This private tour of the Southern Highlands promises a full day of stunning scenery, exceptional wines, and authentic regional charm—all tailored for those who appreciate good taste and a leisurely pace. Whether you’re a wine enthusiast or just eager to escape Sydney’s hustle, this experience offers a blend of culture, nature, and gourmet delights that’s hard to beat.
What makes this tour appealing? First, the knowledgeable guides who seem to bring the region’s stories and flavors to life. Second, the variety of stops—from charming villages to breathtaking waterfalls—ensuring there’s always something beautiful around the corner. One potential consideration is the price—at over $400 per person, it’s an investment, but for many, the quality and exclusivity make it worthwhile. This tour suits visitors looking for a balanced day of sightseeing and tasting, especially those who enjoy private, curated experiences rather than just group outings.
Key Points

Premium private experience tailored for small groups or individuals
Stunning scenery including waterfalls, rolling farmland, and lakeside vineyards
In-depth wine tastings with regional and French-inspired wines and local cheese
Authentic regional charm in Berrima, Bowral, and Mount Ashby Estate
Leisurely pace with plenty of time for wandering, tasting, and enjoying the landscape
Value for money given the personalized service, expert guides, and multiple memorable stops
The Itinerary in Detail

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Starting in Berrima: Historic Charm and Colonial Character
Your day begins early at 8:00am in the historic village of Berrima. Known for its sandstone buildings and colonial architecture, Berrima sets a relaxed tone that invites you into a slower, more charming pace of life. You’ll notice the cobblestone streets and old-world pubs, providing a peaceful backdrop before heading into the vineyards. It’s a perfect introduction that hints at the region’s blend of history and elegance.
Bendooley Estate: Lakeside Vines and Gourmet Tastings
Next, you’ll visit Bendooley Estate, where the focus is on wine and cheese. Here, you’ll enjoy tastings of cool climate wines—the region’s signature—and pair them with a selection of regional cheeses. The estate’s manicured grounds and lakeside vines make for a picturesque setting, ideal for a relaxed tasting experience. Guests have praised the way the guide engages with the group, sharing insights about the wines and regional produce, which adds depth to the experience.
Mount Ashby Estate: French-Inspired Charm and Paddock Views
Lunch is served at Mount Ashby Estate, a boutique vineyard with a French twist. The estate is decorated with antiques and framed by sweeping paddocks—something that catches the eye and elevates the culinary experience. The French-style cuisine, paired with local wines, offers a taste of regional sophistication. The setting encourages downtime, conversation, and savoring each bite amid beautiful surroundings.
Fitzroy Falls: Nature’s Spectacle
In the afternoon, the tour takes you to Fitzroy Falls. Here, the scenery shifts dramatically to forested cliffs and deep valleys. The walk to the waterfall is an easy trek, but it rewards you with views of ancient trees and the sound of rushing water. One reviewer highlighted this stop as a “striking waterfall surrounded by towering gums,” which emphasizes the natural beauty of this part of the trip. It’s the perfect moment to breathe deeply and appreciate the wilderness.
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Bowral: Boutique Shopping and Craftsmanship
Next, the group visits Bowral, a charming town renowned for its boutique stores and antique shops. Here, unhurried wandering through local shops gives a glimpse into regional craftsmanship and design. Many travelers enjoy the chance to browse and pick up souvenirs, making this stop both relaxing and culturally enriching.
Boscobel Farm: A Private Sanctuary and Picnic
The day concludes at Boscobel Farm, a private property that feels like a true sanctuary. Surrounded by forests and pastures, it’s the perfect spot for a picnic under the wide country sky. You might even spot kangaroos grazing nearby, a delightful touch of Australian wilderness. Guests have raved about the tranquil setting, calling it “a picnic among wilds” that caps off a day of natural beauty and culinary indulgence.
The Experience: Comfort, Convenience, and Authenticity

Transportation and Group Size
The tour is private, meaning only your group participates, which enhances comfort and flexibility. Starting at 8:00am, the day lasts roughly 10 hours, allowing plenty of time at each stop without feeling rushed. Pickup is offered, making the start easy, and the small group dynamic is ideal for sharing conversations and learning from your guide. The cost of $411.52 per person might seem steep, but given the private setting, expert guide, tastings, and scenic stops, many find it provides excellent value.
Quality of Service and Guides
Reviews repeatedly mention Sam, the guide, as attentive and knowledgeable. One reviewer said, “Sam looked after us so well,” highlighting how personalized attention makes this experience special. The guide’s insights into the region’s history, wine making, and natural environment enrich the journey, transforming it from a simple tour into an educational, memorable experience.
Tasting and Food
While lunch is not included, the opportunity to sample regional wines and cheeses makes up for it. The tasting stops are thoughtfully chosen to showcase the region’s cool climate wines, which many travelers find to be a highlight. The picnic at Boscobel Farm, with its fresh country air and grazing kangaroos, offers a genuine taste of rural Australia—a moment many reviews describe as “exquisite” and “flawlessly organized.”
Scenic Highlights
The scenery is a major selling point. From rolling farmland and lakeside vineyards to forest-clad waterfalls, every stop offers photogenic views that you won’t forget. Reviewers have noted the stunning waterfalls and beautiful landscapes, confirming that the experience provides ample opportunities for memorable photos and quiet reflection.
Who Will Love This Tour?
This experience is perfect for wine lovers who want more than just a tasting; it’s great for those who appreciate history, scenery, and gourmet food in a private, relaxed setting. It’s also ideal if you prefer small groups and personalized attention over large bus tours. The itinerary suits travelers seeking a balanced day—not packed with too many stops, but enough to keep the day engaging and varied.
The Sum Up: The Value and Appeal

For travelers craving a luxurious yet authentic day exploring the Southern Highlands, this private winery tour offers a compelling mix of scenic beauty, regional flavors, and personalized service. The carefully curated stops, from historic villages to waterfalls and lakeside vineyards, ensure each moment feels special. The guide’s local knowledge and the intimate setting turn what could be a standard day trip into a memorable journey through Australia’s charming countryside.
While the price is on the higher side, the exclusive nature, quality tastings, and scenic stops justify the cost for many. If you’re after a day that combines relaxation, education, and delicious tastes in a beautiful landscape, this tour is an excellent choice. Perfect for couples, friends, or anyone wanting a peaceful yet engaging escape from Sydney—this day is about enjoying the region’s best without the crowds.
FAQ

Is this tour suitable for children or families?
The tour is designed for adults and is private, so it might suit families with older children, especially those interested in wine and nature. However, check with the provider for specific age restrictions.
What’s included in the price?
You’ll receive snacks and wine tastings at selected stops, but lunch is not included, giving you the flexibility to choose or bring your own if preferred.
How long is the tour?
The experience lasts approximately 10 hours, starting at 8:00am and ending in the late afternoon or early evening.
Is transportation provided?
Yes, pickup is offered, and the tour is designed to be a private, comfortable journey.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour start time.
Are service animals allowed?
Yes, service animals are permitted on the tour.
Is this tour accessible using public transport?
While the tour includes pickup, the experience is most convenient if you’re able to be collected from your accommodation or a nearby location, as public transport options within the region may be limited.
What should I wear?
Comfortable clothing suitable for walking and weather conditions. Layers are recommended, especially for nature stops.
Is there a limit on group size?
Since this is a private tour, only your group participates, providing a more personal and flexible experience.
Are the wineries and stops family-friendly?
Yes, the stops are scenic and casual, making them suitable for guests of all ages, though wine tastings are geared towards adults.
This private Southern Highlands winery tour offers a well-rounded day of scenic beauty, regional flavors, and intimate experiences—perfect for those wanting a taste of Australia’s countryside at its best.
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