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Discover the Southern Highlands with this private winery tour from Sydney, featuring scenic stops, wine tastings, and a peaceful farm picnic for true relaxation.

If you’re looking for a day filled with scenic beauty, delicious wines, and charming villages, this private winery tour in the Southern Highlands offers exactly that. While we haven’t personally hopped on this particular journey, reviews and detailed descriptions suggest it’s a well-organized, authentic experience perfect for those seeking a relaxed, culturally rich escape less than two hours from Sydney.
What we love most about this tour: first, the personal touch of a private group, which means more flexibility and intimacy. Second, the scenic stops like Fitzroy Falls and Bowral offer a wonderful mix of nature and town life. However, one consideration is that lunch isn’t included, so planning ahead for a meal is wise. This tour is ideal for wine lovers, curious explorers, and anyone wanting to combine gentle wilderness with gourmet tastes—perfect if you prefer a day out that’s both leisurely and enlightening.
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This tour acts as a window into the diverse charms of the Southern Highlands, a region often overlooked by travelers heading to Australia’s more famous sights. It’s a well-rounded blend of history, nature, and gastronomy, all within a cozy, manageable day that doesn’t require any prior experience or extensive planning.
What sets this experience apart is the careful curation of stops, each showcasing different facets of the region. From elegant vineyards to quaint villages, you’ll get a taste of Australia’s cool-climate wines, paired with regional snacks and a picnic that feels like a true escape from city life.

Your adventure begins at 8:00 AM in the historic village of Berrima. Known for its sandstone cottages and colonial architecture, this town sets a relaxed, old-world tone. We loved the way the town’s quiet charm made us feel like stepping back in time. It’s an ideal spot to start your day, offering a peaceful atmosphere before heading into the countryside.
Next, you’ll visit Bendooley Estate, a lakeside vineyard renowned for cool climate wines. Here, a tasting session awaits, complemented by a cheese and charcuterie platter made with regional produce—perfect for snacking and indulging in local flavors. Visitors often praise the quality of the wine and the setting, describing it as a real highlight. One reviewer noted, “The wines were incredible, and the setting among lakeside vines was picturesque.”
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Lunch is served at Mount Ashby Estate, a boutique vineyard with French-inspired decor and estate antiques. The setting is charming, with sweeping paddocks and a homestead that feels both elegant and welcoming. While lunch isn’t included in the tour price, it’s a highlight for many, offering a delicious meal in a relaxed, scenic atmosphere. Expect a menu inspired by French classics, paired with local wines, making it a memorable mid-day break.
In the afternoon, the group heads to Fitzroy Falls, where forested cliffs drop into lush valleys. The walk to the waterfall is easy but rewarding, with towering gum trees and cool air. Several reviews mention how stunning and peaceful this stop is, especially for nature lovers. One reviewer shared, “The forest walk leading to the waterfall was a real highlight—just stunning scenery and fresh air.”
Next, the tour continues to Bowral, a town known for its antique stores and boutique shops. Here, you’ll have some free time to explore at your own pace. Many travelers appreciate this stop for its unhurried vibe and craftsmanship, providing a nice contrast to the winery visits and natural sights.
The day concludes at Boscobel Farm, a private sanctuary among forest and pasture. You’ll enjoy a picnic under open skies, with wild kangaroos grazing nearby. This peaceful farm setting, described as a “hidden gem”, lets you unwind with a glass of wine and regional snacks. Reviewers highlight the calm beauty of this farm and the chance to connect with Australia’s rural charm.

The combination of stunning scenery, knowledgeable guides, and authentic regional tastes makes this tour truly special. Past guests rave about the friendly, well-organized experience, noting the guide’s ability to balance informative commentary with relaxed pacing.
The wine tastings are a major highlight, with many reviewers expressing surprise at the quality and variety of the local wines. Plus, the scenic stops at Fitzroy Falls and Bowral are perfect for photo opportunities and quiet reflection, adding a natural, unhurried rhythm to the day.
The picnic at Boscobel Farm is especially loved, offering a genuine taste of rural Australia and a chance to see kangaroos grazing in their natural habitat.

At $411.52 per person, this tour offers good value considering its full-day itinerary, private group setting, and inclusion of wine tastings and snacks. While lunch isn’t included, the flexibility allows you to choose a meal that suits your taste and budget. The 10-hour duration ensures you get a comprehensive experience without feeling rushed.
The tour includes pickup service, making logistics straightforward, especially for visitors unfamiliar with the area. It’s a private tour, which means your group won’t be mixed with strangers—a plus for those who prefer a more personalized experience.
The cancellation policy is flexible, offering full refunds if canceled at least 24 hours in advance—important for travelers with unpredictable plans.

From enthusiastic feedback, it’s clear that knowledgeable guides like Sam add a lot of value, making the experience engaging and informative. One reviewer said, “Sam looked after us so well,” emphasizing the personal care provided.
The stunning views especially stand out—whether it’s the tranquil lakeside vines, the lush waterfalls, or the quiet farm with kangaroos grazing nearby. Past travelers describe the day as “exquisite,” “flawlessly organized,” and “a must-do,” illustrating how well it delivers on expectations.

This experience suits wine enthusiasts, lovers of scenic landscapes, and those who enjoy relaxed, authentic local culture. It’s perfect if you want to escape Sydney’s hustle and explore a region known for its pastoral elegance, quiet villages, and striking natural beauty.
It also works well for small groups or couples seeking an intimate, educational, and picturesque day out. If you’re traveling with friends or family who appreciate good wine, peaceful nature, and charming towns, this tour ticks all those boxes.

This private winery tour offers a genuine taste of Australia’s Southern Highlands, blending beautiful scenery, local wines, and delightful villages into a well-paced, thoughtfully curated day. The small-group setting, knowledgeable guide, and diverse stops make it an excellent choice for travelers who value authenticity and comfort.
While it’s not a cheap day trip, the value is clear: you get a full day of scenic beauty, regional flavors, and tranquil moments that are difficult to find in larger, more commercial tours. It’s best suited for those who want a personalized experience with plenty of opportunity for relaxation and discovery, all within a manageable drive from Sydney.
If you’re seeking an escape into Australia’s quieter side, this tour offers a lovely blend of countryside charm, superb wines, and memorable vistas—an experience that’s both enriching and utterly enjoyable.
“The Southern Highlands Tour was fantastic! From pick-up to drop-off, Sam looked after us so well. We tasted some incredible wines and learned about…”

Is lunch included in this tour?
No, lunch is not included, but the tour includes wine tastings and snacks. You might find the options at Mount Ashby Estate delightful, and the flexibility allows you to choose your own meal afterward if preferred.
What is the duration of the tour?
The tour lasts approximately 10 hours, starting at 8:00 AM and returning in the evening, providing a full but comfortable day out.
Is this a private group experience?
Yes, this is a private tour, meaning only your group will participate, which offers a more personalized and relaxed atmosphere.
Are there any physical activity requirements?
The stops include walking around scenic areas like Fitzroy Falls and the villages. The walks are generally easy, suitable for most travelers with moderate mobility.
Can service animals participate?
Yes, service animals are allowed on this tour.
How do I cancel if needed?
You can cancel up to 24 hours in advance for a full refund, giving flexibility if your plans change.
Is transportation included?
Yes, pickup is offered, simplifying logistics and ensuring you start and end your day comfortably.
This tour is a thoughtfully designed way to enjoy the best of the Southern Highlands, making it an excellent choice for those craving an authentic, scenic, and flavorful escape close to Sydney.