A cool-climate wine day beats guesswork. This private luxury tour runs about 10 hours and strings together Berrima village, wine tastings, Fitzroy Falls, Bowral shopping, and a final farm picnic, all with pickup so you can relax. I like that it feels paced and easy, not rushed, while still giving you real stops to taste and look around.

The one thing to watch is food planning: lunch isn’t included, so you’ll want to budget for meals on the day (even though snacks are provided).

Key highlights at a glance

• Berrima first: sandstone cottages and a calm, colonial-style start
• Bendooley Estate tasting: cheese and cool-climate wines in a scenic setting
• Mount Ashby Estate lunch time: French-inspired vibe, wines, and an art-and-stables homestead feel
• Fitzroy Falls forest walk: cool air and big waterfall views between tastings
• Boscobel Farm finale: picnic among forest and pasture, plus kangaroos when they’re out
• Sam J care: praised for looking after the group from pickup to drop-off

A luxury Southern Highlands day from Sydney, without the driving headache

The Southern Highlands is built for an easy wining-and-wandering day. You get cool-climate vineyards, old-style village streets, and nature that actually interrupts the tasting rhythm (in a good way). And because this is a private tour for only your group, you’re not competing for space or listening to someone else’s idea of fun.

Your day starts at 8:00 am and runs about 10 hours. That’s long enough to feel like a proper outing, but it’s still a single-day plan from Sydney. The payoff is you can leave the navigation, parking, and timing to the people running the trip.

If you like the idea of tasting wine in a small, controlled schedule—rather than doing a freestyle drive where half your day disappears—you’ll appreciate how this one is structured. You’ll also get snacks along the way, which helps when you’re between tasting pours and meal time.

Berrima village: sandstone charm and a calm start

The first stop sets the tone: Berrima, known for sandstone cottages and early colonial character. Think slower streets, classic building shapes, and that feeling of you being somewhere that has hosted travelers for a long time—without needing to hustle for it.

This is a good first move because it works like a reset button. Before you hit the vineyards and waterfalls, you get a gentle entry into the region. And since your day is private and paced, you don’t have to do the usual tourist-speed checklist.

Practical tip: wear comfortable shoes. Even if you’re not doing a long walk, village time adds up, and you’ll want to be able to wander without feeling grumpy halfway through.

Bendooley Estate: cheese and cool-climate wine tastings with lakeside vibes

Next comes Bendooley Estate, where the main event is a tasting with cheese and cool-climate wines. The setting matters here. You’re tasting among lakeside vines and manicured grounds, so it feels like more than just a sip-and-run stop.

I like that the tasting is paired thoughtfully. Wine tastes better when you’re also eating something that matches it, and the tour builds that rhythm in. It also keeps the day balanced—this isn’t only wine and nothing else.

What to expect: you’ll be sitting down for the tasting experience, not just standing around. You’ll also likely see how the estate frames its vineyard views, which makes the whole thing feel less generic. If you enjoy learning what you’re drinking, this stop is a natural place to pay attention.

One consideration: tastings can make you a little too relaxed. The next part of the day includes more moving around, so pace yourself with your pours.

Mount Ashby Estate: French-style charm, local wines, and a homestead feel

After Bendooley, the tour heads to Mount Ashby Estate, a boutique vineyard known for French-style cuisine and local wines. You’re not just tasting here—you’re stepping into a specific atmosphere: an estate homestead framed by art and stables, plus sweeping paddocks.

This stop is a highlight if you like estates that feel designed for lingering. There’s time to slow down, enjoy the setting, and focus on wine rather than logistics. And yes, there’s a lunch element mentioned as part of the day, but the ticket does not include lunch. That means you should plan on paying for your meal during the stop.

My advice: treat this as your “proper meal moment” and go in with an appetite. Snacks help, but lunch is what turns a tour day into a full experience.

If you’re the type who hates making food decisions under time pressure, consider looking over your options quickly and choosing something that won’t be a struggle if you end up buying a second tasting after. It’s a long day, and energy management is real.

Fitzroy Falls: a forest walk that breaks up the tasting day

Then comes the nature chapter: Fitzroy Falls. The tour moves from vineyards to cliffs and deep valleys, and the centerpiece is a forest walk toward a striking waterfall view.

This stop is valuable because it gives you contrast. After wine, cheese, and estate scenery, the cool air and towering gums reset your senses. It’s also a reminder that the Southern Highlands isn’t just about cellars—it has dramatic terrain that you feel with your body when you’re walking.

What to expect: a walk in a forest setting, followed by time to take in the waterfall and surrounding views. The route is described as cool air with towering gums, so even if the day is warm, you might feel temperature changes under the trees.

Practical tip: bring grippy shoes. You might not be doing a hardcore hike, but you will be walking on paths that can be uneven.

Bowral: boutique stores and antiques at a slower rhythm

Once you’ve got your waterfall fix, the day softens again in Bowral. This is where the pace becomes more leisurely and the region’s craftsmanship shows up in shops—especially boutique stores and antiques.

I like stops like this because they help you take home something beyond a souvenir bottle. You get a feel for the local design and browsing culture, without needing a reservation or a ticket.

What to do here: browse and walk your own path. This part works best if you’re not trying to rush. The tour time gives you enough room to look around, but you still benefit from having a guide coordinating the schedule so you don’t end up late for the next leg.

If shopping isn’t your thing, you can still use Bowral time for a reset—coffee, a short stroll, and regrouping before the farm finale.

Boscobel Farm: the picnic finale with wild kangaroos nearby

The day ends at Boscobel Farm, described as a private sanctuary among forest and pasture. The key vibe is wide country skies and a picnic set out to enjoy while kangaroos graze nearby—when they’re out.

This is the kind of ending that makes the whole tour feel complete. You’ve had tastings, walking, and village time. Then you close with open space and a relaxed meal moment. It’s a nice contrast to the structured tasting format earlier in the day.

What makes this stop special for your day: it slows everything down right at the end. You’re not rushing to fit one more winery or trying to find food before closing time. You’re given a comfortable finish.

A small consideration: wildlife sightings are never guaranteed on a schedule. The tour information notes that kangaroos graze nearby, and the overall impression from the trip experience has included kangaroos showing up. Just know you’re going to be looking more than hunting for them.

Price and logistics: is $411.52 per person good value?

At $411.52 per person for about 10 hours, this isn’t a budget tour. It’s in the “pay for convenience and a curated day” category. So the real question is what you’re getting for that spend, and for your particular travel style.

Here’s the value picture:

• You get pickup offered, which removes the hardest part of a countryside day: the driving and timing stress.
• Wine tastings are included, which would cost you time and money if you tried to stitch together the same stops on your own.
• Snacks are included, so you’re not running on empty between winery moments.
• It’s private, meaning only your group participates. That matters if you want a more personal pace and fewer interruptions.

The main trade-off is food. The tour states that lunch isn’t included, even though lunch time is part of the day flow at Mount Ashby Estate. You can treat that as your budgeting moment: decide what you want to spend and keep the rest of the day easy.

Who should book this:

• Couples and small groups who want a relaxed, high-effort itinerary without planning every stop
• Wine lovers who like guided tastings more than self-driving trial and error
• People who enjoy a mix of food, nature, and shopping in one day

Who might want to think twice:

• Anyone who hates long days. Starting at 8:00 am and finishing around 10 hours later is real time on the road.
• Anyone who wants all meals included. If you prefer a fully ticketed food plan, this one may feel a bit incomplete at lunchtime.

Should you book A Day In The Vineyards from Sydney?

I’d book it if you want a polished Southern Highlands day where the hard parts are handled: transport, the pacing between stops, and guided wine tastings. The mix of Berrima, Bendooley’s cheese-and-wine format, Fitzroy Falls walking, Bowral shopping, and the Boscobel Farm picnic ending is exactly the kind of itinerary that usually takes way longer to build on your own.

I’d hesitate if lunch inclusion is a dealbreaker for you, or if you’re not comfortable with a full schedule that starts early. But if you’re okay budgeting for your meal and you like the idea of a guide coordinating the day, this tour is a strong match for a memorable countryside outing without the stress.

FAQ

What time does the tour start?

The tour start time is 8:00 am.

How long is the experience?

It runs for approximately 10 hours.

Is this tour private?

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

Is pickup included?

Pickup is offered as part of the tour.

What is included in the ticket price?

Snacks and wine tastings are included.

Is lunch included?

No, lunch is listed as not included.

What ticket format do I use?

You’ll receive a mobile ticket.

Are group discounts available?

Yes, group discounts are mentioned.

Can I cancel for a full refund?

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

Are service animals allowed?

Yes, service animals are allowed.