Just 90 minutes south of Sydney, the Southern Highlands is a landscape that rewards those who know where to look. Rolling farmland, sandstone heritage villages, cool-climate vineyards, an 81-metre waterfall, and a private farm where kangaroos emerge at dusk. This is Australia, unhurried and entirely yours.
Just 90 minutes south of Sydney, the Southern Highlands is a landscape that rewards those who know where to look. Sandstone heritage villages, cool-climate vineyards, an 81-metre escarpment waterfall, and a private farm where kangaroos roam freely at dusk.
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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 finest vantage point, with views across the Kangaroo Valley all the way to the coast on a clear day.
Book This TourStop 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 reward a slow wander. It is the ideal first stop of the day: unhurried, quietly beautiful, and a reminder that the Southern Highlands has been drawing travellers for a very long time indeed.
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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.
Book This TourStop Four
Tucked into a quiet pocket of Bowral, Harry's on Greenlane is the kind of place that rewards those who know where to look. A refined stop for lunch or a long afternoon coffee — unhurried, beautifully run, and one of the Southern Highlands' most loved addresses. The surrounds are green and calm, the produce is local, and the pace is exactly what a day like this deserves at its close.
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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.
Book This TourOptional Add-Ons
These experiences can be added to your tour and are not included in the standard tour price.
Begin the day above the Southern Highlands at sunrise, drifting over patchwork farmland and mist-covered valleys. One of the most memorable ways to experience the region, available as an early morning addition before the tour begins.
Tickets can be arranged in advance — just let us know when booking.
Extend your time at Bendooley Estate with a private lunch at the cellar door restaurant — locally sourced produce, cool-climate wines, and a table entirely to yourselves in one of the region's most beautiful settings.
Reservations arranged on your behalf — just let us know when booking.
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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
The tour runs for approximately 10 hours, departing from your hotel or cruise terminal in the morning and returning in the evening. Exact departure times are confirmed at booking.
The Southern Highlands Tour starts from $1,550 AUD for two guests. We can accommodate up to six guests — contact us for group pricing.
Included is your private luxury vehicle, expert guide, wine tastings at Bendooley Estate, private access to Boscobel Farm with local produce and drinks, all entry and tasting fees, and door-to-door pickup and drop-off from central Sydney.
Yes — every tour is 100% private and exclusively for your group. There are no shared coaches, no strangers, and no fixed group schedules. The itinerary moves entirely at your pace.
Yes. Pickup and drop-off are included from central Sydney hotels and cruise terminals. We'll confirm the exact arrangements when you book.
Almost certainly. The tour finishes at Boscobel Farm, a private working property where kangaroos roam freely. As the afternoon cools they typically emerge in numbers — this is not a managed encounter, simply the Australian countryside at its most unguarded.
The Southern Highlands is beautiful in all seasons — misty mornings at Fitzroy Falls are spectacular. In the rare event of severe weather we'll contact you to reschedule at no cost.
Absolutely. Every itinerary is private and can be shaped around your interests. Get in touch before you book and we'll tailor the day accordingly.
Reserve Your Day
Every tour is 100% private — exclusively for your group. No shared coaches, no strangers, no fixed itineraries. Secure your date with a 25% deposit; the rest is paid closer to the time.
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Questions
The tour runs for approximately 10 hours, departing from your hotel, Airbnb or cruise terminal in the morning and returning in the evening. Exact departure times are confirmed at booking.
The Southern Highlands Tour starts from $1,550 AUD for two guests. We can accommodate up to six guests — contact us for group pricing.
Yes. Every tour we run is 100% private — exclusively for your group. There are no shared coaches, no strangers and no fixed group schedules. The itinerary moves at your pace.
The tour includes tastings at Bendooley Estate — known for its cool-climate wines, charcuterie and the iconic Book Barn — and Mount Ashby Estate, a refined working property with French-influenced dining.
Almost certainly. The tour finishes at Boscobel Farm, a private working property where kangaroos roam freely across the paddocks. As the afternoon cools, they typically emerge in numbers — this is not a zoo or a managed encounter, simply the Australian countryside at its most unguarded.
Yes. Pickup and drop-off are included from central Sydney hotels and cruise ship terminals. We'll confirm the exact arrangements when you book.
Absolutely. Every itinerary is private and can be shaped around your interests — whether you'd like more time at the wineries, a longer walk at Fitzroy Falls, or something else entirely. Get in touch before you book and we'll tailor the day accordingly.
