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

Southern Highlands charm arrives early on this private day from Sydney: sandstone Berrima, cool-climate vineyards, Fitzroy Falls and a quiet farm where kangaroos may graze near your picnic. It is a full 10-hour outing, but the changing scenery keeps the day from feeling like one long wine stop.

I like the mix of food, wine and small-town character, rather than a tour built only around tastings. I also like the private format and the personal service associated with guide Sam, who has been praised for looking after people from pickup through drop-off and for adding Australian history during the drive. The main drawback is cost: at $411.52 per person, this is a serious day-trip purchase, and lunch is not included.

Key points at a glance

• Berrima begins the day with sandstone cottages and colonial-era character, giving you more than a quick winery visit.
• Bendooley Estate combines cool-climate wine with a regional charcuterie board, while its lakeside vines and manicured grounds add a polished country setting.
• Mount Ashby Estate brings French-inspired style, local wine, antiques and open paddocks, with lunch arranged there at your own expense.
• Fitzroy Falls adds a real bushland break, with a forest walk to a waterfall framed by tall gums and steep valley country.
• Boscobel Farm provides the most personal finish, with a private country setting, picnic atmosphere and the chance to see wild kangaroos.
• The tour is private, begins at 8:00 am and lasts about 10 hours, so it suits people who value flexibility and a slower day outside Sydney.

Why this Southern Highlands day works

Sydney has no shortage of organized day trips, but many keep you close to the city or funnel you through a predictable set of stops. This one heads south into a cooler, quieter part of New South Wales, where vineyards, grazing country, historic villages and bushland share the same day.

That variety is the real selling point. You are not simply tasting wine in one estate for hours. You move from Berrima’s old buildings to vineyard grounds, then to a waterfall, shops in Bowral and a private farm. Each stop changes the pace.

I would choose this for a special occasion, a small group of friends or a couple wanting a private day without managing a rental car. It also makes sense if you have already seen Sydney’s main sights and want an outing with more local flavor. The private setup means only your group participates, which is a major advantage for anyone who dislikes large coach tours.

The tradeoff is the long day and premium price. At $411.52 per person, you are paying for private transport, planning, a full day of stops and personal attention, not just the wine. That can be good value for a group that wants convenience, but harder to justify if your main goal is simply a tasting or two.

8:00 am departure and a guide-led drive south

The day starts at 8:00 am, with pickup offered. Exact pickup arrangements should be checked when booking, but the early start is sensible. You have several stops ahead, and a late departure would make the program feel rushed.

Sam is the named guide associated with the experience. The strongest praise attached to the tour focuses on his care from pickup to drop-off and the way he brings Australian history into the drive. That matters on a day like this because the roads between stops are part of the experience. A good guide turns the transfer time into context rather than dead space.

You should expect a full day in the vehicle, broken up by walks, tastings, lunch, shopping and the farm visit. Most people can participate, and service animals are allowed. The tour is near public transportation, though the private pickup remains the practical way to join it.

Berrima, where the day gets its historic footing

Berrima is an excellent first stop because it gives the outing a sense of place before wine enters the picture. The village is known for sandstone buildings, colonial character and early Australian stories. Its scale encourages a gentle start rather than a rapid-fire sightseeing routine.

Look for the texture of the old stone buildings and the compact village feel. This is the sort of stop where you can slow down, take photographs and listen to the history rather than chase a major attraction.

Berrima also helps explain the character of the Southern Highlands. The area is not only about vineyards and pretty paddocks. Its appeal comes from the meeting of old settlements, working farmland, cool-climate produce and bushland.

Do not expect a large town packed with attractions. The pleasure is in the atmosphere and the chance to begin the day at an easy pace. If you prefer famous landmarks and constant activity, this may feel quiet. If you like old villages with room to wander, it is a strong opening.

Bendooley Estate for wine and regional produce

The tasting at Bendooley Estate brings the first substantial food and wine stop. You taste cool-climate wines with a charcuterie board featuring regional produce, a pairing that makes the visit more satisfying than sampling wine alone.

Cool-climate wines can have a style distinct from the fuller, warmer-climate bottles many people associate with Australia. You do not need specialist knowledge to enjoy the tasting, but it is worth paying attention to how the wines work with the cured meats and other regional items on the board.

The setting adds to the experience. Bendooley is described through its lakeside vines and manicured grounds, so this is a polished country stop rather than a bare cellar door. You get the visual pleasure of vineyards and designed gardens along with the tasting.

This is one of the tour’s best choices for anyone who enjoys a refined setting but does not want the whole day to feel formal. You can appreciate the estate, sample local wine and eat something substantial before the next stop.

The included features list confirms wine tastings and snacks, but lunch is specifically not included. Since the day includes a lunch stop later, do not assume every meal or dish is covered in the tour price. If you have dietary needs, ask the operator in advance rather than relying on the general description of regional produce.

Mount Ashby Estate and the question of lunch

Mount Ashby Estate shifts the mood toward French-inspired country style. The estate is known for French-style cuisine, local wines, antiques, art and stables, with broad paddocks around the homestead.

This is a particularly appealing stop if you enjoy buildings and furnishings as much as the wine. The art and antiques give the property a lived-in, collected feel, while the stables and open farmland keep it connected to rural life.

Lunch follows at Mount Ashby, but it is not included in the $411.52 price. That detail deserves attention when you budget. A day with wine tastings, transport and a private guide can already feel expensive, and an additional restaurant bill will add to the total.

Still, paying separately gives you a little more control. You can choose from what is available rather than being locked into a fixed meal included in the package. The supplied information does not list the exact lunch menu or cost, so ask before departure if the meal is important to your budget or dietary plans.

The visit also gives you a chance to pause. By this point, you have had a village stop and a tasting, so a proper lunch in a vineyard setting is useful before the afternoon’s walk and shopping.

Fitzroy Falls brings cool forest air

The afternoon changes direction at Fitzroy Falls. Instead of more cellar doors, you take a forest walk toward a waterfall, with towering gum trees, steep forested cliffs and deep valley views.

This is the physical highlight of the day. The walk provides fresh air and movement after the morning drive and tastings. You get a clearer sense of the Southern Highlands as bush country, not just farmland with vineyards.

The information supplied does not give the walk’s length, difficulty or exact viewing platform. Plan for a forest walk rather than a strenuous hike, but ask the operator if you need precise details. Most people can participate, though anyone with mobility concerns should confirm the walking conditions before booking.

Weather will shape this stop. In cool or wet conditions, the forest may feel especially atmospheric, while slippery paths or poor visibility could reduce the view. Comfortable walking shoes and a light weather layer are sensible choices, even though the tour description does not specify a dress code.

Fitzroy Falls is also a good balance to the estate visits. Wine country can become repetitive if every stop involves a tasting room. Here, the reward is the sound and sight of falling water, tall gums and open valley space.

Bowral for a slower hour of browsing

Bowral offers a different sort of attraction. The town is known for boutique and antique stores, giving you time to browse rather than follow a strict sightseeing route.

I like this stop because it lets you choose your own pace. You might look for local craftwork, browse old furniture and objects, or simply enjoy the town’s country shopping streets. The description does not promise a particular shop or fixed shopping allowance, so think of Bowral as unhurried free time rather than a guided retail program.

This is useful after the waterfall walk. The day alternates between hosted experiences and moments where you can look around on your own. That rhythm makes the private tour feel less tightly managed.

The drawback is that shopping appeal is personal. If antiques and boutiques are not your thing, Bowral may feel less important than the wine estates or Fitzroy Falls. For people who enjoy browsing, though, it adds local character and supports the sense that you are visiting a region rather than checking off a list of attractions.

Boscobel Farm and the kangaroo finish

The final stop at Boscobel Farm is what gives the day its most distinctive ending. This private sanctuary sits among forest and pasture, with a picnic arranged under wide country skies. Wild kangaroos may be grazing nearby.

That possibility is important. The kangaroos are not presented as a guaranteed wildlife show, and you should treat any sighting as a bonus. The farm setting is still worthwhile without them, but seeing animals moving through the pasture would give the day a memorable Australian finish.

The private nature of Boscobel also separates it from a standard public attraction. You end the day in a quieter setting, away from the formal estate grounds and town streets. It is a chance to sit, eat snacks or picnic food as arranged, and take in the countryside without another scheduled tasting.

There is some ambiguity around food here. Snacks are included, and the overall description refers to a picnic, but lunch is listed as not included. I would confirm exactly what is supplied for the farm picnic and what you need to purchase yourself.

This final stop was important enough to earn direct praise in the available feedback, especially when kangaroos were out and about. That tells you where the tour’s emotional payoff may come from: not a grand attraction, but a calm private setting and a little luck with wildlife.

What the price includes, and what it does not

The listed price is $411.52 per person. The package includes snacks and wine tastings, and pickup is offered. Because this is a private activity, the cost also buys exclusivity for your group rather than placing you with strangers.

That can be worthwhile if you are traveling with friends or family and want a day shaped around your interests. You avoid the usual large-group compromises, and Sam can give more direct attention to your group. The value is weaker for a solo visitor or budget-conscious couple who would be happy with a less personal group excursion.

Lunch is not included. This is the key extra cost to plan for. The exact amount is not provided, so you should ask before booking if the final budget matters.

The current rating is 5 from three published ratings, a very positive signal but a small sample. The praise centers on organization, attentive care, wine, local history, the countryside and the kangaroos at Boscobel. I would take that as evidence of a well-regarded personal service, not as a guarantee that every day will have identical weather, wildlife or timing.

Who should book this private day

I would recommend the tour to you if several of these points fit:

• You want a full day outside Sydney without driving.
• You prefer a private vehicle and guide to a large group.
• You enjoy wine but also want history, scenery and small-town stops.
• You like gentle walks rather than a day spent only at estates.
• You are comfortable paying extra for convenience and personal service.
• You are visiting with friends or family and can share the private-tour value.

I would think twice if you want a low-cost tasting, a tightly scheduled sightseeing day or a guaranteed wildlife encounter. The program has a relaxed country rhythm, and some of its best moments depend on weather, personal taste and whether kangaroos happen to be visible.

Free cancellation is available if you cancel at least 24 hours before the 8:00 am start. Changes or cancellations made inside that window are not accepted for a refund, so keep the local cut-off time in mind.

Should you book the Southern Highlands tour?

Book this tour if you want the Southern Highlands in several different moods: historic Berrima, vineyards and local wine, French-inspired estate style, Fitzroy Falls, Bowral shops and a private farm finish. The mix is more rewarding than a winery-only outing, and Sam’s attentive guiding appears to be a central part of the experience.

The strongest reason to choose it is the private format paired with the Boscobel Farm visit. The strongest reason to hesitate is the price, especially once you add lunch.

For a milestone day, a small group or anyone wanting a polished countryside escape from Sydney, I think the tour earns consideration. For strict budgets, compare the cost against the value of private transport and guide time before booking. If that convenience matters to you, this is a well-shaped day with enough variety to justify the long hours.

FAQ

Where does the tour take place?

The tour starts from Sydney and explores the Southern Highlands of New South Wales, including Berrima, Bendooley Estate, Mount Ashby Estate, Fitzroy Falls, Bowral and Boscobel Farm.

What time does the tour start?

The stated start time is 8:00 am.

How long does the experience last?

The tour lasts approximately 10 hours.

Is pickup available?

Yes. Pickup is offered, though you should confirm the exact pickup arrangements when booking.

Is this a private tour?

Yes. Only your group participates in the private activity.

Is lunch included?

No. Lunch is not included in the tour price.

What food and drink are included?

Snacks and wine tastings are included. The tour also includes a charcuterie tasting at Bendooley Estate, while lunch is listed separately as not included.

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