Sydney Wine Tasting and Southern Highlands Tour with Pick Up and Drop Off
A guided journey through award-winning cool-climate wineries just 1.5 hours from Sydney
This full-day Southern Highlands winery tour takes guests from Sydney's CBD into one of New South Wales' most celebrated cool-climate wine regions, visiting four distinct estates across rolling countryside. With door-to-door transfers and a knowledgeable guide throughout, the experience is designed to suit both devoted wine enthusiasts and those simply looking for a refined day out.
The Southern Highlands sits approximately 90 minutes south of Sydney, offering a markedly different landscape of open farmland, heritage villages, and boutique vineyards. The region's cooler temperatures and elevated terrain create ideal growing conditions for elegant, structured wines that have earned consistent recognition at national and international level.
Each winery on the itinerary brings a distinct character to the day, from grand Georgian homesteads to contemporary cellar doors set among landscaped gardens. Guests move between estates at a relaxed pace, with time to explore, taste, and engage with the stories behind each bottle.
Lunch is available at one of three estate restaurants or, alternatively, at a local pub or hotel in the township of Bowral. The return journey to Sydney offers a comfortable wind-down, with the guide at the wheel so guests can reflect on the day's discoveries without concern for the drive home.
Tour Highlights
Visit four acclaimed wineries across the Southern Highlands in a single guided day, including Centennial Vineyards, PepperGreen Estate, Bendooley Estate, and Artemis Winery.
Experience guided cellar door tastings of cool-climate varietals at each estate, with insight into the region's terroir and winemaking philosophy provided throughout.
Enjoy fully inclusive door-to-door transfers from Sydney's CBD, allowing guests to taste freely without any concern about driving or navigation.
Travel through scenic countryside landscapes, passing historic villages such as Bowral and Berrima, set amid the natural beauty of the New South Wales Southern Tablelands.
Explore boutique estate offerings including artisanal olive oils, local produce, and curated retail collections at cellar doors along the route.
Choose from multiple dining options for lunch, including estate restaurants with fine dining menus or classic pub meals in the heart of Bowral township.
A flexible format that suits couples, groups of friends, corporate outings, and special celebrations with a refined yet relaxed atmosphere throughout the day.
Tour Itinerary
Guests are collected from their hotel or a designated Sydney CBD pickup point. The drive south through the New South Wales countryside takes approximately 1.5 hours, offering a scenic introduction to the region before the first estate visit.
Set within the town of Bowral, Centennial Vineyards combines award-winning cool-climate wines with picturesque estate grounds and an acclaimed on-site restaurant. The cellar door offers structured tastings that highlight the estate's commitment to both tradition and innovation.
Located in the historic village of Berrima, PepperGreen Estate occupies beautifully restored grounds and features a stylish tasting room alongside a boutique shop offering estate-produced olive oils and local artisan goods. Lunch is available here for guests who prefer a refined estate dining setting.
Bendooley Estate is anchored by a restored Georgian homestead and encompasses an award-winning restaurant, the celebrated Book Barn, and the Berkelouw reception space amid landscaped gardens. Wine tastings here reflect estate-grown varietals and the property's reputation for exceptional country hospitality.
Artemis is a boutique producer focused on small-batch, sustainably cultivated wines crafted with close attention from vine to bottle. The estate's tasting experience offers guests an intimate look at artisan winemaking philosophy and the regional terroir that defines each vintage.
Guests are driven back to Sydney's CBD, a relaxed 1.5-hour journey that allows for conversation and reflection on the day. Drop-off is at the original pickup point or nominated hotel.
What Is Included and Excluded
Included
- Return door-to-door transfers from Sydney CBD
- Professional tour guide throughout the day
- Guided wine tastings at four Southern Highlands wineries
- Access to cellar doors at all four estates
- Scenic countryside touring through the Southern Highlands
Not Included
- Lunch and any meals during the tour
- Additional wine purchases at cellar doors
- Personal travel insurance
- Gratuities for the guide
Important Information
Ready to Explore the Southern Highlands?
Secure your place on this guided winery tour from Sydney and enjoy a full day of cool-climate tastings, scenic countryside, and seamless transfers through one of New South Wales' finest wine regions.
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