Private Southern Highlands Luxury Wine Indulgence Tour

A private wine day 90 minutes from Sydney. This Southern Highlands tour is built for people who want a Mercedes V-Class ride and real breathing room, then to slow down for two cold-climate wine tastings at boutique wineries around 600 meters above sea level. The one thing to think about is timing: it’s about a 10-hour day starting at 8:00 am, so you’ll want an early breakfast and a clear head for the long drive.

I like how the day stays low-key. You travel with only your group, up to 7 guests, and you’re not stuck in a cattle-car schedule. David, the driver called out for knowing the right spots and staying flexible, is a big reason this feels more like a custom day than a checklist.

There are also optional add-ons that let you steer your own pace, like lunch at a historic pub and a brewery stop later on (time permitting, and it runs Wed to Sun for the beer tasting). If you prefer everything fixed and timed with zero choices, the optional parts may feel like a bit of extra decision-making.

Key highlights to know before you go

• Private Mercedes V-Class for up to 7 guests, so the pace feels calm
• Two included wine tastings at cold-climate boutique wineries
• Berrima village time with another included tasting and optional beer at the local pub
• Bowral browsing hour, with time for shops, antiques, or a relaxed break
• Bendooley Estate Book Barn stop, pairing books, a cafe, and an optional tasting
• Mittagong brewery cap-off (Wed to Sun) when timing allows

Why the Southern Highlands are perfect for a cold-climate wine outing

The Southern Highlands sit close enough to Sydney that it works as a true day trip, but they still feel like a world away once you leave the city rhythm behind. The tour route is built around the idea of cooler weather and boutique wineries, not big production lines. That colder elevation detail matters for the vibe, even before you get to a single glass.

You’ll be in the countryside for most of the day. That usually means views you can actually enjoy, plus the kind of driving that feels smooth rather than stressful. And because this is a private setup, you’re not waiting on other groups at every turn. If one winery runs a touch long, or you want a few extra minutes to look around a town, the schedule is designed to flex.

This is also a good region for mixing wine with small-town life. You do more than sip and dash. You get time in places like Berrima and Bowral, where you can reset your senses between tastings and shop at a slower tempo.

Price and value: what $491.31 really buys you

At $491.31 per person, this is not a budget wine day. It’s priced like what it is: a private luxury vehicle with a personal driver, plus two wine tastings included for adults over 18.

Here’s the value math that usually helps most people decide. If you’re splitting the cost across a larger group (up to 7), the private transportation piece becomes much easier to justify. If it’s just two of you, it feels pricier, but you’re still getting:

• Mercedes V-Class transport with bottled water provided
• A full day planned around winery time plus historic town stops
• Two included tastings, which reduces the number of separate purchases you have to make during the day

What’s not included is also important. Lunch and beer tasting are optional, not part of the included package. So if you love food pairings and you also want beer, you should budget extra. But if your priorities are wine tastings plus a relaxed towns-and-shops day, the base price lines up well with those goals.

Mercedes V-Class, private group size, and a day that stays flexible

You start early at 8:00 am, and you’ll spend roughly 10 hours total. The trade-off for that long day is that you get a complete slice of the Southern Highlands, not a short “one winery only” stop.

The group size is a big deal. With only your group in the vehicle (up to 7 guests), you avoid the awkward logistics of a large tour bus. You also get more control over your own rhythm. If your group wants to browse a little longer in Bowral, you’re not stuck because someone else’s timing demands a hard stop.

The tour also includes pickup offered, which matters for lowering friction. You do not need to plan a separate way to reach wineries scattered across the region. Add in bottled water, and it’s one less thing you’ll think about during a full day out.

One more practical note: this uses a mobile ticket, so it’s simple once you’re set up on your phone. And since it’s near public transportation, you’re not completely boxed in if you’re coordinating with another plan around Sydney.

Stop in the Southern Highlands: two wineries, about two hours, and room to choose lunch

The day begins in the Southern Highlands and centers on boutique cold-climate wineries. You’ll spend about an hour at each place, with 2 included wine tastings total across the two wineries.

That structure is ideal for first-timers and repeat wine people alike. Two tastings gives you enough variety to compare styles without turning the day into a blur. You’ll also get a chance to slow down and look around beyond just the tasting counter, since these are boutique wineries rather than high-volume stops.

There’s also an option to have lunch at the first winery. If you take it, you’ll stay in the “wine and settle in” mode before moving on to historic towns. If you skip lunch, you’ll have a lighter start to the next segment and can treat lunch as a planned pause later in the day.

What to watch for in your own planning: because each winery visit is roughly an hour, you should think about pacing your purchases. If you plan to buy bottles, give yourself time to pack and keep the day comfortable, especially with the 10-hour duration.

Berrima’s historic town hour: tasting again, plus optional pub beer

After the Highlands winery time, you head to Berrima, a historic village dating back to the 1830s with colonial-era character. This is where the tour breaks up the wine focus and gives you an actual town hour.

You’ll get another included wine tasting during your time there, then you have optional beer tasting at the local pub. That option is a good match for groups with mixed interests. Wine people get their tasting, and beer fans have a path that does not derail the schedule.

Berrima is also the kind of stop where timing works in your favor. One hour gives you enough time to walk around, look at shopfronts, and pick a spot to relax without feeling rushed. Since the tour is private, you can tailor the balance between wandering and “we’re back in the car soon” based on your group.

Practical tip: if your group has one person who prefers quiet strolling and another who wants snacks or a drink, use your driver to split the difference. Ask what’s worth the extra few minutes and where you can get comfortable without cutting the day too short.

Bowral browsing time: shops, antiques, and an easy break

Bowral is described as the financial center of the Southern Highlands and one of the larger towns in the region. That matters because it’s not just photo stops. You get genuine time to meander through local shops.

You’ll have about an hour here. Depending on your mood, you can look at retail, work in an afternoon tea break, or visit an antiques center. This is one of those stops that can make or break a day for people who don’t want every hour centered on alcohol.

I like that the tour doesn’t force a single plan. An hour in a town like Bowral lets different personalities coexist. The wine-focused person can recover with a calmer pace, and the shop-and-sip crowd can treat it like a planned browse.

If you’re deciding between optional food and shopping, be strategic. If you plan to do lunch earlier at a winery, use Bowral for browsing and a lighter snack. If you skipped lunch at the first winery, Bowral becomes a strong spot to fit in your afternoon break.

Bendooley Estate Book Barn: books, cafe time, and optional tasting

Next up is Bendooley Estate Book Barn, a 30-minute stop that blends books, a cafe, and wine tasting in one place. Even if you’re not a book buyer, it’s the kind of stop that feels different from a straight winery or a straight town.

Because the tasting here is optional, this works well in two scenarios:

• You already feel your group has had enough wine, and you just want a reset with coffee and browsing
• Your group wants one more tasting without committing to a longer winery visit

In practice, 30 minutes is not much time. So I’d treat this as a “select and enjoy” stop. Pop in, see what catches your eye, grab a drink if it fits your day, and move on before you feel rushed.

This stop also adds texture to the overall itinerary. After Berrima and Bowral, it’s a change of pace that keeps the day from feeling like back-to-back drinking and driving.

Mittagong optional brewery tasting near the end (Wed to Sun)

The day can include a final segment in Mittagong, mainly for optional beer tasting at a boutique brewery. This is time permitting, and it’s marked as available from Wed to Sun.

I see the value here as simple: it gives your group a fun closing act if you still have energy. After a long day of tastings and walking around towns, a beer tasting can feel like the lighter, casual follow-up rather than a second round of wine.

Also, beer tasting itself is not included in the main package. So you’ll need to decide on the day whether it’s worth adding cost. If your group is already happy with the two included wine tastings, you can skip the beer and just enjoy the last town time.

Who should book this private Southern Highlands tour, and who might skip it

This is a great fit if you want:

• A private day with only your group up to 7 guests, so you can move at your pace
• A structure that covers both wine and charming towns, not just winery hopping
• Two included wine tastings plus optional lunch and optional beer for extra flexibility
• Comfortable transportation in a Mercedes V-Class, with pickup offered

You might want to skip it if:

• You’re trying to keep costs down and do not value private transport
• Your group dislikes long day trips, since it runs about 10 hours starting at 8:00 am
• You prefer zero options and a perfectly fixed schedule, with no “choose lunch here, add beer there” decision points

Should you book this tour?

If your idea of a perfect day is calm, private, and balanced, I’d say yes. This tour is built for people who like their wine with breathing room, then want real time in places like Berrima and Bowral, not just quick stops. The included tastings mean you start the day with a clear plan, while the optional lunch and beer tasting let you match the day to your own appetite.

If you’re a couple or a small group, do the math based on what you’d pay for a comparable private driver plus tastings. If that total feels right, book it and enjoy the fact that you get a luxury vehicle, a personal driver, and a route that gives you both wine and town life in one long, satisfying day.

FAQ

What time does the tour start?

The tour starts at 8:00 am.

How long is the tour?

It runs for about 10 hours.

How many people are in the group?

It is a private tour/activity with only your group participating, up to 7 guests in a Mercedes V-Class.

What’s included in the price?

You get a private driver in a Mercedes, bottled water, and two included wine tastings for all guests over 18.

Is lunch included?

Lunch is not included. There is an option for lunch at a historic pub and also an option to stay for lunch at the first winery.

Can I cancel and get a full refund?

Yes. You can cancel up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the start time, the amount paid is not refunded.