THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a private day from Sydney exploring the Southern Highlands: historic Berrima, cool‑climate tastings at Mount Ashby and Bendooley, a walk to Fitzroy Falls, boutique Bowral shopping, and a picnic as kangaroos graze. This ten‑hour route blends wine, nature, and history.
Spend a private day from Sydney exploring the Southern Highlands: historic Berrima, cool‑climate tastings at Mount Ashby and Bendooley, a walk to Fitzroy Falls, boutique Bowral shopping, and a picnic as kangaroos graze. This ten‑hour route blends wine, nature, and history.
The day begins on a cool country road as Sydney’s skyline falls behind and the Southern Highlands open into rolling paddocks and vine rows. You step out at Berrima among weathered sandstone cottages and the hush of a town shaped by 19th-century settlers; the air smells of damp earth and cut grass. From there the tour moves between manicured vineyards and a lakeside estate where tasting rooms keep low voices and the clink of glasses.
Verified experiences and guided adventures in the surrounding area.
Operated by The Australian Adventure Company · Bowral, New South Wales
The day begins on a cool country road as Sydney’s skyline falls behind and the Southern Highlands open into rolling paddocks and vine rows. You step out at Berrima among weathered sandstone cottages and the hush of a town shaped by 19th-century settlers; the air smells of damp earth and cut grass. From there the tour moves between manicured vineyards and a lakeside estate where tasting rooms keep low voices and the clink of glasses.
Geology here is blunt and honest: sandstone plateaus, deep gullies carved into the Illawarra escarpment, and the Fitzroy Falls plunge—roughly an 80‑metre drop—where river and gravity argue loudly. The region’s cool-climate wines favour chardonnay and pinot noir; soils of clay and shale give the wines a lean, mineral frame. Cultural notes thread through the day — colonial architecture in Berrima, the Book Barn at Bendooley, and Bowral’s antique shops reflecting a quieter pace of life.
Practically, expect about a 10‑hour private loop from Sydney with short guided walks (uneven boardwalks and lookouts) and multiple tasting sessions. Wear comfortable shoes for a short forest stroll at the falls, bring sun protection and a light layer for variable highland breezes. Hydrate between tastings and ask hosts about pour sizes if driving later.
This experience balances slow, sensory tasting with pockets of wilderness: vineyards that invite conversation and a final picnic at Boscobel Farm where kangaroos graze and evening light eases the day to a gentle close.
easy.
10 hours.
Suitable for most fitness levels; includes short easy walks and mostly seated tasting periods
The private tour runs about 10 hours and typically departs from an agreed pickup point in Sydney; confirm exact pickup when booking.
Tastings at included estates are part of the itinerary and light snacks or a charcuterie are served; lunch at Mount Ashby is included per the tour description.
Walking is limited—short, mostly easy walks to lookouts and the Fitzroy Falls viewing area; suitable for most abilities.
Yes—kangaroos and wallabies are commonly seen in paddocks and at Boscobel Farm; birdlife including kookaburras and rosellas is frequent.
Berrima dates to the 1830s as a planned colonial village on the Old Hume Highway and retains many sandstone buildings from that era.
Much of the area sits near Morton National Park where fire management and invasive species control are active priorities; visitors are asked to stick to paths and pack out waste.
The Australian Adventure Company operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The day begins on a cool country road as Sydney’s skyline falls behind and the Southern Highlands open into rolling paddocks and vine rows. You step out at Berrima among weathered sandstone cottages and the hush of a town shaped by 19th-century settlers; the air smells of damp earth and cut grass. From there the tour moves between manicured vineyards and a lakeside estate where tasting rooms keep low voices and the clink of glasses.
The day begins on a cool country road as Sydney’s skyline falls behind and the Southern Highlands open into rolling paddocks and vine rows. You step out at Berrima among weathered sandstone cottages and the hush of a town shaped by 19th-century settlers; the air smells of damp earth and cut grass. From there the tour moves between manicured vineyards and a lakeside estate where tasting rooms keep low voices and the clink of glasses.
Geology here is blunt and honest: sandstone plateaus, deep gullies carved into the Illawarra escarpment, and the Fitzroy Falls plunge—roughly an 80‑metre drop—where river and gravity argue loudly. The region’s cool-climate wines favour chardonnay and pinot noir; soils of clay and shale give the wines a lean, mineral frame. Cultural notes thread through the day — colonial architecture in Berrima, the Book Barn at Bendooley, and Bowral’s antique shops reflecting a quieter pace of life.
Practically, expect about a 10‑hour private loop from Sydney with short guided walks (uneven boardwalks and lookouts) and multiple tasting sessions. Wear comfortable shoes for a short forest stroll at the falls, bring sun protection and a light layer for variable highland breezes. Hydrate between tastings and ask hosts about pour sizes if driving later.
This experience balances slow, sensory tasting with pockets of wilderness: vineyards that invite conversation and a final picnic at Boscobel Farm where kangaroos graze and evening light eases the day to a gentle close.