A Day In The Vineyards || Luxury Private Winery Tour From Sydney

The appeal here is the mix: you can taste cool-climate wines, walk through a historic village and finish on a private farm where kangaroos may be grazing nearby. I like the contrast between Berrima’s sandstone buildings and the open farmland, and the chance to see the Southern Highlands without having to drive between stops yourself.

The main consideration is the price, $411.52 per person, with lunch excluded. The day lasts about 10 hours, so it suits you best if you want a full outing rather than a quick winery visit.

At a glance

• A private day out: Only your group participates, which gives the outing a more personal feel than a large coach tour.
• Berrima’s sandstone streets: The day begins in a village known for colonial-era buildings and a slower pace.
• Two winery stops: Bendooley Estate and Mount Ashby Estate bring different settings, from lakeside vines to a French-inspired homestead.
• A waterfall walk: Fitzroy Falls adds forest and cliff scenery between the countryside stops.
• A farm-side finish: Boscobel Farm offers a picnic setting among forest and pasture, with kangaroos sometimes visible nearby.
• Lunch costs extra: Wine tastings and snacks are included, but lunch is not.

A full day in the Southern Highlands

This is not a wine-only outing. The Southern Highlands day links vineyards with a historic village, a waterfall, small-town browsing and a rural farm stop. That variety is the real draw: you get several distinct sides of the region instead of spending the whole day at one cellar door.

The tour starts at 8:00 am and runs for about 10 hours. Pickup is offered, and the activity is private, so your group will not be combined with strangers. That can make the day easier to shape around your own pace, though the supplied details do not specify how much time is allocated at each stop.

The drive itself is part of the experience. Sam, a guide named by people who have taken the tour, has shared Australian history along the way. That kind of context can make the countryside feel less like a view through a window and more like a place with a story. You can expect a full day on the road, so this is a better fit for people who are happy to trade a slow morning at home for a varied day out.

Berrima’s sandstone streets set the tone

Berrima is the first taste of the region’s colonial character. Sandstone cottages and historic buildings give the village a distinct feel from Sydney, while the quieter streets offer a gentle start before the winery visits and waterfall walk.

I like that the day begins with a place rather than a tasting room. Berrima helps you settle into the Southern Highlands’ mix of history and rural calm. The information provided does not set out a guided walking tour or a specific amount of free time, so think of this as a visit to a village stop, not a deep historical tour.

If browsing old buildings and small-town streets is your kind of travel, this stop should add welcome variety. If you mainly want a full schedule of wine tastings, remember that Berrima takes up part of a day already packed with other stops.

Bendooley and Mount Ashby bring two wine-country moods

The tour includes tastings at Bendooley Estate, where cool-climate wines are served with a charcuterie board featuring regional produce. Its lakeside vines and manicured grounds give the stop a polished country-estate feel. The tasting is included, which makes this more than a quick photo stop, though the exact wines and tasting format are not specified.

Mount Ashby Estate offers a different character. It is a boutique vineyard with French-inspired cuisine, antiques, a homestead and wide paddocks. Lunch is described as part of the visit in the tour outline, but the price details clearly list lunch as not included. Budget separately, and check what food options are available before you set out.

That distinction matters at this price. Wine tastings and snacks are included, but you should not assume a full meal is covered. The two estates give you a good sense of the region’s food-and-wine appeal, yet the final cost will be higher if you buy lunch or additional drinks.

The order of the winery stops may vary in the tour description, so I would treat them as two planned highlights rather than count on a precise sequence. Either way, the contrast between lakeside vines and a homestead framed by paddocks gives the wine portion more visual variety than a string of similar cellar doors.

Fitzroy Falls brings forest air and a change of pace

Fitzroy Falls shifts the day from farm and vineyard views to forested cliffs and a deep valley. A forest walk leads to the waterfall, with towering gums and cooler air adding a welcome change after time in the vehicle and at the estates.

This stop is appealing even if wine is your main reason for booking. The natural scenery breaks up the day and gives you a chance to stretch your legs. The information does not specify the walk’s length, difficulty or exact viewpoint, so I would not plan on a strenuous hike or a particular amount of time there.

The practical point is to wear comfortable shoes suitable for walking. That is sensible for a forest path, though conditions and facilities are not detailed. If you prefer a day spent entirely at wineries, this stop may feel like a detour. For most people, it is a useful change of scene.

Bowral offers a slower hour among shops

Bowral brings a town stop after the countryside and waterfall. Boutique and antique shops are the draw, with a chance to browse local craftsmanship at your own pace. This is not presented as a formal shopping tour, so the pleasure is in having time to wander rather than being led from store to store.

I like the pause in rhythm. You can take a break from tastings and scenery, look through the shops that interest you and get a feel for the town. The exact free time is not stated, so keep expectations flexible. If you want a long antiques hunt, ask how much time is planned before booking.

Boscobel Farm ends the day in open country

The final stop is Boscobel Farm, a private sanctuary among forest and pasture. A picnic is set beneath wide country skies, and kangaroos may graze nearby. That combination of open space and wildlife gives the day a more personal finish than simply driving back after the last winery.

The picnic setting is part of the experience description, but lunch is not included in the price. Clarify what is provided for the picnic and plan to cover your own meal if needed. This is one of the most important details to settle before you book, since a countryside picnic sounds like lunch but the inclusions say otherwise.

Kangaroos are a possibility, not a guaranteed sighting. Still, the farm stop adds a distinctly rural note to a day that might otherwise be defined by wine and shopping. If you enjoy quiet outdoor settings more than formal attractions, it could be the most memorable part.

What the $411.52 price gets you

At $411.52 per person, this is a premium day trip. You are paying for a private experience, a long itinerary with several distinct stops, pickup offered, wine tastings and snacks. You also avoid having to navigate the drive yourself, which is meaningful when the day includes villages, estates, a waterfall and a farm.

The value depends on what you want from the day. If you would otherwise book a private driver and visit several of these places independently, the convenience may justify the cost. If your priority is simply tasting wine, a less varied or group-based option may be better value.

Keep the excluded lunch in mind, along with any purchases at the wineries or shops. The stated price is not an all-meals-included fare. With that understood, the itinerary offers a broad introduction to the region rather than a single-purpose wine tour.

Who should book this Southern Highlands day

I would consider this tour if you want a private day outside Sydney that combines wine, scenery and small-town stops. It is especially suited to couples, friends or families who like variety and are comfortable spending most of a day out. The private format also makes it a sensible choice for a group that values time together over joining a larger coach.

It is less ideal if you want a tightly scheduled wine education, a long hike, or a low-cost outing. The tour gives you a sampler of several places, but the supplied information does not promise lengthy visits, detailed winery talks or a specific walking distance.

The small number of available ratings is very positive, and Sam is singled out for attentive care and historical commentary during the drive. That is an encouraging sign, though it is not a guarantee of who will guide your particular departure. Service animals are allowed, and the tour notes that most people can participate. Confirmation is received at booking; free cancellation is available up to 24 hours before the start time.

Should you book it?

Book this tour if you want a comfortable, private introduction to the Southern Highlands and value the mix of Berrima, wineries, Fitzroy Falls, Bowral and a farm setting. The variety is its strength, and the guide’s reported care and local-history commentary add to the appeal.

Before paying, confirm the pickup details, the planned order and timing of stops, and what the farm picnic includes. Most of all, plan for lunch as an extra. With those points clear, this is a strong choice for a full countryside day from Sydney, especially if you would rather see several sides of the region than spend the day in one winery.

FAQ

How long is the tour?

The tour lasts approximately 10 hours.

What time does the tour start?

The listed start time is 8:00 am.

Is the tour private?

Yes. Only your group participates.

Is pickup offered?

Yes, pickup is offered. The specific pickup arrangements are not provided here.

Are wine tastings included?

Yes. Wine tastings are included.

Is lunch included in the price?

No. Lunch is not included. Snacks are listed as included.

Which places does the tour visit?

The day includes Berrima, Bendooley Estate, Mount Ashby Estate, Fitzroy Falls, Bowral and Boscobel Farm.

Can I bring a service animal?

Yes. Service animals are allowed.

What is the cancellation policy?

You can cancel at least 24 hours before the experience starts for a full refund. Changes or cancellations made less than 24 hours before the start time are not accepted for a refund.