From Sydney: Cool Climate Wineries, Historic Towns, Wildlife

When it comes to exploring New South Wales beyond Sydney’s bustling streets, this private luxury tour of the Southern Highlands offers a perfect blend of sophisticated wine tasting, historic charm, and scenic beauty. We haven’t personally gone on this exact tour, but based on detailed reviews and descriptions, it’s clear that this experience captures the region’s understated elegance and rural character.

What stands out most are the refined cool-climate wineries, the chance to wander through historic villages, and the unforgettable wildlife encounters — especially the possibility of sharing a picnic with kangaroos grazing nearby. We love that the day promises both luxury and authenticity with private tastings and storytelling about early colonial Australia.

The only potential downside? The 10-hour length might be a long day for those with tight schedules or limited mobility, but for most, it’s a well-paced, rewarding experience. This tour suits travelers who appreciate fine wine, history, scenic landscapes, and a touch of wildlife — ideal for those wanting a luxurious yet genuine taste of regional Australia.

Good To Know

• Private luxury experience with tailored tastings and guided insights
• Stunning scenery, from rolling farmland to dramatic escarpments and lakes
• Historic villages like Berrima and Bowral, bursting with early colonial character
• Cool-climate wineries such as Mount Ashby Estate and Bendooley Estate
• Wildlife encounters, including grazing kangaroos during a countryside picnic
• Flexible cancellation and payment options for peace of mind

You can check availability for your dates here:

Exploring the Southern Highlands: What the Tour Offers

This curated day trip is designed for those who want to enjoy the best of the Southern Highlands without the hassle of planning. It begins in the charming town of Berrima, a well-preserved colonial village with sandstone cottages, historic inns, and quiet streets that evoke Australia’s early days. It’s a perfect starting point for understanding the region’s deep-rooted history.

From Berrima, the journey takes you through pastoral landscapes, lush farmland, and open grazing country. The first highlight is Mount Ashby Estate, a relaxed vineyard estate that champions cool-climate wines and French-inspired cuisine. The estate’s elegant homestead, art-filled stables, and paddocks provide a picture-perfect backdrop for tasting sessions that showcase the region’s refined varietals.

The scenery then shifts at Fitzroy Falls, where forested escarpments plunge into deep valleys. This dramatic landscape offers a striking contrast to the gentle countryside, giving you an opportunity to breathe in fresh mountain air and admire sweeping views.

Next, you arrive at Bendooley Estate, famous for a beautifully curated wine and cheese tasting. The lakeside setting, manicured grounds, and impressive cellar door make it a favorite spot for both wine lovers and those seeking peaceful, picture-worthy moments.

In Bowral, time slows down. You’ll find boutique shops, antique stores, and cafes, perfect for wandering and soaking in the Highlands’ sophisticated, artisanal vibe. It’s a delightful contrast to the rural charm, offering a glimpse into local craftsmanship and slow-paced elegance.

Finally, the day wraps up at Boscobel Farm, a private sanctuary among forest and pasture. Here, a gourmet picnic with a charcuterie and cheese platter is laid out beneath a wide sky, with wild kangaroos grazing just nearby. It’s an authentic, memorable finale to a day filled with fine wine, history, and natural beauty.

Detailed Breakdown of the Itinerary

Starting in Berrima

Guests are picked up comfortably, with the private guide providing a friendly and knowledgeable introduction to the region’s colonial past. Berrima’s sandstone buildings, historic inns, and quiet streets are perfect for a gentle stroll, filled with stories of early settlers and convict history. The quiet charm of Berrima offers an authentic taste of early Australian life, far from touristy spots.

Mount Ashby Estate

Travelling from the village, you’ll enjoy scenic countryside views en route. Mount Ashby Estate impresses with its relaxed atmosphere and focus on cool-climate wines. As one reviewer notes, “the estate’s wines are elegantly crafted, and the French-inspired food makes for a sophisticated tasting.” The estate’s spacious, art-filled surroundings and paddocks make it a peaceful spot for wine lovers.

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Fitzroy Falls

A highlight for nature lovers, Fitzroy Falls offers dramatic views of forested escarpments and deep valleys. The walkways and lookouts are wheelchair accessible, and the sense of scale here is impressive. The change in landscape provides a refreshing break from vineyards and adds a layer of natural drama to the day.

Bendooley Estate

This estate is often praised for its curated cheese and wine tastings, set against lakeside vistas. The beautiful cellar door and manicured gardens make it a perfect spot to relax and indulge. Guests frequently comment on the high quality of the cheese boards paired with regional wines—“a taste of luxury in a tranquil setting,” one reviewer said.

Bowral

Here, the emphasis shifts slightly to local craftsmanship. The town’s boutique shops and antique stores are ideal for browsing souvenirs or enjoying a quiet coffee. The area has a quiet refinement, making it a lovely place to stretch your legs and soak in the Highlands’ understated elegance.

Boscobel Farm

The day ends at this private farm, where an outdoor picnic with a charcuterie and cheese platter awaits. Wild kangaroos grazing nearby add a touch of the wild Australian landscape. Reviewers note that “the setting is picture-perfect, with wide country skies and a peaceful ambiance,” making it an ideal conclusion to the day.

Why Choose This Tour? The Benefits and Practicalities

Comfort and Privacy: The entire experience is private, with a fully guided tour that ensures personalized attention. The vehicle is described as luxurious, making long drives comfortable.

Educational Value: Learn about the region’s colonial past, wine-making traditions, and landscape features, all explained by a guide whose stories add depth to the scenery.

Authentic Experiences: From historic villages to private tastings, this tour offers genuine moments that are often missed on larger group excursions.

Scenic and Wildlife Encounters: The combination of rolling farmland, escarpments, lakes, and native wildlife makes for memorable photos and a true sense of being in regional Australia.

Timing and Flexibility: The 10-hour duration might seem long but allows plenty of time to enjoy each stop without feeling rushed. Flexible cancellation and payment options add peace of mind, especially in uncertain travel times.

Value for Money: Given the high-quality private tastings, gourmet picnic, and personalized guide service, the experience offers good value—especially for those seeking a more refined, authentic day out.

Who Would Love This Tour?

This experience is perfect for wine enthusiasts, history buffs, and nature lovers alike. It appeals to travelers wanting a luxurious, private day that still feels authentic. If you’re after scenic views, regional charm, and wildlife encounters in a relaxed setting, this tour checks all those boxes. It’s especially suitable for those who prefer small-group or private experiences over crowded, cookie-cutter tours.

Final Thoughts

This private Southern Highlands tour offers a balanced mix of wine, history, and scenery with touches of wildlife and local craftsmanship. The focus on refined cool-climate wines and historic villages makes it stand out from more typical day trips, providing a genuine taste of regional Australia in comfort and style.

If you’re seeking a well-paced, intimate experience that combines luxury with authenticity, this tour provides a rewarding escape from Sydney’s busy streets. The stunning views, engaging storytelling, and the chance to share a picnic with kangaroos make it a memorable choice for those wanting to explore Australia’s scenic, historical heartland.

FAQ

What is the duration of this tour?
The tour lasts about 10 hours, making it a full-day experience that allows ample time at each stop.

Is this a private tour?
Yes, it’s designed for private groups, ensuring personalized attention and a tailored experience.

What are the main stops on the tour?
Stops include Berrima, Mount Ashby Estate, Fitzroy Falls, Bendooley Estate, Bowral, and Boscobel Farm for the picnic.

Are there tasting options included?
Yes, private tastings at refined wineries like Mount Ashby Estate and Bendooley Estate are part of the experience.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is there an opportunity to learn about the region’s history?
Absolutely, the guide shares stories of early colonial Australia and the region’s development.

What should I bring?
Comfortable clothing, camera, and curiosity—everything else, including the gourmet picnic, is provided.

Is this tour suitable for kids?
While primarily aimed at adults, the scenic and wildlife aspects could appeal to older children or teenagers.

Does the tour accommodate dietary restrictions?
This detail isn’t specified, but you might be able to request special arrangements when booking.

What makes this tour stand out from other day trips?
The combination of private tastings, scenic diversity, historic storytelling, and wildlife encounters creates a well-rounded, authentic experience.

In summary, this private Southern Highlands tour is ideal for those who value a blend of luxury, history, and natural beauty. Whether you’re a wine lover, a history enthusiast, or just after a peaceful countryside escape, it promises a day full of memorable moments and stunning vistas.

You can check availability for your dates here: More Great Tours Nearby