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A day unlike
any other
A luxury private journey into the exquisite Australian countryside.
Welcome to the
Southern Highlands
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.
Quintessential Australian Countryside
The Southern Highlands sits in a sweet spot that few visitors to Sydney ever reach. The air is cooler, the pace is slower, and the landscape, all emerald meadows, granite outcrops and eucalyptus ridgelines, feels a world away from the harbour. This private Southern Highlands tour takes you through the best of it: heritage villages that date to the early colonial era, acclaimed vineyards pouring some of Australia's most underrated cool-climate wines, and one of the state's great natural landmarks. It wraps up somewhere truly special, a working farm where kangaroos roam freely, untouched by the usual tourist trail.
How Your Day Unfolds
A Day in the Southern Highlands
AM
Morning · Pickup & Departure
Sydney to Fitzroy Falls
We collect you from your hotel, Airbnb or cruise terminal and head south down the Hume. Ninety minutes later the city is gone and you are standing at Jersey Lookout above Fitzroy Falls.
Mid
Midday · Villages & Wine
Berrima & Bendooley
Time in Berrima's Georgian main street, then a cool-climate tasting at Bendooley Estate alongside charcuterie and local produce, with the Book Barn next door for lunch.
PM
Afternoon · Bowral & Kangaroos
Bowral to Boscobel
Antiques, boutiques and leafy streets in Bowral, then out to Boscobel, private and exclusively yours for the afternoon, and full of kangaroos as the day cools. Back in Sydney by evening.
Fitzroy Falls
Eighty-One Metres Down
The day opens at one of the most dramatic waterfall lookouts in New South Wales. The water drops from the Barrengarry escarpment into a deep valley of ancient rainforest, spectacular in any season and extraordinary after rain. Jersey Lookout offers the best vantage point and, on a clear day, views across Kangaroo Valley all the way to the coast.
Berrima
Georgian Heritage Village
Australia's most intact Georgian village 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. Unhurried, quietly beautiful, and a reminder that the Southern Highlands has been drawing visitors for a very long time.
Bendooley Estate
Cool-Climate Cellar Door
One of the region's most celebrated estates. The cellar door pours fine cool-climate wines alongside charcuterie plates and local produce, the kind of tasting that slows the day down in exactly the right way. The Book Barn next door is an institution: thousands of secondhand and rare books in a converted stone barn on a working vineyard.
Bowral
Boutiques and Leafy Streets
The social and commercial centre of the Southern Highlands, and a town that rewards a slow stroll. Leafy boulevards, heritage architecture, independent bookshops and excellent cafés line the main streets. It is also home to Dirty Jane's, a sprawling antiques market beloved by locals, and Green Lane, a quiet pocket of boutiques worth finding.
Boscobel Cottage
Wild Kangaroos, Privately
The day finishes somewhere most visitors to the Southern Highlands will never see. Boscobel is a private working property of rolling meadows, quiet forest and absolute stillness, and it is exclusively ours for the afternoon. An afternoon in the open air, and as the day cools, the kangaroos emerge. This is the kind of ending that stays with people.
Transparent Pricing
What's Included
Included
- Private full-day tour (10 hours)
- Hotel, Airbnb & cruise terminal pickup
- Luxury private vehicle
- Bottled water throughout
- Fully tailored itinerary
- Expert local knowledge throughout
- Wine tasting at Bendooley Estate
- Exclusive afternoon access to Boscobel
Not Included
- Lunch & personal expenses
Lunch is not included. We recommend the Book Barn at Bendooley Estate or Harry's on Green Lane in Bowral, and we're happy to book ahead for you. From $1,550 AUD for two guests. Groups from 2 to 14 welcome — contact us for group and corporate pricing.
Guest Reviews
What Our Guests Are Saying
★★★★★
"Best day trip you could possibly do from Sydney, full stop. Wineries, waterfalls, heritage villages, and wild kangaroos on a private farm to finish. The Southern Highlands are amazing and so was this tour. Highly recommend!"— Will H · Google Review
★★★★★
"I booked the Southern Highlands tour as a birthday treat for my mum and it was the best decision. We explored the gorgeous town of Berrima, did some wine tastings at Bendooley Estate, saw an incredible waterfall and then finished at a private farm with so many kangaroos hopping around. My mum was so happy!"— Matt S · TripAdvisor Review
★★★★★
"This was the most fantastic tour we had in Sydney. It is truly spectacular to go to a ranch and see kangaroos, horses and cattle. We visited a nearby stunning waterfall. I highly recommend this company and tour for a special day."— Bryan C · Google Review
Looking for something different? The Blue Mountains deliver ancient sandstone escarpments and hidden waterfalls an hour west of the city. Or stay overnight in the Highlands with the Highland Retreat.
Frequently Asked Questions
Everything You Need to Know
Approximately 10 hours from pickup to drop-off, departing in the morning and returning in the evening. Exact departure times are confirmed at booking.
From $1,550 AUD for two guests. Groups from 2 to 14 guests are welcome — contact us for group and corporate pricing. The price covers your entire private group for the full day.
Included is your luxury private vehicle, hotel or cruise terminal pickup and drop-off, a fully tailored itinerary, expert local guide, bottled water throughout, wine tasting at Bendooley Estate, and exclusive afternoon access to Boscobel. Lunch is not included. We recommend the Book Barn at Bendooley Estate or Harry's on Green Lane in Bowral, and we're happy to book ahead for you.
Bendooley Estate, known for its cool-climate wines, charcuterie and the iconic Book Barn on a working vineyard.
Yes — every tour we run is 100% private, exclusively for your group. No shared coaches, no strangers, and no fixed group schedules. The itinerary moves at your pace.
Yes — pickup and drop-off from hotels, Airbnbs or cruise terminals in central Sydney is included. Just let us know your location when booking and we'll coordinate the timing.
Almost certainly. The tour finishes at Boscobel, where wild kangaroos roam freely across the open meadows, particularly in the late afternoon as the day cools.
Approximately 90 minutes south-west of Sydney via the Hume Highway, making it one of the finest and most accessible day trips from the city.
Yes. The Southern Highlands tour suits corporate groups, conference delegates and executive teams. Groups from 2 to 14 guests are welcome. To discuss a tailored package, contact Alex on +61 468 333 514 or email info@ausadventureco.com.au.
Ready to Explore
the Southern Highlands?
Every journey is tailored around you. Tell us where you'd like to go and we'll handle the rest.