From Sydney: Cool Climate Wineries, Historic Towns, Wildlife

Exploring the Southern Highlands beyond Sydney’s busy streets offers a refreshing escape into a landscape of rolling farmland, historic villages, and elegant wineries. This private luxury tour by THE AUS ADVENTURE CO promises a full day of tasting world-class wines, uncovering early colonial stories, and enjoying wild kangaroos grazing nearby.

While we haven’t taken this exact journey ourselves, the thorough itinerary and glowing reviews suggest it’s a wonderful experience for those craving authentic Aussie charm combined with refined indulgence.

What makes this tour appealing? First, it’s the chance to visit refined cool-climate wineries that produce distinctly Australian wines with a French twist. Second, the focus on historic towns and storytelling adds depth to a day that’s more than just sipping wine. That said, the full 10-hour length and multiple stops mean you’ll want to be prepared for a long, but very rewarding, day on the road.

This trip suits travelers who appreciate comfort, culture, and a touch of nature — ideal for those wanting an authentic, less touristy look at Australia’s inland beauty.

Key Points

• Authentic small-town charm in Berrima and Bowral.
• Exclusive private tastings at high-quality, cool-climate wineries.
• Stunning scenery from escarpments to lakeside vineyards.
• Wildlife encounters with kangaroos grazing nearby.
• Historic insights into early colonial Australia.
• Luxury, comfort, and flexibility with a private guide.

You can check availability for your dates here:

An In-depth Look at the Itinerary

Starting Point: Berrima’s Colonial Charm

The journey begins in Berrima, one of Australia’s best-preserved colonial villages. We loved the way its sandstone cottages, historic inns, and quiet streets evoke a bygone era. This town isn’t just picturesque; it’s packed with stories of early settlers, and wandering through its historic lanes gives you a real sense of Australia’s colonial roots. From the reviews, travelers describe Berrima as “a step back in time,” emphasizing its well-maintained architecture and authentic atmosphere.

Scenic Drive Through Pastoral Landscapes

From Berrima, the tour winds through grazing country and rolling farmland, offering gentle views of the countryside. It’s a relaxing way to set the tone for the day, and the guide’s commentary adds context about the region’s agricultural heritage. This part of the trip promises plenty of opportunities to snap photos of open paddocks, with the occasional glimpse of farm animals and quaint homesteads.

Mount Ashby Estate: Cool-Climate Wines and Art

Next, you arrive at Mount Ashby Estate, a relaxed vineyard known for its cool-climate wines—think elegant reds and crisp whites. The estate’s French-inspired cuisine and scenic setting make for a delightful tasting experience. Guests generally appreciate the less commercial, more personal atmosphere here, as one reviewer noted, “The private tasting felt special, like visiting friends’ wineries rather than a tourist stop.” You’ll also see their art collection and stables, adding to the estate’s charm.

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Dramatic Views at Fitzroy Falls

The landscape shifts dramatically at Fitzroy Falls, where forested escarpments plunge into deep valleys. The vantage points here are breathtaking — a stark contrast to the gentle vineyards. The walkways and lookout points are accessible and well-maintained, offering fantastic photo ops. Expect to enjoy the fresh, mountain air and the lush greenery. Many travelers find this a highlight, with one describing it as “a stunning reminder of nature’s grandeur.”

Bendooley Estate: Cheese, Wine, and Scenic Beauty

Next, the tour visits Bendooley Estate, home to one of the region’s most beautiful cellar doors. Here, a curated cheese and wine tasting takes place among lakeside vineyards and manicured gardens. The reviews praise the quality of the cheeses and the elegant setting, with many noting it’s “a perfect spot to relax and savor local flavors.” The estate’s picturesque grounds make it an ideal spot for photos or a peaceful break.

Bowral: Boutique Shopping and Historic Charm

In Bowral, you’ll find boutique shops, antique stores, and cafes, perfect for a leisurely stroll. The town’s quiet sophistication offers a glimpse of regional Australian craftsmanship and design. Visitors often comment on the relaxed pace and the opportunity to browse unique items, making this a nice complement to the winery visits.

The Grand Finale: Boscobel Farm Picnic with Wildlife

The day ends at Boscobel Farm, a private sanctuary amid forests and open pastures. Here, an elegant picnic is prepared, featuring a charcuterie and cheese platter, served beneath wide country skies. The highlight? Wild kangaroos grazing nearby as you enjoy your meal. Several reviews mention how special this setting is, with one noting, “It felt like having a private picnic in a wildlife documentary.” The chance to relax and soak in the rural landscape makes this a memorable conclusion.

What to Expect from the Experience

Private, Guided, and Comfortable

The tour runs privately with a guide who speaks English, ensuring a tailored experience. The vehicle is described as a luxury setting, offering comfort after a long day of sightseeing. The full 10 hours means plenty of time to explore without feeling rushed, but you should be prepared for a full day on the road.

Authentic and Rustic

Travelers should expect an rustic, immersive experience—this isn’t a polished city tour. The focus is on genuine stories, scenic beauty, and quality tastings. The guide’s knowledge about the region’s colonial past and wine-making adds layers to the experience.

Flexibility and Cancellation

Booking is flexible — you can reserve now and pay later, with full refunds available if canceled 24 hours in advance. This feature is handy if your plans change unexpectedly.

Who Would Love It?

This tour suits adventurous travelers who enjoy scenic drives, wine, and history. It’s perfect if you want a luxury experience that’s also intimate and authentic. Families, couples, or friends who appreciate a mix of cultural discovery and wildlife encounters will find this a well-balanced outing. But keep in mind the length—it’s a full-day affair.

The Value of This Tour

Considering the private tastings at acclaimed wineries, the scenic stops, and the exclusive picnic, the value lies in the personalized, high-quality experience. Unlike larger coach tours, this one offers a more intimate look at the region’s true character. The inclusion of wildlife, historic towns, and gourmet food makes it a well-rounded way to see a less-visited side of New South Wales.

The Sum Up

This private luxury tour of the Southern Highlands delivers a taste of Australia’s refined countryside, combining wine, history, and nature in a relaxed setting. It’s best suited for those who want to avoid the crowds, enjoy authentic experiences, and savor every moment of an elegant day out. With stunning views, engaging storytelling, and a peaceful rural atmosphere, this tour offers genuine value—and memories that linger long after your return to Sydney.

Whether you’re a wine lover, a history buff, or simply after a scenic escape, this experience promises a comfortable, immersive glimpse into one of Australia’s most charming regions.

FAQ

Is this tour suitable for all ages?
Yes, it’s suitable for most adults, especially those who enjoy wine, scenery, and historic towns. Keep in mind the full-day length and walking involved at some stops.

What is the duration of the tour?
The tour lasts approximately 10 hours, so it’s a full-day commitment, offering plenty of time for sightseeing and tastings.

Are the tastings at wineries private?
Yes, all tastings are private, allowing a more personalized and relaxed experience.

What should I bring?
Comfortable clothing and shoes for walking, a camera for photos, and a sense of curiosity. The guide will handle tastings and meals.

Can I cancel the booking?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible if your plans change.

Is the tour suitable for people with dietary restrictions?
The picnic features a charcuterie and cheese platter, so if you have specific dietary needs, it’s best to confirm in advance.

Is transportation included?
Yes, transportation is provided in a fully private, luxury vehicle, making for a comfortable ride between stops.

Will I learn about local history?
Absolutely, the guide shares stories about early colonial Australia, adding depth to your experience.

What makes the scenery special?
From lush escarpments at Fitzroy Falls to lakeside vineyards, the views are diverse and stunning, offering perfect photo opportunities.

Can I customize the experience?
Since it’s a private tour, you can discuss your interests with the guide, making it a more personalized day.

This tour offers a well-balanced, authentic look at the Southern Highlands that combines wine, history, and nature — perfect for those who want to experience Australia’s countryside in style.

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