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

The best part of this private Southern Highlands outing is its range. In one long day, you move from sandstone village streets to cool-climate wine country, a forest waterfall, antique shops, and a private farm where kangaroos may graze nearby. I like the small-group format and the way the day mixes wine, food, scenery, and local history instead of focusing on wineries alone.

I also like the personal touch from guide Sam, who looks after the day from pickup through drop-off and adds stories about Australia along the drive. The main drawback is the pace: 10 hours is a full day, and lunch is not included, so you should be ready for a long outing with several stops.

Key points at a glance

• Berrima’s sandstone village: Begin among colonial buildings and early Australian stories before the wine stops begin.
• Bendooley Estate tasting: Sample cool-climate wines with a charcuterie board made from regional produce.
• Mount Ashby Estate: See a boutique vineyard with French-inspired food, antiques, art, stables, and open paddocks.
• Fitzroy Falls walk: Add a forest setting and waterfall views to a day otherwise centered on food and wine.
• Bowral browsing: Spend time with boutique and antique shops rather than rushing from one tasting room to another.
• Boscobel Farm picnic: Finish at a private farm with snacks, wide skies, pasture, forest, and the chance to see wild kangaroos.

Why this Southern Highlands day works so well

Sydney makes a fine base for city sights, but the countryside south of town has a different rhythm. This tour takes you into the Southern Highlands, where farmland, vineyards, village streets, and eucalyptus forest replace traffic and tall buildings.

I like that the day is not built around wine alone. You get a taste of the region’s colonial past in Berrima, a walk at Fitzroy Falls, shopping time in Bowral, and a quiet farm visit at the end. That variety matters because a full day of tastings can become repetitive, while this plan gives you several reasons to stay interested.

The private setup is also useful. Your group is the only group on the activity, so the day can feel more relaxed than a large coach trip. You are not sorting out strangers, waiting for a big group to return, or listening to a guide speak to dozens of people at once.

The tradeoff is time. A 10-hour schedule beginning at 8:00 am asks for an early start and a full commitment. You will cover several places, but you should not expect long, unhurried visits at every stop.

Starting among sandstone buildings in Berrima

Berrima gives the morning a strong sense of place. Its sandstone cottages and colonial character offer a clear introduction to the Southern Highlands before the route heads through farmland and vineyards.

This is a good first stop because it gives you something to look at beyond tasting-room shelves. Early Australian stories are part of the setting, and the village provides a calm beginning before the day gathers speed.

You will likely appreciate the contrast between Berrima and the later estates. Berrima feels built and historic, while the winery stops open into paddocks, lakes, gardens, and broad country views. If you enjoy architecture, local stories, and old village streets, this may be one of the most rewarding parts of the morning.

The supplied schedule gives Berrima a prominent place, but it does not specify how long you stay there. Keep your expectations practical. This is a stop within a larger day, not a dedicated walking tour of the village.

Wine and regional produce at Bendooley Estate

Bendooley Estate brings together two of the day’s main pleasures: cool-climate wine and food. Your tasting is paired with a charcuterie board featuring regional produce, which gives the stop more substance than a quick sip at a counter.

Cool-climate wines can have a style distinct from the warmer wine areas many people associate with Australia. The appeal here is not simply the number of wines poured. It is the chance to connect the drink with the surrounding Southern Highlands setting and local food.

The estate is described as having lakeside vines and carefully maintained grounds. That makes it a pleasant place to slow down, take in the setting, and enjoy the tasting without treating it as a rushed checklist item.

Wine tastings are included in the price. You should still pace yourself, especially because the day continues through more food, walking, and stops. If you do not drink wine, the scenery and food still provide some value, but this activity clearly favors people who want wine to be a central part of their day.

Lunch plans at Mount Ashby Estate

Mount Ashby Estate shifts the mood again, with French-style cuisine, local wines, antiques, artwork, stables, and wide paddocks. It is a boutique vineyard with more than a tasting room, and its homestead setting gives the stop a polished country feel.

The important practical point is that lunch is not included. The schedule places lunch at Mount Ashby Estate, but the advertised inclusions list only snacks and wine tastings. Confirm the lunch arrangement and budget for your own meal before you go.

That extra cost may be worthwhile if you want a proper meal in an attractive setting. French-inspired food and local wine fit the estate’s character, and a sit-down break can help on a day that begins early and continues into the afternoon.

Still, the price should be judged with lunch separate. At $411.52 per person, this is not a budget day trip. You are paying for a private experience, guide service, pickup, a long route through several Southern Highlands locations, included tastings, and a more tailored pace. You are not paying for an all-inclusive food package.

Mount Ashby is likely to suit you if you enjoy country estates with visual details. Antiques, art, and stables give the place more personality than a plain vineyard visit. If you prefer a simple tasting with little time spent on architecture or décor, this stop may feel less essential.

A cooler change of scene at Fitzroy Falls

Fitzroy Falls provides the clearest break from the food and wine theme. A forest walk leads to a waterfall framed by tall gums, cliffs, and deep valleys. The air and setting should feel cooler and more open than the estates.

I like the balance this stop brings to the day. After tastings and lunch, a short walk gives you a chance to move, breathe, and see the Southern Highlands in a more natural state. The route is not only about farms shaped for visitors. It also includes bushland and a dramatic drop through forested cliffs.

The exact walking distance and trail difficulty are not provided, so you should not assume a long hike or a fully accessible route. The information says most people can participate, but anyone with specific mobility concerns should ask the operator for current trail details before booking.

Fitzroy Falls can also be weather-sensitive. The provided details do not promise a certain water flow or specify what happens if conditions change. Think of it as a scenic forest stop with waterfall views, rather than the sole reason to book the tour.

Browsing boutique shops and antiques in Bowral

Bowral adds a slower, more local afternoon stop. Boutique and antique shops give you time to browse at your own pace and see another side of the region’s character.

This part will suit you if you like independent shopping, old objects, and small-town streets more than formal sightseeing. It also breaks up the drive and lets you choose what interests you. You might find something connected to local craftsmanship, or you may simply enjoy wandering without a fixed attraction list.

The limitation is that shopping is personal. If you are not interested in boutiques or antiques, Bowral may feel less exciting than the waterfall or vineyards. The schedule does not identify particular shops or guarantee time for purchases, so do not plan the day around a specific store.

Still, I think Bowral is a smart inclusion. It gives you a chance to spend money locally, browse rather than rush, and experience the area as a living town rather than only as a collection of estates.

Ending at Boscobel Farm with kangaroos nearby

The final stop at Boscobel Farm is the most distinctive part of the day. This private sanctuary sits among forest and pasture, and a picnic is set beneath wide country skies. Wild kangaroos may be grazing nearby, which gives the ending a sense of place that a standard restaurant cannot provide.

Snacks are included, but the details of the picnic menu are not listed. If food matters greatly to you, ask what is provided and whether dietary needs can be handled before booking.

The farm also gives the day a gentler finish. You have already visited a village, tasted wine, eaten or arranged lunch, walked through forest, and browsed Bowral. Sitting outdoors with open views makes sense as a final pause rather than adding another formal attraction.

Kangaroo sightings are possible but not guaranteed. The setting is part of the appeal, and you should treat any wildlife encounter as a bonus. Do not expect a zoo-style animal experience or close contact. The value is in being outdoors in a private rural setting where wild animals may appear naturally.

This farm stop received especially warm praise in the available feedback, with the guide noting that kangaroos were out and about during one visit. That detail captures the tour’s strongest quality: the best moments come from the mix of planning and chance.

What the private guide adds to the day

Sam is named as the guide associated with the experience, and the strongest personal detail is the care given from pickup to drop-off. The guide also shares Australian history during the drive, which helps connect the stops instead of making each one feel separate.

That matters on a route with a lot of road time. You are not simply being transported between wineries. The drive becomes part of the experience when the guide explains the places you pass and gives context to the countryside.

A private group also gives you a better chance to ask questions. If you want more time with wine, more detail about local history, or practical advice in Bowral, you can raise it directly with your guide. The advertised details do not promise a fully flexible itinerary, so major changes should not be assumed, but the format is more personal than a large scheduled group.

The guide’s role is one reason the price may make sense for couples, families, or close friends who value comfort and attention. For a solo visitor or a pair focused mainly on low cost, the amount may be harder to justify.

Is $411.52 per person good value?

This is a premium day trip. At $411.52 per person, the cost is high compared with a basic shared bus excursion, but the comparison is not exact.

You receive a private activity for your group, pickup is offered, the day lasts about 10 hours, wine tastings are included, snacks are included, and the route covers several very different locations. You also avoid planning the long drive, choosing which estates to visit, and arranging the day’s sequence yourself.

Lunch is extra, and that should be part of your calculation. The price also does not mean every meal or purchase is covered. Boutique shopping, antiques, and any additional food are your responsibility.

I see the strongest value for people who would otherwise hire a private driver or spend a great deal of time organizing a Southern Highlands route. The experience combines transport, a guide, private access to the day, and a varied plan.

It is less compelling if your main goal is one winery with a long tasting, or if you want the cheapest possible way out of Sydney. In that case, a shared tour or self-drive plan may cost less, though it will not offer the same private format.

Who should book this outing?

I would suggest this tour for:

• Couples looking for a polished country day outside Sydney
• Friends who want wine, food, shopping, and scenery in one outing
• Visitors who prefer a private guide to a large scheduled group
• People interested in colonial buildings, rural estates, and Australian bushland
• Anyone who likes the chance of seeing kangaroos in a natural farm setting

You should think twice if you dislike early starts, long days, or moving between several stops. It may also disappoint if you want extensive hiking, a guaranteed wildlife encounter, or lunch fully included in the price.

Pickup is offered, the start time is 8:00 am, and confirmation arrives when you book. Most people can participate, service animals are allowed, and the tour operates near public transportation. Free cancellation is available if you cancel at least 24 hours before the start time. Changes or cancellations inside that window are not accepted for a refund.

Should you book the Southern Highlands winery tour?

Book it if you want a private, full-day introduction to the Southern Highlands rather than a single winery visit. The combination of Berrima, Bendooley Estate, Mount Ashby, Fitzroy Falls, Bowral, and Boscobel Farm gives you a broad taste of the area, with Sam’s guiding and the final kangaroo picnic adding a personal touch.

Skip it if $411.52 feels too high once lunch and shopping are added, or if you prefer to spend a whole day at one estate. For the right group, though, the private format and varied route make this a strong choice for seeing more of the countryside without managing the details yourself.

FAQ

Where does this Southern Highlands tour take place?

The experience begins from Sydney and visits locations in the Southern Highlands, including Berrima, Bendooley Estate, Mount Ashby Estate, Fitzroy Falls, Bowral, and Boscobel Farm.

How long does the tour last?

The tour lasts approximately 10 hours.

What time does the tour start?

The listed start time is 8:00 am.

Is pickup available?

Yes, pickup is offered.

Is this a private tour?

Yes. Only your group participates in the activity.

Are wine tastings included?

Yes, wine tastings are included.

Are snacks included?

Yes, snacks are included.

Is lunch included?

No. Lunch is not included in the price.

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 begins for a full refund. Cancellations or changes made less than 24 hours before the start time are not accepted for a refund.