant, which very much does what it says on the tin – the hand-pulled Xinjiang noodles, in particular, are exquisite.

Bars

Shady Pines Saloon

This speakeasy bar is hard to find but worth the effort. After descending a steep flight of stairs, you find yourself in a cowboy saloon straight out of Tennessee, with sultry lighting, country music blaring on the speakers, and stuffed buffalo heads mounted on the walls. That might sound tacky, but the design is so well-considered that it transcends what could easily have been a gimmick. The cocktails are also excellent – I’d recommend the ‘Goldie Griffiths’, made with pineapple and whiskey.

Moya’s Lounge

Redfern is one of Sydney’s coolest inner-city neighbourhoods, and Moya’s is the jewel in its crown (or at least one of many). Lit with antique lamps and set to a playlist of old-timey jazz and blues, the atmosphere is inviting and sophisticated. The bar stocks over 280 brands of gin, and almost all of its garnishes are made in-house.

Botany View Hotel

There is an abundance of cool bars and pubs in Newton – which, if you wanted to be reductive about it, is Sydney’s answer to Hackney or Brooklyn – and Botany View is one of the best. It’s both typical of an Australian drive bar and charmingly eccentric (at least to an outsider’s eye), thanks to its Art Deco signage, carpeted floor and collection of vintage arcade games. It hosts a regular schedule of live music, and there is a spacious rooftop bar upstairs which makes it the perfect place to pass a hazy summer afternoon.

Museums & Galleries

Museum of Contemporary Art

Housed in a grand art deco building, the MCA offers a concise snapshot of contemporary Australian art. While the space is relatively compact, it displays an eclectic and wide-ranging mixture of photography, paintings and video installations. There is also a strong focus on Indigenous art, much of which utilises traditional Aboriginal techniques: the Arnott’s collection of bark paintings, created between the 1960s and 1980s, is particularly fascinating.

Art Gallery of New South Wales

The largest of Sydney’s galleries, the Art Gallery of New South Wales is divided into two halves: the neo-classical Vernon building is devoted to classic art, while the Captain Cook Building (along with a handful of extensions) displays work from the 20th century onwards. The influence of Aboriginal culture is felt deeply in Sydney, and what I found most interesting about the gallery’s modern sections was how generation after generation of Australian artists – whether Indigenous or not – had been inspired by its traditional practices.  The biggest revelation, for me, was the work of Sidney Nolan, a mid-20th-century artist who made surreal, foreboding paintings representing scenes from Australian folklore – many of them haunted by a jet-black figure with a square head and ambiguous, shifting eyes.

The Powerhouse

The Powerhouse is somewhat uncategorisable – it’s technically a science museum but there’s a strong focus on design and the decorative arts, making it closer to an institution like the V&A. While the permanent collections fall more on the science side, the temporary exhibitions are broader in scope, exploring themes at the cutting edge of contemporary Australian culture.

Hotels

Pier One

Pier One is located in one of the best spots in Sydney, right on the harbour and directly underneath the bridge. It is part of a complex of renovated military barracks, which includes a whole strip of theatres; the Australian Chamber Orchestra, the Sydney Dance Company, and several bars and restaurants.

The hotel itself is the epitome of industrial chic, albeit with a maritime twist. The building makes excellent use of its historic design features, and there is a range of high-end dining and bar experiences. Based on the ground floor, Pier One offers great views across the pier and a high-end menu with a particular emphasis on fresh seafood and seasonal ingredients. For a unique luxury experience in the heart of the city, Pier One is among the very best Sydney has to offer.

W Sydney

If Pier One offers a timeless, old-world elegance, the W is at the opposite end of the spectrum: housed in a gigantic new building, it is bold, riotous and futuristic. But the hotel has more than just sheer scale on its side, and while the design features are colourful and eclectic, the effect is never garish. Every element has been painstakingly curated to reflect the hotel’s theme: ‘larrikin’, an old Australian slang word to describe someone with a disregard for convention. From the copper-coloured escalator at the entrance, to the undulating constellation of lights on the corridor ceilings (designed, like much of the W, in collaboration with a local artist,)  to the maritime-themed rooftop bar and its adjoining vertical pool, it provides an endlessly immersive design experience.

There are a number of bars and restaurants located inside the W, but the stand-out is BTWN. Decorated with graffiti by local street artists and sandwiched between two freeways, the atmosphere is vibrant and urban, while the menu offers an inventive spin on modern Australian cuisine. I’d recommend the oysters (there are three different types from across New South Wales), the kangaroo tartare, and the tuna teriyaki with pickled cucumber and soft cheese.

Moxy

Located right by the airport, the Moxy is a great place to spend the night on your way in or out of the city and a fun place to hang out in its own right. Bar Moxy is chic and spacious, offering a great selection of signature cocktails, vintage furniture, a 1970s-style photo booth, and a Lebanese-inspired food menu. The rooms are stylish and comfortable, and have all the amenities you could possibly need.