From Sydney: Cool Climate Wineries, Historic Towns, Wildlife

Exploring the Southern Highlands: A Luxurious Day of Wine, History, and Nature

If you’re seeking an escape from the hustle of Sydney, this private tour through the Southern Highlands offers a blend of fine wine, historic towns, and wildlife in a relaxing luxury setting. From carefully curated vineyard visits to wandering through colonial-era villages, this experience promises a thoughtful mix of culture and scenery.

What truly makes this tour stand out are the refined cool-climate wineries, the scenic drive through rolling pastures and forested escarpments, and the chance to relax with an exclusive picnic on a private farm. Plus, the personalized nature of a private guide ensures you get a tailored, immersive experience—perfect for those looking for understated elegance and authentic local stories.

One consideration to keep in mind is that this experience involves rustic and immersive elements, which means comfort and expectations should align with a more natural, countryside vibe. It’s best suited for travelers who enjoy a relaxed pace, good conversation, and the quiet charm of historic towns.

This tour works beautifully for wine lovers, history buffs, and anyone craving a scenic day away from Sydney’s tourist crowds. It’s a well-balanced mix of education, landscape, and luxury, with genuine opportunities to connect with Australia’s colonial past and its wildlife.

Key Points

• Exclusive private experience with a knowledgeable guide
• Visit to refined cool-climate wineries with private tastings
• Historic villages and colonial architecture rich with stories
• Scenic landscapes including mountains, farmland, and waterfalls
• Gourmet picnic on a private farm with kangaroos nearby
• Ideal for wine enthusiasts and history lovers seeking authentic experiences

You can check availability for your dates here:

A Full Breakdown of the Southern Highlands Private Tour

Starting in Berrima: Colonial Charm and Historic Tales

Your day begins in Berrima, often considered one of Australia’s best-preserved colonial villages. Here, sandstone cottages and historic inns set a timeless scene, walking through quiet streets that seem untouched by modern hustle. Reviewers highlight the area’s well-preserved architecture and the stories hidden in each corner, making it a compelling start for history enthusiasts.

Berrima’s charm isn’t just visual; guides share stories about early colonial life, giving you a sense of the region’s foundation. The quiet atmosphere, combined with the chance to snap photos of historic buildings, makes this part of the trip both relaxing and educational.

Rolling Farmland and Mount Ashby Estate

Next, you’ll venture through pastoral landscapes—vast green paddocks dotted with grazing sheep and cattle. The drive itself offers plenty of viewing opportunities to appreciate the gently undulating countryside.

The highlight here is Mount Ashby Estate, known for its cool-climate wines and French-inspired cuisine. The estate boasts an elegant homestead surrounded by art-filled stables and paddocks that stretch to the horizon. This vineyard emphasizes relaxed sophistication, and guests enjoy private tastings of wines that are notable for their finesse and unique regional character. Reviewers mention that the estate’s atmosphere is refined yet welcoming, with some describing the wines as “surprisingly complex,” especially given their approachable style.

Fitzroy Falls: Nature’s Dramatic Show

The landscape then shifts dramatically at Fitzroy Falls, where forested escarpments plunge into deep valleys. This stop offers breathtaking views and is a favorite for nature lovers. The forest scenery and waterfalls provide a striking contrast to the gentle countryside, and many guests comment on how picturesque and peaceful this part of the tour is.

Expect a leisurely walk and plenty of photo opportunities—it’s a chance to appreciate the natural beauty that surrounds this region. The sense of scale and the sound of rushing water make it a truly immersive experience, especially for those who love capturing nature’s grandeur.

More Great Tours Nearby

Bendooley Estate and Cheese Tasting

Arriving at Bendooley Estate, you’ll indulge in a curated cheese and wine tasting among lakeside vineyards and manicured gardens. The estate’s beautiful cellar door is considered one of the most picturesque in the region, with many reviewers noting its charming ambiance and delicious pairings.

Guests often appreciate the opportunity to sample a variety of local cheeses paired with regional wines, making this a sensory highlight. The estate’s peaceful setting and well-maintained grounds make it perfect for a relaxed tasting experience, with some reviews mentioning it as a highlight for food and wine aficionados.

Bowral: A Town of Craftsmanship and Boutique Charm

In Bowral, you’ll have free time to explore boutique shops, antique stores, and cafes. The town exudes a quiet sophistication, and visitors often comment on its artisanal stores and historical architecture. It’s a perfect place to soak in the Highlands’ understated elegance and perhaps pick up a unique souvenir.

The Final Stop: Private Farm Picnic

The tour concludes at Boscobel Farm, a private property surrounded by forests and pastures. Here, you’ll enjoy a gourmet picnic featuring a charcuterie and cheese platter. Guests love the experience of dining outdoors beneath wide, open skies while wild kangaroos graze nearby—an authentic wildlife encounter that adds to the day’s charm.

Reviewers describe the picnic as “serene” and “delightful,” with many appreciating the personalized setup and the chance to relax after a full day of sightseeing. The farm’s peaceful environment offers a perfect ending to a day of indulgence and exploration.

What to Expect: Practical Details and Tips

Duration and Comfort

This is a 10-hour private tour, with most of the day spent smoothly traveling between sites in a luxury vehicle. The private nature means you can customize the pace and focus, making it ideal for those who prefer a relaxed, tailored experience rather than a crowded group tour.

Guide and Language

Guided by an English-speaking expert, your guide will provide insights into each location’s history, wine, and landscape. Past guests have praised the guides for their friendly demeanor and depth of knowledge, making the journey both informative and enjoyable.

Price and Value

While the tour isn’t inexpensive, the all-inclusive private setup, gourmet experiences, and exclusive access justify the cost. You’ll enjoy private tastings, a gourmet picnic, and personalized attention—elements that elevate this beyond a typical day trip.

Additional Considerations

• The experience is described as rustic and immersive, so a sense of adventure and appreciation for natural settings will enhance your enjoyment.
• It’s designed for those wanting to avoid tourist traps and experience authentic regional charm.
• The flexibility of book now, pay later and full refund options** provides peace of mind in planning.

Who Will Love This Tour?

This experience is perfect for wine lovers who appreciate private tastings and scenic settings, as well as history buffs interested in colonial stories. It offers a great balance of relaxation, education, and scenery—ideal for couples, small groups, or anyone who values personalized service and authentic cultural encounters.

If you’re after a luxury, immersive day that combines Australia’s natural beauty with its winemaking heritage, this tour hits the mark. It’s especially suited for travelers looking to escape Sydney’s busy tourist scene and dive into the quiet elegance of the Highlands.

The Sum Up

This private tour through the Southern Highlands offers a well-rounded experience that combines delicious cool-climate wines, historic towns, stunning landscapes, and wildlife encounters. The attention to detail, from private tastings to a gourmet picnic on a private farm, makes it a particularly appealing choice for those seeking a personalized, refined day out.

The scenic stops at Fitzroy Falls and Bowral, along with the stories shared about early colonial life, add layers of cultural and natural richness. The seamless blend of relaxation, education, and scenery ensures that you’ll leave feeling both inspired and rejuvenated.

For anyone craving an authentic taste of Australia’s pastoral beauty, this trip delivers a memorable slice of the Highlands’ understated charm. It’s a day crafted for wine enthusiasts, history lovers, or anyone looking for a quiet, scenic escape with a touch of luxury.

FAQ

Is this tour suitable for children or families?
Since the experience is quite immersive and involves scenic walks and outdoor picnicking, it’s best suited for adults or older children comfortable with walking and outdoor environments.

How long does the tour last?
The full experience takes approximately 10 hours, including travel, tastings, and stops. It’s a full-day adventure but designed to be comfortably paced.

Are the tastings private?
Yes, all tastings are private, allowing for a more personalized experience. You won’t be part of a large group, which enhances the intimacy and focus.

Can I cancel if my plans change?
Absolutely. You can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans shift.

Is there a dress code?
Casual and comfortable clothing is recommended, especially for walking around historic villages and natural sites. A hat and sunscreen are advisable for outdoor stops.

What languages are available for the guide?
Guides speak English, and the experience is designed for English-speaking guests. No other language options are specified.

In essence, this tour offers a thoughtful, elegant way to experience the Southern Highlands’ best—perfect for those who want to combine wine, history, and nature into one memorable day.

You can check availability for your dates here: