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

Country air, cool-climate wine, and kangaroos. This 10-hour private trip from Sydney combines historic Berrima, two distinctive estates, Fitzroy Falls, Bowral shopping, and a picnic at a private farm. I like the relaxed mix of food, scenery, and local stories, and I especially like that the day ends away from the usual sightseeing circuit. The main drawback is the price, $411.52 per person, with lunch extra.

I also like the personal nature of the outing. Your group travels privately, and guide Sam has earned praise for looking after people from pickup through drop-off, sharing Australian history on the road, and arranging a memorable farm picnic. The long day covers plenty of ground, so you should be ready for a full schedule rather than a slow winery afternoon.

Key points at a glance

• A private 10-hour day from Sydney: Your group has the vehicle and guide to itself, with pickup offered and an 8:00 am start.
• Berrima opens the day: Sandstone cottages and colonial-era stories give the tour a strong sense of place before the wine stops begin.
• Bendooley Estate pairs wine with regional food: Expect cool-climate tastings alongside a charcuterie board.
• Mount Ashby adds French-inspired country style: The estate combines wine, cuisine, antiques, art, stables, and broad paddock views.
• Fitzroy Falls brings a change of pace: A forest walk leads to a waterfall framed by cliffs and tall gum trees.
• Boscobel Farm finishes with kangaroos: A private picnic under open skies gives the day its most personal and memorable moment.

Why this Southern Highlands day works

The Southern Highlands is a good choice when you want a break from Sydney that feels rural without requiring several days away. The route moves through vineyards, farmland, forest, historic villages, and open pasture. That variety matters because the day never depends on wine alone.

I see this as a sightseeing tour with wine tastings, not simply a winery tour with a few photo stops. You get local architecture in Berrima, food and wine at the estates, a waterfall walk, shopping in Bowral, and a private farm visit. Each part offers a different reason to get out of the vehicle.

The private format is important. Only your group participates, so the day should feel more flexible and personal than a large coach outing. You are not being moved through every stop with a crowd, though the exact amount of free time at each location is not specified. The 10-hour duration gives the guide room to include several stops, but it also makes this a full day.

Sam is the guide named in the available feedback. His strengths appear to be attentive hosting, local storytelling, and keeping the day organized from beginning to end. One particularly useful detail is that the drive itself is part of the experience, with Australian history shared along the way rather than saved for formal stops.

Berrima brings colonial character before breakfast wine

Berrima is a fitting first stop. The village is known for sandstone buildings and colonial character, giving you an early look at the Southern Highlands beyond vineyards and country estates.

I like starting here because it slows the rhythm immediately. Instead of rushing straight to a tasting room, you get a village setting where early Australian stories are connected to buildings you can see. The stone cottages create a strong visual contrast with the rolling farmland that follows.

The available information does not specify how long you spend in Berrima or which buildings you enter. Plan to treat it as a village visit rather than a formal guided museum tour. If you enjoy architecture, history, and quiet streets, this part may be one of the day’s best openings. If your priority is maximizing tasting time, you may find the morning more spread out than expected.

The road from Berrima continues through pastoral country. That drive is not wasted time. It helps you see why this area feels separate from Sydney, with open paddocks and a slower rural setting replacing city traffic.

Bendooley Estate pairs wine with local produce

Bendooley Estate is the first major food and wine stop in the detailed route. Here, you taste cool-climate wines with a charcuterie board featuring regional produce.

This pairing gives the tasting more substance than a few small pours on their own. The charcuterie adds texture and a local food element, so you can think about the region as a producer of both wine and farm products. Snacks are included, and the cheese and wine tasting is part of the day’s food focus.

The estate is described as sitting among lakeside vines and manicured grounds. That setting makes Bendooley more than a counter where you sample wine. You have grounds to look over, vines nearby, and a polished country atmosphere that fits the luxury label.

Keep your expectations measured. The tour information does not name the wines, list the number of tastings, or promise a cellar tour. You should expect a tasting experience, not a technical wine course. If you want detailed vintage comparisons or a long winemaking presentation, ask for those specifics before booking.

I would also pay attention to the timing of this stop. The day includes another estate, lunch, a waterfall, Bowral, and the farm picnic. Bendooley is one part of a larger program, so the stop is likely designed to give you a pleasant taste of the region rather than occupy an entire afternoon.

Mount Ashby mixes wine with French-inspired country style

Mount Ashby Estate provides the day’s most design-conscious stop. The property is known for French-inspired cuisine, local wines, antiques, art, stables, and a homestead surrounded by paddocks.

The detailed schedule places lunch here after the Bendooley tasting. Lunch is not included in the price, so you should budget separately for your meal. That is the clearest cost issue on the tour. The price covers a private full-day outing, snacks, and wine tastings, but not the main midday meal.

I like the contrast between the two estates. Bendooley focuses on wine, regional produce, and lakeside grounds. Mount Ashby brings in the homestead, art, antiques, and equestrian touches. You get a stronger sense of a lived-in country property rather than visiting identical tasting rooms.

The French influence also gives Mount Ashby a different mood. It suggests a more refined meal setting, while the surrounding paddocks keep the visit grounded in the Southern Highlands. If you appreciate food presentation, country architecture, and rooms with character, this may be the most appealing estate stop.

The practical point is simple: do not assume lunch is covered because food appears throughout the tour. Snacks and tastings are included, but lunch is extra. The description does not state a fixed lunch menu or price, so ask about current choices if food planning matters to you.

Fitzroy Falls changes wine country for forest and water

After the estates, the scenery turns to bushland. A forest walk leads toward Fitzroy Falls, where cliffs drop into deep valleys among tall gum trees and cool air.

This is an important change of pace. Wine tastings and historic villages can make a day feel civilized and polished. The walk gives you a more direct connection with the bush, even if the visit is relatively short compared with a full hiking day.

The description calls it a forest walk to a striking waterfall. It does not give the walking distance, trail grade, or exact time on foot. If you have mobility concerns, ask the operator for current details before booking. Most people can participate, and service animals are allowed, but the word walk still matters.

The cooler forest setting may also be welcome after lunch and tastings. You get shade, cliffs, trees, and the sound or sight of falling water instead of another building or vineyard. I would bring sensible walking shoes and sun protection, even though the supplied details do not list a required dress code.

Fitzroy Falls is also one of the day’s strongest photo stops. The contrast between towering gums, forested cliffs, and open valleys gives you a very different view from the farmland earlier in the route.

Bowral rewards slow browsing

Bowral brings the trip back to town. Boutique shops and antique stores offer a slower kind of sightseeing, with an emphasis on local craftsmanship and browsing rather than a single major attraction.

This stop suits you if you enjoy looking rather than collecting a checklist of monuments. Small shops can reveal a place’s taste and character in ways a quick roadside photo cannot. You might find the pace restful after the formal timing of tastings and the walking stop.

The tour does not promise shopping vouchers, reserved appointments, or particular stores. Your experience will depend on what is open and how much time the group has. Since this is a private tour, you may be able to explain your shopping interests to Sam, but the exact flexibility is not guaranteed.

Bowral also helps balance the day for people in a mixed group. One person can enjoy antiques, another can browse boutique goods, and everyone can take a break from the vehicle. Still, if shopping is your main goal, a dedicated Bowral visit would give you more time than this combined tour.

Boscobel Farm is the day’s personal finale

The final stop is Boscobel Farm, a private sanctuary among forest and pasture. A picnic is set under wide country skies while wild kangaroos graze nearby.

This is the most distinctive part of the program. Plenty of tours can offer a village, a winery, or a waterfall. A private farm picnic with kangaroos gives the day a more intimate ending, especially after the busy sequence of scheduled stops.

The available feedback gives this stop particular weight. Sam specifically noted that kangaroos were out and about on the farm for one couple. That detail is useful because wildlife is never fully predictable. The setting offers a chance to see kangaroos, but you should not treat an animal sighting as a guaranteed performance.

The picnic is also a practical reason to check what is included. Snacks are listed as included, while lunch is not. The description says a picnic is set at Boscobel Farm, but it does not clearly state whether this picnic replaces lunch, forms part of the afternoon refreshments, or includes a complete meal. Ask the operator exactly what food is supplied so you can plan accordingly.

I like ending here rather than returning directly from a tasting room. The open farm setting gives the day room to breathe. It also explains why the experience feels more personal than a standard winery circuit. You are not simply being shown the Southern Highlands. You are being brought into a private place connected with the company’s own touring style.

What the $411.52 price really buys

At $411.52 per person, this is not a budget day trip. The value comes from the private vehicle and guide, the long 10-hour schedule, pickup, multiple destinations, wine tastings, snacks, and the private farm finale.

You are paying for access to a carefully arranged day rather than for one major admission ticket. The tour links places that would be awkward to combine independently in one day, especially from Sydney. The guide also handles the driving, timing, and transitions, which lets you taste wine without worrying about driving back.

The price makes more sense for couples, families, or friends who value privacy and want a guide focused only on their group. Group discounts may improve the cost for a larger party. You should still compare the total against a self-drive day, adding fuel, meals, tastings, parking, and the value of having someone else manage the route.

Lunch is the key extra expense. Since it is not included, add that cost before deciding if the package fits your budget. The wine tastings and snacks help, but they do not remove the need to plan for a proper midday meal.

Timing, comfort, and who should book

The 8:00 am start and 10-hour duration make this a serious day out. You will cover villages, estates, bushland, shops, and a farm, so comfortable clothing and shoes make sense. The schedule should suit you if you prefer variety and want to see several sides of the region in one outing.

I would choose this tour for:

• Couples wanting a private countryside escape from Sydney
• Small groups celebrating a special day
• Wine drinkers who also enjoy history, shopping, and nature
• People who prefer a guide and vehicle rather than self-driving
• Visitors who want a quieter rural setting and a chance to see kangaroos

I would think twice if you want a slow, specialist wine tour with long tastings at only one or two estates. I would also reconsider if you dislike early starts, full-day schedules, walking, or extra meal costs.

Pickup is offered, mobile tickets are available, and confirmation is received at booking. The experience is near public transportation, although the tour itself is designed around private pickup and driving. Most people can participate, and service animals are allowed.

Free cancellation is available if you cancel at least 24 hours before the start time. Changes or cancellations made inside that window are not accepted for a refund.

Should you book this Southern Highlands tour?

Book it if you want a polished private day that combines wine, country food, village history, a waterfall, shopping, and a farm picnic. The strongest reasons are the range of stops, Sam’s attentive guiding style, and the chance to end with kangaroos at Boscobel Farm rather than another tasting room.

Skip it if the $411.52 price feels high once lunch is added, or if you want to set your own pace at every stop. For the right group, though, the private format gives this full day a personal feel that a large bus tour cannot match.

FAQ

What time does the tour start?

The tour starts at 8:00 am.

How long does the experience last?

The tour lasts approximately 10 hours.

Is pickup available?

Yes, pickup is offered.

Is this a private tour?

Yes. Only your group participates in the activity.

What is included in the price?

Snacks and wine tastings are included. Pickup is offered, and group discounts may be available.

Is lunch included?

No. Lunch is not included in the stated price.

Which wineries or estates are visited?

The route includes Bendooley Estate and Mount Ashby Estate.

Does the tour visit Fitzroy Falls?

Yes. The day includes a forest walk leading to Fitzroy Falls.

Will the tour visit Bowral?

Yes. You have time in Bowral for boutique shopping and antique stores.

Can I cancel for a full refund?

Yes, if you cancel at least 24 hours before the experience starts. Cancellations made less than 24 hours in advance are not refunded.