Kangaroos and cool-climate wine in one day. This private Southern Highlands tour strings together Berrima’s sandstone village, multiple estate stops, and a farm picnic that ends with wildlife sightings.

I really like how the day mixes wine tastings and food-style stops with real scenery breaks, so it never feels like you’re just hopping from one cellar door to the next. I also like the level of care in the flow of the day, with pickup and drop-off handled by the host (Sam is mentioned in customer feedback) and a calm, unhurried rhythm.

One thing to keep in mind: lunch isn’t included, even though you’ll have a dedicated lunch stop on the route. Plan for extra food spending, and expect a full 10-hour day with a couple of walking moments.

Key highlights you can plan around

• Private group setup: only your group participates, so you’re not sharing the van with random strangers.
• Cool-climate tasting focus: snacks plus wine tastings build the day around regional flavors.
• Berrima + Bowral pacing: small-town lanes for atmosphere and boutique shopping, not rush-you-through stops.
• Fitzroy Falls scenery break: forested cliff views and a short nature reset between tasting moments.
• Boscobel Farm picnic finale: picnic-style ending with wild kangaroos grazing nearby.
• Pickup and drop-off included: helps you avoid parking, timelines, and transit stress.

Southern Highlands at a relaxed pace: from Berrima to Boscobel Farm

This is the kind of day trip that works because it has structure. You start in Berrima, then the route builds from village charm into vineyard country, with a waterfall stop and a nature finale at Boscobel Farm. Even with all the stops, the tone stays low-key.

The private format matters more than you might think. Instead of waiting around, you keep a smoother timeline as the host drives you between places you’d have trouble stitching together on your own without a lot of planning. It’s also a nice fit if you want conversation and recommendations without the chaos of a big shared group.

Your day is scheduled for about 10 hours, starting at 8:00am, so it’s a “use the whole day” kind of outing. If you like slow travel, this still scratches that itch, because Bowral and Berrima are built for wandering.

Price and value: what $411.52 buys for a 10-hour private wine day

At $411.52 per person, this isn’t a budget day trip. You’re paying for private transport from Sydney, a guided itinerary with multiple set stops, and tasting time rather than just driving past vineyards.

Here’s what you actually get inside the experience: snacks and wine tastings are included. You’ll also have pickup offered and a mobile ticket, and the tour is designed so only your group participates. “Admission ticket free” is listed for the experience, which is a helpful cost saver if you’re used to paying for small attraction entries on top of transport.

The one clear gap is lunch. Lunch is not included, even though you’ll have a lunch point on the day. So if you book this, I’d treat the listed price as your core spend for tastings and transport, then budget separately for lunch at the stop where it’s offered.

In plain terms: it’s best value if you’d otherwise spend real money on wine tasting bookings plus a private car/driver, and you want someone to manage the day. If you’re the type who likes to “just figure it out” and you’re comfortable driving rural routes, a DIY itinerary could be cheaper. But it would be more work.

Berrima’s sandstone lanes and colonial-era atmosphere

Your day begins in Berrima, a village known for sandstone cottages and a colonial-era feel. This is a good first stop because it slows your brain down right away. Instead of being thrown straight into wineries, you get to ease into the Southern Highlands look and feel.

In practical terms, Berrima is also a great place to reset before wine tastings. You can do a bit of casual wandering, take in the architecture, and get your bearings for the rest of the route. If you’re the kind of person who likes photos but hates the “stand here for 20 seconds” feeling, this village part helps.

The host also covers stories while you travel between points. That kind of context matters in wine country because it turns a tasting visit into something you can actually remember beyond the flavor notes.

Mount Ashby Estate: French-style cuisine stop and homestead charm

Next up is Mount Ashby Estate, which is described as a boutique vineyard with French-style cuisine, local wines, and a homestead framed by art and stables. That combination is a big part of the appeal: it feels like you’re stepping into a composed country setting, not just a tasting room.

Even though lunch is not included in the package price, the stop itself is part of the experience. The itinerary notes French-inspired charm, antiques, and sweeping paddocks, which gives you time to enjoy the estate atmosphere rather than rushing straight through a tasting.

One practical tip: if you’re sensitive to long days, this is where you’ll likely want to take advantage of the slower pacing. You can treat Mount Ashby as your “fuel stop” even if the food costs extra. And since you’ll have already had snacks on the way, you won’t feel totally empty going into lunch.

Fitzroy Falls: waterfall air, cliff viewpoints, and a nature break

After the estates, the itinerary shifts toward Fitzroy Falls. This is the scenery reset: forested cliffs and deep valleys, with a walk to a striking waterfall area surrounded by tall gums and cool air.

I like this stop because it keeps the day balanced. A wine day can start to blur if every stop is sensory-similar. The falls segment gives you something different to look at and photograph, plus a physical stretch that feels like you earned it.

One consideration: it’s still part of a 10-hour day, so your comfort level for walking matters. The information provided mentions a forest walk, so wear shoes you’d be happy to step around in. If you’re prone to sore feet, bring some extra water and keep your pace steady.

Bendooley Estate: cheese and wine tasting around lakeside vines

Bendooley Estate is the other key tasting anchor, with a cheese-and-wine setup. The tasting is described alongside a charcuterie board featuring regional produce, and the grounds are noted as lakeside vines with manicured character.

This is where the “cool-climate” focus makes sense. The Southern Highlands is known for a distinct style, and spending time here (instead of doing one quick pour-and-go tasting) gives you the chance to actually compare impressions across the day.

I’d treat this stop like a guided learning moment. You’ll have snacks included, plus tasting time, so you can slow down and listen to what the host explains. If you’re buying wine later, this is also where you’ll be able to connect a bottle you like with a place you remember.

Bowral boutique wandering and antique-store browsing

In the afternoon, the day moves to Bowral, and the tone shifts again. Bowral is where you get boutique stores and antique browsing, which is a different kind of value than a winery tasting.

This shopping time is important because it gives you control. You can spend 20 minutes in a shop that catches your eye, or linger longer if you spot something special. It also helps the day feel less like a schedule and more like a country afternoon.

If you want a practical approach, set a simple goal for Bowral: one small souvenir, one snack, and then stop. Otherwise it’s easy for shopping to eat the last energy of the day—especially when you still have a farm picnic waiting.

Boscobel Farm picnic finale with kangaroos nearby

The day ends at Boscobel Farm, described as a private sanctuary among forest and pasture. Your picnic is set under wide country skies, with the bonus of wild kangaroos grazing nearby.

This kind of ending is what makes the whole day feel memorable. It’s not just another tasting room; it’s a countryside moment. Even if you’re not a wildlife person, it’s a visual payoff that feels genuinely Southern Highlands.

A small practical note: picnics are nice, but you’ll want to be ready to sit outside for a while. The climate can shift in cooler regions, so bring a layer you’d be comfortable wearing even if the sun drops.

And if you’re the type who loves that “one last look before leaving” feeling, this is your moment. After a full day of tastings and scenic stops, kangaroos grazing at the edge of your picnic area turns the trip into a story you’ll tell later.

Who this private tour suits best (and who might prefer DIY)

This tour is a strong match for you if you want a guided Southern Highlands day without planning the logistics yourself. It’s also a good fit if you like tasting with structure—snacks included, tastings planned, and time built in for both villages and scenery.

It’s especially ideal for couples or small groups who want private pacing and fewer interruptions. Private doesn’t just mean comfort; it can mean you get better attention and a more relaxed experience when asking questions about wine and the region.

You might prefer a DIY approach if you’re cost-first, you already know you only want one tasting stop, or you’re happy to drive between vineyards, parks, and village streets on your own. Still, this itinerary is built from a series of distinct place-types—village, estates, waterfall country, shopping, and farm picnic—and that blend is hard to replicate without a plan.

Should you book this Sydney-to-Southern-Highlands luxury winery tour?

If you want an organized, private day that mixes wine tastings, estate atmosphere, Fitzroy Falls nature, and a picnic ending near kangaroos, I’d say it’s worth considering. The included snacks and wine tastings, plus pickup and drop-off, do real work to reduce decision fatigue.

Just go in with two expectations set: it’s a full 10-hour day, and lunch isn’t covered in the package. If that fits your style and budget, you’ll get a well-paced Southern Highlands day that feels more like a carefully planned escape than a hurried checklist.

FAQ

What’s the duration of the tour?

The tour runs for about 10 hours.

What time does the tour start?

It starts at 8:00am.

How much does the tour cost?

It’s priced at $411.52 per person.

Is pickup included?

Pickup is offered.

Is this a private tour?

Yes. It’s private, and only your group participates.

What’s included in the price?

Snacks and wine tastings are included.

Is lunch included?

No. Lunch is not included.

Where does the tour focus during the day?

You visit Berrima, Mount Ashby Estate, Fitzroy Falls, Bendooley Estate, Bowral, and end at Boscobel Farm.

Is a mobile ticket provided?

Yes, the tour includes a mobile ticket.

Can I cancel for a full refund?

Yes. Free cancellation is available up to 24 hours in advance for a full refund.

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