Cool-climate wine with countryside breathing room. This private day trip threads together historic Berrima lanes, cellar door tastings, and a proper nature break at Fitzroy Falls, so you do not feel like you are racing from stop to stop. I also like that your schedule is built around standout places like Mount Ashby Estate and Bendooley Estate, with time for slow, scenic pacing and tastings. One thing to consider is that lunch is not included, so you will want to budget for that meal when you arrive at Mount Ashby.

The best part for me is the mix of flavors and scenery: charcuterie-style tasting bites and cool-climate wines in the vineyards, then a calm picnic finish at Boscobel Farm. I also like the care factor highlighted in the reviews, especially when the host (Sam) manages pickup and keeps the day moving smoothly while sharing context on the drive. If you want only wineries and nothing else, the waterfall walk and Bowral wandering may feel like more sightseeing than you expected.

Key things I’d plan around

• A private, just-your-group format for a more relaxed pace
• Berrima + Bowral for village atmosphere and old-stone charm
• Two tasting-focused vineyard stops with local food pairings
• Fitzroy Falls for cool air and a real walking break
• Boscobel Farm picnic with countryside views and kangaroos nearby

Price and logistics: what $411.52 buys you

At $411.52 per person for about 10 hours, this is not a budget shuffle day. Instead, you are paying for a private route, winery time, and built-in food-and-drink moments like snacks and wine tastings.

That private format matters in the Southern Highlands. You get fewer bottlenecks, a day that can feel tailored to your pace, and a route that strings together different moods, from colonial village streets to cellar-door tasting rooms to a waterfall walk. It is also worth noting there are group discounts, which can make the math easier if you are sharing with friends.

The one real planning note is that lunch is not included. The day still includes a lunch stop at Mount Ashby Estate, but you should expect to pay for your own meal there. If you like to travel with fewer surprises, you might decide in advance what kind of lunch you want to have and roughly what you will spend.

Morning start from Sydney: timing that avoids the worst driving

You begin at 8:00 am, with pickup offered. Starting early is a practical choice here, because it gives you more daylight for the vineyard stops and still leaves room for an afternoon walk at Fitzroy Falls.

A mobile ticket is handy for a day like this, especially when you are bouncing between multiple estates. And since the day is near public transportation, it is a safer bet if you need an alternate way in or out, but the main expectation is pickup.

Private tours like this also tend to be smoother when everyone shows up on time. If you are staying in Sydney, I would treat the morning like you would a museum ticket, arrive early enough to avoid stress.

Berrima first: sandstone charm and a calmer start

The day kicks off in Berrima, a village known for sandstone cottages and colonial-era character. This is more than a scenic warmup. It sets the tone for the Southern Highlands, which is all about pastoral calm and old architecture rather than big-city noise.

Why I like this start: it is early enough that you can appreciate the place before your afternoon turns into tastings and farm-country walking. Also, Berrima is the kind of town where a short wander feels satisfying even if you are not a hardcore shopper.

Expect the pace to be gently paced, with time to orient yourself and settle in before heading toward the wine and countryside portion of the day.

Bendooley Estate: cheese and cool-climate wine tastings by the vines

Next up is Bendooley Estate, a vineyard stop that pairs wine with food, including a cheese and wine tasting. The setting is described as lakeside vines and manicured grounds, which is a good reminder to slow down when you arrive.

Cool-climate wine regions have a different rhythm than warmer-climate areas. You are often tasting styles that feel crisp and structured, and pairing them with cheese helps you notice the small differences between varieties and blends.

Practical tip for this part of the day: treat the tasting like a menu. You do not have to like everything, but tasting with food makes it easier to understand what a producer is aiming for. If you are deciding what to buy later, it is smart to pay attention while you still feel fresh, because by mid-afternoon your taste memory can get muddled.

This is also a good mental reset before lunch, because it gives you that vineyard-view moment without a long hiking stretch.

Mount Ashby Estate: French-style dining, antiques, and paddock views

Lunch happens at Mount Ashby Estate, described as having French-style cuisine, local wines, and a homestead framed by art and stables. There is also an antiques angle, so you get a bit of a country estate vibe, not just a tasting room feel.

Since lunch is not included, you have to choose your approach. I recommend going into lunch hungry but also open-minded, because estate dining often means you can order something that matches the day’s wine theme. If you want to keep it simple, you can focus on a main meal and save your energy for the next part of the itinerary.

The antiques and estate atmosphere are a quiet bonus. If you enjoy design details and old objects with a sense of place, this is the stop where you can take your time. If you are only there for wine, you can still enjoy the setting, but you may want to be direct about what you want so you do not lose time.

Fitzroy Falls: the waterfall walk when you need fresh air

After lunch, the route turns toward Fitzroy Falls, where you get a forest walk and look at dramatic cliffs dropping into deep valleys. The air shift is part of the appeal, with towering gums and that cooler, shaded feeling that contrasts nicely with vineyard heat.

This stop matters because it breaks the day into two different types of pleasure. First, you are doing taste and town wandering. Then you move into nature mode, where your senses reset and your legs get a short working stretch.

A practical note: wear comfortable shoes. Even if the walk is not described as a major hike, forest paths and viewpoints typically reward sturdy footing. If you tend to get cold in shaded areas, bring a light layer too, since the temperature can drop when you move into the trees.

Bowral in the afternoon: boutique shopping at a slower pace

In Bowral, the day shifts to boutique and antique stores. This is your chance to slow down and shop in a way that feels more like wandering than sprinting.

Bowral is a natural fit after Fitzroy Falls because the vibe changes again, from forest intensity to gentle town rhythm. If you like souvenirs that feel local, the antique and boutique angle is exactly the right kind of contrast to buying a bottle at a cellar door.

If you want to be efficient, give yourself a shopping target: one or two stores or one type of item, like ceramics or small gifts. That keeps the afternoon from eating up the energy you may want for the final farm picnic.

Boscobel Farm: the picnic ending with kangaroos nearby

The day closes at Boscobel Farm, described as a private sanctuary among forest and pasture. A picnic is set under wide country skies, and the highlight detail is that wild kangaroos graze nearby.

This ending is why the whole itinerary feels balanced. After wine tastings and town wandering, you get an unhurried outdoor moment. And because it is a farm setting, it is not just a meal stop. It is the kind of quiet finish where you can look around, talk, and let the day settle.

Bring a sensible mindset here: kangaroos can appear, but the day’s main plan is still the picnic. If you see them, it will be a bonus; if you do not, you still get that peaceful farm atmosphere.

How the tastings and snacks fit together (and how to enjoy them)

The experience includes snacks plus wine tastings. Even without specifics on how many pours you will get at each estate, the structure is clear: tastings are built into vineyard stops, and food helps you keep moving comfortably.

Here’s how to make tastings enjoyable rather than exhausting:

• Take small pours you can compare, then pause and taste again after a few bites.
• Drink water between tastings if you can. It keeps your palate sharper for later stops like Bowral.
• If you plan to buy wine, pick one or two styles you genuinely liked, not what just tastes good in the moment.

This is also a private tour, which typically means fewer hard-and-fast group pressure points. You can ask questions during tastings and get a better feel for the wines being poured.

Private tour perks: why this feels different from a big group day

This is a private tour/activity, meaning only your group participates. That is a meaningful difference when your day includes multiple places, a waterfall walk, and a picnic finale.

With a private format, you are more likely to get attention during the day, especially during tastings where questions and preferences matter. The reviews you provided also underline that the host, Sam, took care of pickup to drop-off and made the day run smoothly, without turning it into an assembly line.

If you value control over pacing, private is the way to go. If you prefer social energy and meeting lots of new people, you might prefer a shared group tour instead. But based on how this day is designed, the calm and countryside feel fits private travel really well.

Who should book this Southern Highlands winery day

This tour is a strong match if you like wine but also want a full day that mixes more than just cellar doors. You will probably enjoy it most if you:

• want a scenic day outside Sydney with village charm
• like cool-climate wine tastings paired with local produce
• enjoy a nature stop like a waterfall walk
• want a relaxed ending with a farm picnic and wildlife nearby

It is also well suited for couples and small groups who want a smoother experience with pickup and a route that covers several standout Southern Highlands stops.

If you hate walking at all, the Fitzroy Falls forest walk might be the part to question. The day is not described as an extreme hike, but it is still a walk on uneven ground.

Should you book it or look elsewhere?

I would book this if you want a well-rounded Southern Highlands day that feels curated toward atmosphere, tastings, and real scenery, not just driving time. The value is strongest for wine lovers who also appreciate Berrima and Bowral, because those town stops help the day feel like more than a set of cellar visits.

I would hesitate if lunch is a big deal for you and you do not want to plan on paying for it. Also, if you only want wineries and no walking, the Fitzroy Falls component may not fit your style.

If you do book, set yourself up for success by wearing comfortable shoes, bringing a light layer for the cooler waterfall air, and deciding ahead of time how you want to handle lunch spending.

FAQ

How long is the Southern Highlands luxury private winery tour?

It runs for about 10 hours.

What does the tour cost?

The price is $411.52 per person.

Is pickup included?

Pickup is offered.

What is included in the price?

The tour includes snacks and wine tastings.

Is lunch included?

No, lunch is not included.

Is the tour private?

Yes. It is private, and only your group will participate.

What time does the tour start?

The start time is 8:00 am.

How much wine tasting should I expect?

Wine tastings are included as part of the experience, with tasting stops at vineyard estates.

Can I cancel for a full refund?

Yes, you can cancel up to 24 hours in advance for a full refund, based on the experience’s local time.