A day of green hills and waterfalls beats the city pace. This private Southern Highlands outing from Sydney mixes Fitzroy Falls, heritage towns, and wine tasting, so you get variety without the hassle of planning. It also runs on a true pickup-and-dropoff day, which matters when you’re trying to make the most of limited time.

What I like most is the private, only-your-group setup—your guide can shift the pace to fit your mood. I also like that paid experiences are rolled in, including wine tasting fees and garden entry, so you’re not constantly checking what costs extra.

One thing to consider: it’s a packed 10-hour route with short stops, so if you want slow wandering all day, you may feel a bit time-pressed during transitions and photo breaks.

Key reasons this Southern Highlands tour works

• Private guide attention for a smoother, more flexible day than DIY
• Fitzroy Falls with an easy shot to see the falls from the top track
• Red Cow Farm Garden that’s calm, walled, and designed for slow looking
• Heritage time in Berrima on its restored sandstone main street
• Wine tasting at Bendooley Estate with cool-climate wines as the focus
• Hotel pickup and drop-off that saves time in Sydney traffic

Getting out of Sydney: why this route feels like a real reset

Leaving Sydney for the Southern Highlands is the point, and this tour does it in a clean, no-stress way. You start at 8:00 am with pickup from central-Sydney hotels, and you’re back the same day. That means you avoid the usual day-trip problem: too much time spent commuting and not enough time actually seeing the countryside.

The itinerary also mixes “wow” with “wander.” You get natural scenery at Fitzroy Falls, then you pivot to gardens and village streets. That’s a smart rhythm for a private day trip, because it keeps the day from turning into only photos or only shopping.

And if you care about comfort and flow, the guide experience seems to be a big part of the value. People mention guides like Glenn (and the day staying fun and entertaining), plus a nice ride—exactly what you want when you’re spending most of your day on the road.

The day plan in plain English: Bowral, Fitzroy Falls, Red Cow Farm, Berrima, wine

This is built as a classic Southern Highlands “best-of” route, but with enough time at each stop to actually enjoy it. Expect about 10 hours total, with a mix of free time and included activities.

Here’s how the pacing usually lands:

• Bowral (about 1 hour): an easy start in rolling green hills, with time to breathe and get your bearings.
• Fitzroy Falls (about 20 minutes): quick but satisfying nature time, with the included track to the top viewpoint.
• Red Cow Farm Garden (about 1 hour): a focused garden stop with paid entry included.
• Berrima (about 1 hour): heritage village time on the single main street and shops.
• Wine tasting at Bendooley Estate (about 1 hour): a structured tasting visit with fees included.

You’ll also have bottled water, which sounds small until you’re halfway through the day and grateful you don’t have to search for it.

Bowral first: where to land before the falls and gardens

Bowral is the gentle on-ramp to the Southern Highlands. You’ll spend about an hour here, and it’s the kind of stop that helps the rest of the day make sense. Instead of jumping straight from Sydney into a big attraction, Bowral lets you shift gears—more fresh air, more open space, and a calmer start.

You’ll also get a taste of the region’s old-village atmosphere. The Southern Highlands are known for that heritage-village feel, and Bowral is a logical first step before you head into Berrima, which is where the Georgian streets really come to the front.

Practical tip: treat Bowral like your “reset hour.” Walk a bit, take a few photos, then use the rest of your energy for the garden and falls.

Fitzroy Falls: that short top-track photo stop

At Fitzroy Falls National Park, you’ll get around 20 minutes—not long, but intentionally timed. The tour includes admission and focuses on the short walk that gets you to the falls from the top.

For most people, this is the sweet spot: enough time to see the falls properly and take your photos, but not enough time to drag the whole day down with a long hike. If you want nature without turning the day into a fitness project, this stop fits.

Two quick expectations to set right:

• This is mainly a viewpoint experience, not an all-day trail system.
• Your best photos depend on the day’s light, so if it’s pouring or gloomy, you may want to adjust your expectations for contrast and visibility.

Red Cow Farm Garden: a walled sanctuary kind of pause

Then comes a quieter change of pace: Red Cow Farm Garden, a privately owned property on about 2.5 hectares. You’ll have about an hour, and garden entry is included.

This is the sort of place where the design does half the work for you. The garden includes features like a walled sanctuary, plus different sections such as a monastery garden and abbess’s garden. That gives you a structured way to look—like you’re moving through separate “rooms” of greenery rather than wandering randomly.

If you’re the type who likes details, this is also where a guide can help. A good private guide can point out what to focus on during your hour so you leave feeling like you actually saw the place, not just walked through it.

Practical tip: wear comfortable shoes. Even though it’s not described as a hike, gardens can add up to lots of walking on uneven paths.

Berrima’s Georgian street: heritage shopping time that doesn’t overstay

After the garden calm, you’ll jump into village life in Berrima. You get about an hour, and this is a free-time style stop. Berrima is described as a 1830s Georgian village, and the main attraction is its restored sandstone architecture along the village’s only street.

This is a fun stop if you want:

• photos of historic buildings that look like they belong in a storybook,
• a slow wander where you can choose how active you want to be,
• and specialty shops for local arts and crafts.

A key drawback to keep in mind: one street means your best use of time is doing a round-trip walk, then choosing a couple shops (instead of trying to do everything). With only about an hour, you’ll enjoy it more if you go in with a plan: browse first, then linger where something actually catches your eye.

Bendooley Estate wine tasting: what’s included and how to make it count

The wine portion happens at Bendooley Estate, and it’s included for about an hour. The tasting is focused on boutique cool-climate wines, grown under the region’s conditions of cool nights and mild days with dry ripening.

Even if you don’t consider yourself a “wine person,” this stop tends to work for two reasons:

1. it’s scheduled like a real visit, not a random roadside pour, and
2. it’s paired with the scenic Southern Highlands theme of the whole day.

Important rule: the minimum drinking age is 18 years.

Practical tip for making the tasting experience feel worth it: pace your sipping. You’re doing multiple stops in one day, and wine makes the day more enjoyable when you don’t rush or overdo it.

Also note what’s not included: food and drinks aren’t included unless specified. So plan to handle lunch on your own.

How the private guide (like Glenn) changes the whole day

The reviews strongly point to one thing: the guide can make a big difference. People call out Glenn for being knowledgable and enthusiastic, plus making the day feel fun and entertaining. That kind of guide energy matters when you have a fixed route and you’re in and out of stops quickly.

A skilled guide can also make your downtime smarter. For example, someone mentioned Glenn taking them to a great little pub for lunch. Even if lunch isn’t included, a private guide can help you find something that fits your taste and timing, instead of you guessing while hungry in a town you don’t know.

Private also means your group can ask questions in the moment. If you’re curious about what you’re seeing at Fitzroy Falls or what to look for in the gardens, the answers don’t feel like a scripted lecture. It’s more like having a local explain why this area looks the way it does.

Price and value: does $523.59 per person add up?

At $523.59 per person, this isn’t a cheap day trip. But it includes several value pieces that many cheaper tours leave for you to pay separately.

From what’s included, you’re getting:

• private tour time (not shared with random strangers),
• hotel pickup and drop-off from central Sydney,
• wine tasting (including wine tasting fees),
• Red Cow Farm Garden entry,
• Fitzroy Falls admission,
• and bottled water.

That combination changes the math. If you were to DIY the route, the driving time from Sydney alone can eat up most of your day, and you’d still need to buy tickets and manage where to stop and when.

The tour also mentions group discounts, which can matter if you’re splitting the cost with people you travel with. Since it’s a private setup, the best value tends to show up when you can spread the price across your group rather than going solo.

My take: it’s a strong choice if you want a guided day with paid stops handled and you’d rather pay for convenience than negotiate logistics.

Who should book this Southern Highlands private tour?

This is a good match if you want:

• a 10-hour escape from Sydney that still feels structured,
• a route that mixes nature, gardens, and heritage towns,
• wine tasting included, with the tasting time built into the schedule,
• and the comfort of pickup/drop-off.

It’s also a great option for couples, small friend groups, and anyone who has limited time in Sydney but still wants to see beyond the city.

Where it may not fit: if you love long hikes, this day is more short-walk and viewpoint focused. If you want hours of unstructured wandering, the stops are deliberately timed, so you’ll need to treat each one as a “good look” moment rather than a long stay.

Should you book this Southern Highlands private tour?

If you’re trying to choose between DIY and guided, I’d lean toward booking if your priority is less driving stress and more planned experiences. The biggest reasons are the included paid elements—wine tasting, garden entry, and Fitzroy Falls admission—plus the hotel pickup that keeps your day-trip window from shrinking.

I’d skip it only if you know you’ll resent a tight schedule, or you don’t care about wineries, gardens, or heritage towns and want a different kind of day (more beach, more hiking, or more time in one place).

If you land in that middle sweet spot, this route is an efficient, enjoyable way to experience the Southern Highlands without turning your day into a checklist.

FAQ

How long is the Southern Highlands private tour?

It runs for about 10 hours (approx.).

What time does the tour start?

The start time is 8:00 am.

Is hotel pickup and drop-off included?

Yes. Return transfers from central-Sydney hotels are provided, and hotel pickup and drop-off are included.

Is this tour really private?

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

What are the main stops during the day?

You’ll visit Bowral, Fitzroy Falls, Red Cow Farm Garden, Berrima, and go to Bendooley Estate for wine tasting.

Is wine tasting included, and what’s the age limit?

Wine tasting is included, and the minimum drinking age is 18 years.

What admissions or entry fees are included?

Wine tasting, Fitzroy Falls admission, and Red Cow Farm Garden entry are included (and you’ll also have bottled water).

Are meals included?

Food and drinks are not included unless specified.

What if I need to cancel?

You can cancel for a full refund up to 24 hours in advance of the experience’s start time.

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