Ruby O'Connor

Ruby O’Connor is a listener first. Thirteen years into her career as a luxury travel advisor with Travel Associates, she has built her reputation on translating loose ideas into bespoke journeys her clients describe as exactly what they wanted – even when they couldn’t quite say so themselves. “I try to read between the lines and hear what they’re seeking from a holiday,” she says. “Sometimes things they’re not even sure of themselves yet.”

That instinct is matched by an appetite for the world that has yet to slow down. Across 34 countries, Ruby has chased gyros through the Greek Islands, snowmobiled across Niseko’s mountains, played at being royalty for a night at Hyderabad’s Taj Falaknuma Palace, and flown doors-off over Kakadu in pursuit of wild horses. “There’s a favourite memory from every trip,” she admits – each one informing the itineraries she now builds for others.

Her expertise leans toward destinations with depth, places that reward curiosity. Vietnam has long been a favourite, and Sri Lanka has more recently joined the top of her list. “Both tick so many boxes,” she says. “Wildlife, food, adventure, culture, history, the wonderful people, gorgeous beaches. I could keep going.” Beyond Asia, she’s a specialist in Italy, the UK, Fiji, Antarctica and the wildlife landscapes of South Africa, with particular expertise in ultra-luxury cruising, expedition voyages and small-group touring.

She is also a problem-solver of the highest order. For one client embarking on their first ultra-luxury cruise, Ruby replaced a long, dusty drive between Broome and Exmouth with a private scenic flight – turning a logistical headache into a bucket-list moment. It’s the kind of thinking that has earned her a loyal following across luxury travel in Australia.

Next on her own list? Antarctica, paired with the South American adventure she’s been saving for the right moment. Her advice for anyone planning a one-of-a-kind holiday is refreshingly simple: “Don’t overthink it. There are infinite ways to execute your dream trip – sit down with a trusted travel pro and let us curate it for you.”