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Discover the Southern Highlands’ best wineries on this guided tour from Sydney, featuring scenic views, exclusive tastings, and seamless transport.
Exploring the Southern Highlands: A Wine Lover’s Day Out from Sydney
Our review of the Sydney Wine Tasting & Southern Highlands tour introduces you to a well-curated day trip that appeals to wine enthusiasts and curious travelers alike. While we haven’t experienced it firsthand, the detailed itinerary, glowing reviews, and thoughtful design suggest this is a fantastic way to enjoy some of New South Wales’ top cool-climate wines, all within a manageable day trip from the city.
What we love about this tour is the focus on quality wineries and scenic countryside, which combine to create an authentic and relaxed experience. The fact that it’s a private guided tour with door-to-door pickup and drop-off makes it especially appealing for those wanting a hassle-free, personalized day. A potential consideration is that the tour’s price of around $283 per person is on the higher side, but it includes tastings and private transport, which often adds value. This experience suits wine lovers, couples, corporate groups, or anyone celebrating a special occasion who wants a taste of the countryside without the hassle of driving.

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Your journey begins at Centennial Vineyards, set in the heart of the Southern Highlands. This winery is known for its award-winning cool-climate wines and stunning natural surroundings. We loved the way the estate combines sophisticated wine production with a welcoming atmosphere. The tasting here lasts about an hour, giving you ample time to savor a variety of wines and soak up the picturesque scenery. The included admission ensures you won’t need to worry about extra costs, and the estate’s reputation for hospitality makes it a perfect start.
Next, the tour takes you to Peppergreen Estate, located in the historic village of Berrima. What makes this stop special is not just the wine—made from premium local grapes—but also the elegant setting and artisanal experiences on offer. You’ll spend about an hour here, tasting sophisticated wines and enjoying the estate’s charm. The estate’s blend of history and modernity makes it a memorable part of the day.
A highlight for many visitors is Bendooley Estate, famous for its beautifully restored Georgian homestead and a renowned restaurant. Beyond the wines, the estate’s literary vibe, with its impressive Book Barn, adds a unique dimension to the visit. The estate’s vineyard and elegant surroundings make it a great spot for both tasting and relaxing. The hour spent here offers a nice balance between wine and scenery, perfect for photo ops and a chance to unwind.
For those who appreciate small-batch, handcrafted wines, Artemis Wines is a real treat. Its boutique nature means you’ll often find wines that embody elegance, balance, and a true sense of place—qualities that wine enthusiasts seek. The 45-minute tasting provides a focused, intimate experience, leaving you with a good sense of the region’s craftsmanship. It’s a quieter, more personal stop that highlights the region’s dedication to quality over quantity.
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Around midday, you have about an hour for lunch. Options range from eating at Peppergreen Estate, Centennial Vineyards, or Bendooley Estate, or exploring Bowral’s local cafes and pubs—ideal if you’re craving a more casual meal or a quick local bite. Many appreciate the flexibility here, as it allows you to tailor the experience to your preferences, whether that’s a fine estate lunch or a laid-back pub meal.
The day concludes with a 1.5-hour drive back to Sydney’s CBD, during which your guide will take care of the driving. This relaxed return gives you time to reflect on the day’s highlights, whether that’s a favorite wine, a lovely view, or a charming village. The door-to-door service means no stress about transit or parking, making it a smooth end to your day.

At $283.31 per person, this tour packs in a lot: private transport, multiple high-quality winery visits, and ample tasting opportunities. While the price may seem steep, consider that it includes admission to each winery and tastings, which can otherwise add up if you visit independently. Plus, the convenience of private pickup and drop-off and a dedicated guide saves you both time and effort, allowing you to relax and enjoy the day fully.
The experience also offers a lot of flexibility—whether you want to focus on wine, enjoy scenic views, or explore local villages. The fact that it’s a private tour ensures a more personalized experience, away from large crowds, which many travelers find adds to the enjoyment.

The only available review, calling the tour an “Excellent tour” and stating, “will do again!,” emphasizes the positive perception. The reviewer appreciated the guide and the wineries visited, mentioning that they had a terrific day and visited incredible wineries. Such feedback suggests high satisfaction, especially for those who love quality wines and scenic drives.

This experience is ideal for wine enthusiasts eager to explore New South Wales’ cooler climate varieties. It also suits couples seeking a romantic escape, groups of friends wanting a relaxed day out, or corporate teams celebrating milestones. The flexible lunch options and intimate setting make it versatile for different occasions.

The Sydney Wine Tasting & Southern Highlands tour offers a well-rounded, convenient way to taste some of Australia’s finest wines while enjoying stunning countryside. Its thoughtful design—private transport, multiple boutique wineries, and scenic stops—creates a memorable day for lovers of wine and beautiful landscapes alike.
While it comes at a premium price, the inclusiveness of tastings and ease of logistics offer strong value, especially for those wanting a stress-free, guided experience. Whether you’re a seasoned wine connoisseur or simply looking to enjoy a taste of rural charm, this tour is a worthy option.
In sum, if you’re after a relaxing, informative, and scenic winery tour close to Sydney, this private Southern Highlands experience promises a day full of flavor, views, and good company.
“We had a terrific day with Kookaburra Tours. Joey was an excellent guide, and took us to some incredible wineries. Thank you, will definitely do th…”

Is transportation included in this tour?
Yes, the tour features private pickup and drop-off from your Sydney CBD accommodation, along with transportation between wineries.
How long is the total tour?
The entire experience lasts approximately 8 hours and 30 minutes, including stops and travel time.
Are tastings included?
Absolutely. Wine tastings are part of the tour at each winery, with admission tickets included.
Can I choose where to eat lunch?
You have the option to eat at the wineries—Peppergreen Estate, Centennial Vineyards, or Bendooley Estate—or explore local eateries in Bowral.
Is this a group tour?
No, it’s a private tour, meaning only your group will participate, making for a more personalized experience.
What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans change.
This tour blends scenic beauty, delicious wines, and the comfort of private transport, making it a top pick for a day trip from Sydney. It’s perfect for those wanting a taste of Australia’s wine country without the hassle of organizing logistics themselves.