Ten hours can feel short when the scenery keeps changing. This luxury private winery tour takes you from sandstone-streets calm in Berrima to cool-climate tastings and a country-farm picnic. I like that it’s built around food and small discoveries, not just check-the-box wineries.

I also like the guide-led flow, especially with Sam. He looked after the group start to finish and helped turn the drive into more than just road time. Wine tastings and tasting-paired bites are a big part of the value, so you’re not left wondering what to do after you arrive.

One thing to consider: lunch isn’t included. You’ll have snacks, tastings, and a picnic setup at the end, but you’ll want to plan around the fact that a full included lunch isn’t part of the package.

Key Points That Make This Tour Work

• Berrima’s colonial charm sets a relaxed pace before the vineyard stops begin
• Mount Ashby Estate brings French-inspired cuisine vibes alongside local wines
• Fitzroy Falls adds a cool-air forest walk between tastings
• Bendooley Estate pairs wine with cheese tasting in a scenic garden setting
• Bowral and its antiques give you a slower shopping window after the countryside
• Boscobel Farm picnic with kangaroos finishes the day on a distinctly Aussie note

Southern Highlands Morning: Berrima’s Sandstone Starts the Day Right

You start early (8:00 am) and move straight into the Southern Highlands mood. Berrima is the kind of place where the details matter: sandstone buildings, a colonial-era feel, and streets that encourage you to slow down instead of rush. It’s a smart opener, because it helps you reset before the tasting part gets serious.

What you’ll like here is the contrast. This isn’t an all-drive, all-hurry day. You get real village time early on, which makes the rest of the itinerary feel intentional instead of jammed into a long vehicle ride.

Practical tip: wear comfortable walking shoes. Even if your “exploring” is just a gentle stroll, sandstone sidewalks and village lanes add up over a morning.

Mount Ashby Estate: French-Inspired Bites, Local Wines, and a Homestead Feel

After Berrima, you roll through farmland toward Mount Ashby Estate. This is where the tour turns into a food-and-wine day in earnest. Expect French-style cuisine influences, local wines, and a homestead setting framed by art and stables. The point isn’t fancy performance—it’s that lived-in country vibe where wine feels like part of the landscape (literally) rather than a separate event.

The tasting format helps too. You’re not just tasting random pours. You’re moving from Berrima’s village calm into a place that clearly values hospitality, so the wines come with context—how they fit the region’s cool-climate character and the day’s menu-like pacing.

A small drawback for some people: this stop can feel like it’s leaning more toward tasting and atmosphere than a long winery history lecture. If you’re the type who wants deep technical winemaking info, you might still get plenty of discussion, but the experience is clearly designed around enjoyment and pairings.

Fitzroy Falls: A Forest Walk That Breaks Up the Wine Time

Then you switch gears at Fitzroy Falls. Instead of more cellars and tasting rooms, you’re looking at forested cliffs dropping into deep valleys, with a standout waterfall experience. The air is cooler here, and the walk through towering gums gives your body a reset after hours of sitting and tasting.

I love this part because it changes the pace in a good way. If all day you’re tasting and shopping, your palate and attention can get tired. A proper outdoor stop keeps the day from turning into a blur of sips.

What to do: take a moment to step away from your photos and actually listen to the place. It’s the kind of natural pause that makes the last two stops feel special instead of routine.

Bendooley Estate: Cheese and Wine Tasting by Lakeside Vines

Bendooley Estate is where the day becomes more picnic-level enjoyable, even before the final farm stop. You’ll do a cheese and wine tasting in a setting with lakeside vines and manicured grounds. This is one of those pairings that’s easy to enjoy because it’s not complicated. You taste, you compare, you snack, and you keep moving at a comfortable rhythm.

For cool-climate wine country, this kind of pairing matters. Cheese and wine isn’t just food—it’s a practical way to taste across styles and get your palate synced up to the region. You’ll walk away with a few favorites you can actually remember, not just a list of things you sampled.

A consideration: if you’re very sensitive to strong cheese aromas, you’ll still likely be fine, but this is a tasting stop built around food. Go in hungry enough to enjoy it, but not so stuffed that you miss the wine notes.

Bowral Break: Antiques, Boutiques, and a Slower Rhythm

By the time you reach Bowral, the tour gives you breathing space. Bowral is known for slower shopping—boutique shops and antique stores—so this is your chance to wander without feeling like you’re racing to the next appointment.

I think this stop is smart because it gives your day balance. You’ve had food, nature, and vineyards; then you get to do something local and unhurried. If you’re the type who collects small souvenirs, this is a good window. If you’d rather just browse, you can keep it casual.

Tip: don’t overpack on your first stops. Bowral shopping can tempt you, and you don’t want to be carrying extra bags for the last leg of the tour.

Boscobel Farm Finale: Picnic Under Country Skies and Kangaroos Nearby

The day ends at Boscobel Farm, which has the feel of a private sanctuary tucked between forest and pasture. This is where you finish with a picnic-style setup under wide country skies. And yes, kangaroos can be grazing nearby, which is exactly the kind of Australia moment that doesn’t feel staged.

This ending works because it’s a “hold onto it” moment. After tastings and stops, you get to sit, snack, and take in the open space. It also makes the day memorable in a way wine tours sometimes miss: you’re not only tasting products; you’re experiencing the place.

One more practical note: keep your camera handy, but also keep a few minutes to just watch. The kangaroos (when they’re out) aren’t there for a photo—so let them do their thing.

Price and Value: What You’re Paying For at $411.52

At $411.52 per person for about 10 hours, this tour isn’t a budget afternoon. It’s a premium day built around logistics and guided tasting time. The value comes from three things you don’t have to manage yourself:

First, pickup is offered, which matters because winery days are harder when you’re planning transport. Second, wine tastings and snacks are included, so you’re not constantly paying extra just to keep the day moving. Third, you’re getting multiple distinct stops—village, estate dining atmosphere, waterfall walk, cheese-and-wine pairing, boutique wandering, and a farm picnic—so the day feels like an actual itinerary, not random hopping.

One important reality check: lunch isn’t included as a named item. If you expect a full sit-down lunch included in the price, plan differently. In practice, the snacks and end-of-day picnic setup soften that gap, but you should still be ready to spend a bit if your appetite runs strong.

If you want a day that feels organized, hosted, and easy—this price makes sense.

What It Feels Like: A Private Day With a Real Host

This is a private tour, meaning it’s just your group. That changes everything about the pace. You can move through tastings without the constant churn of strangers, and your guide can adjust the rhythm more naturally to your group’s comfort level.

Sam is a big reason people rave about this experience. The feedback points to smooth care from pickup to drop-off, plus the way he ties the places together. That’s not just pleasant guiding; it makes the whole day feel like one coherent story rather than a series of stops.

If you like thoughtful context—like learning about what you’re seeing while the car rolls along—you’ll appreciate this style.

Who Should Book This Southern Highlands Winery Tour

This tour fits best if you want a luxury-feeling day without having to plan every detail yourself. I’d especially recommend it if you:

• enjoy wine tastings but want the day to include more than just wineries
• like nature breaks between tastings (Fitzroy Falls is a key reason)
• prefer a private format over crowded group tours
• want a classic Southern Highlands mix: village charm, estate dining vibe, boutique time, and a country-farm finale

It may not be perfect if you’re looking for a long, deep technical wine class, or if you strongly dislike long road time. The day runs around 10 hours, and that’s a factor.

Should You Book This One?

I’d book it if you want a hosted day where tasting is only one piece of the experience. The combination of Berrima’s sandstone atmosphere, Mount Ashby’s French-inspired estate feel, a cool-air Fitzroy Falls walk, Bendooley’s cheese-and-wine pairing, and the Boscobel Farm picnic ending with kangaroos nearby is a rare mix.

I’d think twice if you’re counting on a fully included lunch or you need a very light schedule. Also, because this is a private tour and runs as a full day, you’ll get the best value when your group actually wants to experience everything, not just sample one or two highlights.

If that sounds like your kind of day, this is a strong choice.

FAQ

How long is the tour?

The experience runs for about 10 hours.

What time does the tour start?

It starts at 8:00 am.

How much does the tour cost?

The price is $411.52 per person.

Is pickup included?

Pickup is offered.

What’s included in the price?

Snacks and wine tastings are included.

Is lunch included?

Lunch is not included.

Where does the tour take place?

It runs through the Southern Highlands area around places like Berrima, Mount Ashby Estate, Fitzroy Falls, Bendooley Estate, Bowral, and ends at Boscobel Farm.

Is this tour private?

Yes. It’s a private tour/activity, and only your group will participate.

Are mobile tickets used?

Yes, a mobile ticket is used.

Can I cancel for free?

Free cancellation is available. You can cancel up to 24 hours in advance for a full refund.