OpinionMark ChipperfieldJune 30, 2026 — 3:34pmIt’s a blustery, overcast day and Sydney Harbour is looking decidedly unglamorous. A westerly wind buffets the Moreton Bay fig trees. Down at Mrs Macquarie’s Chair, a gaggle of cheerful pensioners clad in rain jackets and sensible shoes seek shelter in a big white coach.When everyone is seated Max, head guide of Journey Walks, takes the microphone, casting nervous looks at the drizzle. “Good morning, everyone,” he says. “Welcome to this tour of Kings Cross which begins with a drive around Darlinghurst and then a little walking before we sit down to lunch at Penny’s Hotel where I’ll tell you more about this fascinating part of Sydney.” Photo: Illustration: Jamie BrownAs a trainee guide, my duties today consist of closely observing how Max conducts the tour – and helping some of the frailer participants navigate the byways and laneways of Kings Cross.After 20 minutes traipsing around The Cross, one of the older gents announces that he’s had enough and volunteers to wait for us at the pub. “Sorry lads, but my hips are not as hip as they once were,” he jokes.Failing joints are just one of the many hazards facing the tour guide. Guests routinely wander off, take calls on their mobiles, exchange text messages, or interrupt the commentary with lengthy anecdotes of their own.Sign up for the Traveller newsletterThe latest travel news, tips and inspiration delivered to your inbox. Sign up now.Gathering around the El Alamein Fountain, it becomes clear that some of the women have more personal reasons for joining this tour. “In 1964 I came up here with my girlfriend to catch a glimpse of The Beatles,” whispers one. “But we didn’t go to the concert – our parents wouldn’t have allowed that.”The Beatles, on that balcony.Fairfax ArchivesNow in their ’70s, these suburban grandmothers have a spring in their step as we walk down Macleay Street to the site of the hotel where the Fab Four stayed (and partied) on their first and only tour of Australia. According to newspaper reports a crowd of 300 screaming teenagers, mostly girls, gathered on the footpath opposite.“The hotel was converted to apartments in 1997, but the balcony where the boys were photographed waving at their fans is still there,” says Max.I notice that two of the septuagenarian ravers have a whimsical look on their faces as we stand outside what was once the Chevron Hotel looking up at the famous balcony. Their husbands seem indifferent to these tales of teenage infatuation. Or have they just turned off their hearing aids?Over lunch, the tour group is treated to more salacious details about the precinct’s notorious identities including Tilly Devine, Kate Leigh, Dulcie Deamer, Rosaleen Norton, Bernie Houghton and Abe Saffron.Max is particularly fascinated by brothel-owner Tilly Devine, a leading figure in Sydney’s razor gangs of the 1920s and 1930s. “Tilly drank heavily, dressed flamboyantly and was not afraid to involve herself directly in disputes,” he says.The talk is peppered with references to prostitution, sly grog, murder, arson, corpses and cocaine trafficking but doesn’t seem to offend or disturb our party of history buffs from the southern suburbs.The ladies visibly brighten when Max describes the life and crimes of Louisa Collins who poisoned two husbands, was convicted of murder and hanged at Darlinghurst Gaol in 1889. “When Louisa brought you breakfast in bed you knew your number was up,” he says.I’ve always suspected that tour guiding is much more demanding than it looks. After a couple of hours pounding the streets of Kings Cross, I have a new appreciation of professional tour guides who must keep an eagle eye on their guests, the weather and the clock, while providing erudite and, hopefully, amusing commentary. Tour guides of the world I salute you.More:Travel tipsNew South WalesOpinionSydneyAustraliaFrom our partners