If you’re eyeing a day trip from Sydney that combines scenic beauty, exquisite wine, and a touch of countryside relaxation, this wine tour through the Southern Highlands promises just that. While I haven’t personally taken this exact trip, the detailed itinerary and glowing reviews paint a clear picture of a well-curated experience that balances comfort, authenticity, and a love for good wine.
What I love about this tour? First, the chance to visit some of New South Wales’ top cool-climate wineries, each with its unique character and award-winning wines. Second, the seamless transport and private guide mean you can focus on enjoying the day without the hassle of planning logistics or driving. The only potential downside? The tour’s duration means you’ll want to pace yourself—and perhaps skip heavy lunches to savor the wines fully.
This experience is ideal for couples seeking a romantic escape, groups of friends eager to taste local wines, or anyone wanting a relaxed yet refined day outside the city. It’s especially suited for those who value insider insights, beautiful vistas, and boutique wines in a friendly, intimate setting.
Key Points

- Convenient Pickup & Drop-off: Comfortably transported from Sydney’s CBD, with no worries about driving.
- Diverse Wineries: Visit five distinct wineries featuring award-winning cool-climate wines and historic estates.
- Flexible Lunch Options: Choose to dine at the wineries or explore Bowral’s local eateries.
- Expert Guidance & Private Vehicle: A dedicated guide enhances the experience, offering insights and making the day flow smoothly.
- Scenic Countryside: Enjoy panoramic views of rolling vineyards and charming villages.
- High Repeat Bookings & Positive Reviews: The tour’s reputation is stellar, with one reviewer calling it “excellent” and promising to do it again.
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Contents
- Key Points
- A Deep Dive Into the Tour Experience
- The Journey Begins: Comfortable Transport & Personalized Service
- Visiting Centennial Vineyards
- Peppergreen Estate in Berrima
- Bendooley Estate Book Barn
- Artemis Wines: Boutique & Personal
- Flexibility with Lunch
- Return to Sydney
- What the Price Reflects
- Why This Tour Works
- Who Should Book This Tour?
- FAQs
- Final Thoughts
- Our Top Picks in Sydney
- More Wine Tours in Sydney
- More Food & Drink Experiences in Sydney
- More Tour Reviews in Sydney
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A Deep Dive Into the Tour Experience

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The Journey Begins: Comfortable Transport & Personalized Service
Starting the tour with pickup from Sydney’s CBD sets a relaxed tone. The private vehicle ensures your group travels together comfortably, and with a dedicated guide, you’ll gain insights into the region’s history, wine scene, and local stories. The approximately 1.5-hour drive is scenic, giving you a preview of the lush countryside that awaits.
Visiting Centennial Vineyards
Your first stop, Centennial Vineyards in Bowral, is a standout. Known for its award-winning cool-climate wines, this estate offers a wonderful blend of picturesque landscapes and hospitable cellar doors. Here, you’ll enjoy about an hour of tastings, where the staff will pour and explain their best selections. As one reviewer noted, the wines are exceptional, and the hospitality makes the visit memorable.
The estate’s setting encourages relaxed conversations, and the panoramic views provide excellent photo opportunities. You’ll appreciate the chance to taste a variety of wines that showcase the region’s signature cool climate—think crisp whites and elegant reds.
Peppergreen Estate in Berrima
Next, the tour visits Peppergreen Estate, located in the historic village of Berrima. This winery offers a more refined atmosphere, blending premium wines with artisanal experiences and sophisticated dining options. Expect to spend about an hour here, tasting their top wines and possibly purchasing a bottle for later.
This stop is particularly appealing for those interested in artisanal production and elegant wine styles. The estate’s charm enhances the tasting experience, and the staff’s knowledge is evident.
Bendooley Estate Book Barn
A unique highlight is Bendooley Estate, renowned not only for its vineyard but also for its historic Georgian homestead and literary vibe. The estate’s restored architecture and award-winning restaurant make this a picturesque setting for a short visit. You’ll have an hour here, savoring world-class wines and perhaps browsing the book barn, which adds a cultural touch to your wine journey.
This stop combines scenic beauty with a touch of history, making it a favorite among those who appreciate both wine and architecture.
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Artemis Wines: Boutique & Personal
The next destination, Artemis Wines, is a boutique producer dedicated to small-batch wines. Known for their elegance and balance, Artemis embodies the craft ethos of the region. With only 45 minutes allocated, this tasting session gives you a chance to explore more nuanced, handcrafted wines and appreciate the dedication behind each bottle.
As a boutique producer, Artemis offers a more intimate tasting experience, letting you ask questions and truly connect with the winemakers’ passion.
Flexibility with Lunch
You’ll have about an hour to eat, with options to dine at Peppergreen Estate, Centennial Vineyards, or Bendooley Estate. Alternatively, Bowral’s town center is filled with pubs and cafes serving steaks, chicken dishes, and pizzas—ideal for a more casual or quicker refuel.
This flexible approach means you can tailor the meal to your preferences, whether you want a sit-down experience or a quick bite.
Return to Sydney
After a leisurely afternoon, the drive back to Sydney’s CBD takes about 1.5 hours. You can relax, soak in more scenery, or chat with your guide about all things wine and regional history. The consistent praise from past travelers reflects how smoothly the day wraps up, leaving you refreshed and satisfied.
What the Price Reflects

At about $283 per person, this tour offers a lot. The cost includes wine tastings at five different wineries, private guide, vehicle, and bottled water. Given the quality of wineries visited and the personalized service, this is a solid value—especially for those who want a curated, hassle-free experience. Notably, the tour doesn’t include lunch or wine bottles for takeaway, which allows flexibility for individual preferences or additional purchases.
Why This Tour Works

The consistent positive review, with the comment “Excellent tour – will do again,” hints at a well-organized itinerary with attentive guides and top-notch wineries. Visitors consistently praise the stunning views and excellent wine selections, making it clear that the experience hits the right notes.
The small group size and private guide mean you’ll get tailored insights, making the day feel personal rather than commercialized. The flexibility in dining and the variety of wineries—ranging from historic estates to boutique producers—offer a well-rounded taste of the region’s best.
Who Should Book This Tour?

This trip best suits wine lovers who appreciate boutique wineries and scenic countryside. It’s also ideal for those who prefer a guided, all-inclusive experience—no worries about transport or logistics—and want to enjoy exclusive access and insider insights. Couples, friends, and small groups seeking a special day outside the city will find this tour well worth the investment.
FAQs

What is included in the tour?
The tour includes wine tastings at all five wineries, a private guide, private vehicle, and bottled water. Lunch is not included, giving you flexibility in where and what you want to eat.
How long is the drive from Sydney?
The trip from Sydney’s CBD to the Southern Highlands takes approximately 1.5 hours each way, offering scenic views along the way.
Can I buy wine to take home?
While the tour includes tastings, wine bottles for home are not included. However, you can purchase bottles at each winery during your visit.
Is this a private tour?
Yes, this is a private experience for your group only, providing a more personalized and relaxed atmosphere.
What’s the best time to go?
The tour operates daily between 8:00 AM and 5:30 PM, year-round. The region is especially beautiful in spring and autumn when the scenery is at its best.
Are there options for lunch?
Yes, you can dine at the wineries or explore Bowral’s local cafes and pubs. The tour provides about an hour for lunch, so you can choose based on your preferences.
Is this suitable for all ages?
Most travelers are able to participate, but note that this is a wine tasting tour—best suited for adults comfortable with alcohol tastings.
What’s the cancellation policy?
You can cancel free of charge up to 24 hours in advance for a full refund. Cancellations less than 24 hours before the tour start are not refundable.
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
“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…”
Final Thoughts

If your idea of a perfect day outside Sydney involves scenic vineyards, boutique wines, and charming estates, this Southern Highlands wine tour offers a thoughtfully curated experience. It’s a chance to escape the city, enjoy excellent wines in exquisite settings, and learn from passionate locals—all in a relaxed, private environment.
For those with a curiosity about Australia’s cool-climate wines or simply looking to unwind in beautiful surroundings, this tour provides real value. The combination of stunning views, insider access, and seamless transport makes it a standout choice for a memorable day trip.
While it’s not for the budget traveler seeking a quick tasting, the quality and personalized touches justify the price. Just remember to pace yourself, savor each moment, and bring along your favorite camera and curiosity.
Enjoy your trip to the Southern Highlands — a delightful blend of scenery, wine, and genuine hospitality awaits.
































