The Southern Highlands is one of New South Wales' best-kept secrets - and one of the finest day trips from Sydney. Just 90 minutes south of the city, rolling countryside gives way to sandstone heritage villages, cool-climate vineyards, dramatic escarpment waterfalls and private farmland where kangaroos graze at dusk. This is a 10-hour private day tour designed for guests who want to experience the Australian countryside properly.
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Stop One
At 81 metres, Fitzroy Falls is one of the most dramatic waterfall lookouts in New South Wales. The water drops from the Barrengarry Gorge escarpment into a deep valley of ancient rainforest below — spectacular in any season, extraordinary after rain. The Jersey Lookout offers the best vantage point and, on a clear day, views across the Kangaroo Valley all the way to the coast.
Stop Two
Australia's most intact Georgian village, Berrima has barely changed since the 1840s. Sandstone courthouse, colonial gaol, historic inn — and a main street of galleries, providores and cafés that make it worth lingering. It's the ideal first stop: unhurried, quietly beautiful, and a reminder that the Southern Highlands has been drawing visitors for a very long time.
Stop Three
One of the Southern Highlands' most celebrated cellar doors. Bendooley pours fine cool-climate wines alongside charcuterie and local produce — the kind of tasting that slows the afternoon down in exactly the right way. Next door, the Book Barn occupies a converted stone building on the working vineyard: thousands of secondhand and rare books, and a destination entirely worth visiting on its own.
Stop Four
Harry's on Green Lane is one of Bowral's most charming dining spots, tucked behind an antique-filled laneway and surrounded by lush greenery, old-world interiors and quiet Southern Highlands character. It is the perfect place to pause for a relaxed lunch or coffee, with a warm, elegant atmosphere that feels distinctly local. Afterwards, guests can wander next door to Dirty Janes, a beautiful antiques and vintage market made for pottering, browsing and discovering hidden treasures.
Stop Five
The day ends somewhere most visitors to Australia will never find. Boscobel is a private working farm — rolling meadows, ancient trees, absolute stillness. As the afternoon light softens and the air cools, the kangaroos emerge across the paddocks. Cold drinks, local produce, and the kind of quiet that only the Australian countryside can offer. This is the ending that stays with people.
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Guest Reviews
"From pickup to drop-off, Sam delivered a day that exceeded every expectation. Unhurried, knowledgeable, and genuinely passionate about the region. The farm at the end was something we'll never forget."
— The Morrison Family · Google Review
"We had no idea the Southern Highlands was this beautiful. The whole day felt completely personal to us — every stop was perfectly chosen. Bendooley and Fitzroy Falls alone were worth the trip."
— Sarah M. · TripAdvisor Review
"Genuinely one of the best days of our Australia trip. The kangaroos at dusk at Boscobel Farm — we still talk about it. A guide who actually knows and loves what they're showing you makes all the difference."
— James & Family · Google Review
