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

The best part of this private Southern Highlands day is its variety. You move from sandstone village streets to vineyard paddocks, forested cliffs, antique shops and a quiet farm picnic, all in one long outing from Sydney. The final stop at Boscobel Farm, with kangaroos grazing nearby, gives the day a personal country feel that a standard winery bus trip cannot easily match.

I like the mix of wine and regional food, especially the cool-climate tastings with local produce and charcuterie. I also like the way Sam, the guide, adds Australian history during the drive rather than leaving you to make sense of the countryside on your own.

The main drawback is the 10-hour schedule. You cover a lot of ground, and lunch is not included in the $411.52 price, so this is best for people who enjoy a full day out rather than a slow, single-estate wine visit.

Key points at a glance

• Berrima’s sandstone village: Begin among colonial buildings and early Australian stories before heading into the countryside.
• Mount Ashby Estate lunch stop: See a French-inspired vineyard setting, antiques, art and broad paddock views, with lunch purchased separately.
• Bendooley wine and cheese tasting: Sample cool-climate wines with a charcuterie board featuring regional produce.
• Fitzroy Falls walk: Add a forest stop and a waterfall framed by towering gum trees and steep valley country.
• Boscobel Farm picnic: Finish at a private farm sanctuary, where kangaroos may be grazing as you eat.
• Private transport and guiding: Your group travels together, with pickup offered and no unrelated passengers sharing the activity.

Why this Southern Highlands day works

This is not just a winery transfer. It is a broad introduction to the Southern Highlands, a region where village history, farming, wine, bushland and small-town shopping sit close together. You get several different moods without having to arrange separate transport between them.

The day begins at 8:00 am and lasts about 10 hours. That early start matters. Sydney is the base, but the experience is designed around the countryside beyond the city, so you need enough daylight for Berrima, the estates, Fitzroy Falls, Bowral and Boscobel Farm.

Because the activity is private, the day has more flexibility than a large group excursion. You are not sharing the vehicle with strangers, and the group discount may make the price easier to justify if several people book together. Pickup is offered, and confirmation arrives when you book.

The supplied price is $411.52 per person. That is a serious day-trip budget, especially since lunch is extra. Still, the value is not limited to the wine tasting. You are paying for a full private itinerary, transport, guiding, several major stops and a picnic setting that would be awkward to reach without your own vehicle.

Berrima starts the day with sandstone and stories

Berrima gives the morning a strong sense of place. Its sandstone cottages and colonial character make it more than a quick coffee stop, and the early Australian stories shared during the drive help put the village in context.

I like beginning here because it eases you into the Southern Highlands. You are not rushed straight into a cellar door. Instead, you start among old buildings and quiet village streets, then watch the scenery change as the road runs through rolling farmland.

The stop is also a good fit if you want more than food and wine. The tour includes history as well as scenery, and Sam is praised for looking after the group from pickup through drop-off and for sharing Australian history along the way.

Berrima is not presented as a long guided history lesson, so you should not book this expecting hours inside museums or heritage sites. Its value is in the setting, the short stories and the change of pace from Sydney.

Mount Ashby brings French style to the paddocks

Mount Ashby Estate adds a polished but rural note. The property is known for French-style cuisine, local wines, antiques, art and stables, with sweeping paddocks around the homestead.

Lunch is associated with this stop, but it is not included in the tour price. That distinction is easy to miss when planning your budget. Allow extra money for the meal, and check the arrangements at booking if lunch is an important part of your day.

The estate works well for people who enjoy places with visual character. You can expect more than rows of vines. The homestead, artwork, antiques and open farm views give the stop a sense of country living, while the French influence adds a different flavor from a basic cellar-door visit.

The drawback is time. With several other stops still ahead, Mount Ashby is one part of a packed day, not a full afternoon devoted to a single estate. If you want long tastings, a leisurely meal and plenty of time to browse one property, a dedicated winery tour may suit you better.

Bendooley pairs cool-climate wine with local produce

Bendooley Estate is the food and wine center of the day. Here you taste cool-climate wines with a charcuterie board built around regional produce, making the tasting feel more substantial than a few small pours on their own.

The setting is described as lakeside vines with carefully maintained grounds. That gives you a pleasant place to pause, look across the property and connect the wine with the climate and farming country around you.

The schedule places Bendooley and Mount Ashby close together, though the supplied tour details describe the order slightly differently in different sections. What matters for planning is that both estates are part of the same full-day route, and you should expect wine tastings plus a separate lunch expense.

Wine tastings are included, as are snacks. If you do not drink alcohol, the rest of the day still has plenty to offer, but wine is an important part of the experience rather than a minor extra. Ask the provider ahead of time about alternatives if that matters to your group.

Fitzroy Falls changes the pace

After the estates, the scenery turns from open farmland to forest and steep valley country. Fitzroy Falls brings a welcome change from tasting rooms and dining tables, with a forest walk leading toward a striking waterfall.

The setting includes towering gum trees, cool air and forested cliffs dropping into deep valleys. It is the kind of stop that helps the day feel like a Southern Highlands outing rather than a chain of winery appointments.

The walk is described as a forest walk, but the available information does not give its exact distance, surface or difficulty. Most people can participate in the overall activity, yet anyone concerned about walking should ask the provider for current details before booking.

I like this middle-to-late stop because it breaks up the food and wine. You get a chance to stretch your legs and see a more rugged side of the region. The tradeoff is that a waterfall stop depends on the day’s timing, so you should not expect an extended bushwalking session.

Bowral is for an unhurried browse

Bowral gives the afternoon a slower town rhythm. Boutique and antique stores offer a chance to browse local craftsmanship, household pieces and small finds rather than simply taking another scenic photograph.

This stop suits you if you enjoy wandering without a strict sightseeing checklist. It also adds a human scale to the day. After estates and bushland, Bowral shows how the Southern Highlands feels as a lived-in regional center.

Shopping time can be one of the most personal parts of a private tour, since different people want different things. Some in your group may enjoy antiques, while others may prefer boutiques or a short rest. The tour description does not promise specific shops or guaranteed purchases, so treat Bowral as an opportunity to explore rather than a fixed shopping program.

Boscobel Farm ends the day in open country

The final stop at Boscobel Farm is the most distinctive part of the route. This private sanctuary sits among forest and pasture, and a picnic is arranged under wide country skies while wild kangaroos may graze nearby.

That setting gives the day an ending with real Australian character. You are not finishing at another commercial tasting room. You are sitting on a private farm, looking across pasture and woodland, with the chance to see native wildlife in a natural country setting.

The picnic is also an important value point. Snacks are included, but the supplied details do not clearly state every item served at the final picnic. If you need a full meal after the estates, remember that lunch is not included and confirm how the picnic fits into the day’s food arrangements.

Kangaroos are wildlife, not a scheduled performance. You may see them, and the supplied feedback specifically highlights the pleasure of finding them out and about on the farm, but sightings cannot be guaranteed. That uncertainty is part of what makes the stop feel less staged.

What the private format changes

A private tour is most useful here because the route includes several different interests. One person may want wine, another may care about history, and someone else may be happiest at Fitzroy Falls or Bowral’s shops. A private group can share the same day without being locked into the priorities of a large coach group.

Sam’s role also seems central to the experience. The strongest praise focuses on his care from pickup to drop-off, his history stories during the drive and the smooth handling of the day. That is useful information when comparing this with a self-guided rental car outing. You are not only buying a vehicle and a route. You are getting someone to connect the stops.

The tradeoff is cost. At $411.52 each, a private tour can be expensive for one or two people. Group discounts may help, and the fixed price becomes easier to assess when you count the length of the day, the pickup option, wine tastings, snacks and the number of included stops.

You also need to accept the pace. Berrima, two estates, Fitzroy Falls, Bowral and Boscobel Farm make for a generous program. You will see more places than you would on a single-estate visit, but you may have less time at each one.

Food, wine and what you should budget

Wine tastings and snacks are included. A charcuterie board with regional produce is part of the Bendooley experience, giving you something to eat alongside the wine.

Lunch is not included. This is the clearest extra cost to plan for, especially because the day begins early and runs into the evening. The tour description connects lunch with Mount Ashby Estate, but it does not provide a set menu or price.

If your group has dietary needs, ask before departure. The supplied information confirms snacks, tastings and regional produce, but it does not list vegetarian, vegan, gluten-free or other specific options.

The food is valuable because it ties the route to the region. You are not only looking at vineyards. You are tasting local wine and produce in places where the estates, farms and countryside are part of the same story.

Who should book this day

I would recommend this tour to couples, families and small groups who want a private day beyond Sydney without planning every turn themselves. It is particularly good for people who want a mix of wine, village history, nature, shopping and wildlife rather than one narrow theme.

It also suits first-time visitors who want a broad look at the Southern Highlands. Sam’s historical commentary can help you understand what you are seeing, while the private format keeps the day more personal.

You may want another option if you prefer a slow, serious wine program. This route gives wine real attention, but it also includes a waterfall, village stops, shopping and a farm picnic. It is a sightseeing day with wine, not a focused wine masterclass.

The same applies if you dislike early starts or long days in a vehicle. The 8:00 am departure and approximately 10-hour duration are firm clues about the pace. You should be comfortable spending much of the day on the road between stops.

Practical details before you reserve

Pickup is offered, and the tour starts at 8:00 am. It is a mobile-ticket activity, and confirmation is received at booking.

The activity is private, so only your group participates. Group discounts are available, which can improve the value for friends or family booking together.

Service animals are allowed, and the activity is near public transportation. Most people can participate, though the exact Fitzroy Falls walking conditions are not supplied, so ask if mobility is a concern.

Free cancellation is available when you cancel at least 24 hours before the local start time. Cancellations or changes made less than 24 hours before departure are not accepted for a refund.

Should you book A Day in the Vineyards?

Book it if you want a wide-ranging Southern Highlands day with private transport, local wine, regional food, country scenery and a genuine chance to see kangaroos at a private farm. The Boscobel picnic, Fitzroy Falls and Sam’s personal guiding help separate it from a basic cellar-door transfer.

Think twice if your priority is low cost, a short outing or several hours at one winery. Lunch costs extra, the day is long and the route covers a lot of ground.

For a group willing to share the cost, this is an appealing way to see parts of southern New South Wales that are easy to miss from Sydney. Just budget for lunch, accept the full schedule and treat the kangaroos as a lucky part of the farm setting rather than a promise.

FAQ

Where does the tour start?

The experience begins from Sydney, with pickup offered. The stated start time is 8:00 am.

How long does the tour last?

The tour lasts approximately 10 hours.

Is this a private tour?

Yes. Only your group participates in the activity.

What places are included?

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

Are wine tastings included?

Yes. Wine tastings are included, along with snacks.

Is lunch included in the price?

No. Lunch is not included, so you should budget separately for it.

Can I cancel for a full refund?

Yes, if you cancel at least 24 hours before the experience start time. Cancellations or changes made less than 24 hours before departure are not accepted for a refund.