Context Private Tours: Inside Guides to Sydney

LUXE has partnered with pride of guides Context Travel, who run private and small group tours led by an armed cotillion of art historians, PhDs, culture mavens + specialists. They’ll enlighten you via themed itins or bespoke jaunts, so you can spend time taking in the sights, not with your head buried in a book. What’s more, now you can book tours directly through our app. Glam gallivants ahead!

Welcome to Sydney 

Acquaint yourself with the Oz’s Emerald City through a tailored, local-led consultation and exploration.

OK. So you know about the Opera House and Bondi Beach, but need a little extra assistance when it comes to Sydney’s finer points? No worries, mate. Book an orientation experience through Context Travel and they’ll dispense one of their in-the-know resident guides right to your abode.

Over two hours you can grill them like a shrimp on the barbie for inside intel on all of this harbour town’s best bits, from top shops to fine dine restos and great places to down a schooner – they’ll even help you decipher the local lingo so you know what that means. Too easy!

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Making of Sydney 

From far-flung penal settlement to sparkling harbour dazzler, Syders has come a long way in two centuries, and this tour walks you through it all.

Ah Sydney, Oz’s Emerald City. These days she’s a thoroughly modern metropolis with amazing architecture and an enviably laidback lifestyle, but this beach babe also has a strong historical side that’s certainly worth exploring.

On this three-hour amble led by a local heritage researcher, walkers will learn about the city’s early history, from its place in the lives of indigenous aboriginal peoples to colonisation, Federation and beyond.

Set off from Circular Quay, where the First Fleet first landed, and stroll along the harbour on to such historical sites as the Museum of Sydney (sitting on the site of Australia’s first Government House), Hyde Park Barracks, St. James Church, and the King Street Law Courts.

From the city’s development (here’s lookin’ at you, Mr Macquarie) to convict emancipation, classism and racism, migration and modernisation, no subject is off topic with these expert insights.

Insider Tip: The tour ends in the leafy and lovely Hyde Park putting you but a skip from post-saunter sup and sipsters Bambini Wine Room and Sagra. Well deserved!

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Beyond Pho 

Discover Sydney’s Saigon side on this foodie frolic through the vibrant south-western suburb of Cabramatta.

Through the second half of the C.20th, Southeast Asian immigration flowed like the Mekong river into Sydney, saturating the city’s culinary scene with spicy niceties. Why not raise a glass of green tea to this cultural fusion with a taste-bud tingling walking tour through the outlying suburb of Cabramatta aka Little Vietnam?

You’ll feel transported to Hanoi as you amble through the exotic aisles of the ‘Cabra’ Market and surrounding resto-packed streets with a few fellow foodies, grazing on rambutans as your local gourmand guide explains how this Oriental outpost came to be. And to finish your three-hour jaunt? What else but a bowl of Vietnam’s soupy, national noodle dish. Pho-nomenal!

Insider Tip: For a Ho Chi Minh much closer to town, try Misschu Bondi Tuckshop for perf paper rolls and banh mi.

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Convicts, Strumpets, and the Plague 

Get to grips with The Rocks-ing social history of Sydney on a tour of the area that’s seen it all.

From prisoners and prostitutes to razor-wielding gangs and rough n’ ready workers, Australia in its early colonial years was crammed with colourful (and not infrequently criminal) characters and nowhere more so than the hood where it all started, The Rocks.

It was here, at Sydney Cove (aka Circular Quay), that the First Fleet landed and your three-hour jaunt begins. Following an Oz history professor, walkers will learn about the area’s original indigenous inhabitants, the Cadigal people, discuss convict and early settler history and visit important sites including Cadman’s Cottage and The Big Dig archaeological centre – home to what’s left of some of Australia’s first houses, streets and shops.

The tour then takes in the narrow, picturesque alleyways that crisscross around the ‘coathanger’, exploring the impact that successive waves of immigrants – from European ‘dockers’ and labourers to C.20th Chinese merchants and even the wildly successful strumpets (prostitutes) – had on the development of The Rocks and the city in general.

Insider Tip: For more historic hijinx visit the nearby Susannah Place Museum, a series of largely unchanged terraced houses – complete with brick thunderboxes – that were built by C.19th Irish immigrants and have housed Syd’s working class families for some 150 years.

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Eleani Purcell

Having spent the better part of her 'study years' flitting from Sri Lanka and South Africa to Iceland and Italy, Eleani joined LUXE fresh from freelancing for TimeOut Melbourne and Fairfax media. 

  • Eleani LOVES... Books by Jon Krakauer, orca documentaries, forecasting jaunts to Japan, Java, Cuba and Zanzibar

  • Eleani LOATHES... Aeroplane headphones, haggling

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