Sydney Wine Tasting & Southern Highlands with Pick up & drop off

A day of cool-climate wine is a good plan. This private Southern Highlands run from Sydney mixes wine tastings at top cellar doors with a calm, guided pace, all handled by Kookaburra Sydney Tours. You’ll hit Bowral and Berrima, with the guide name Joey getting called out as a real highlight for making the day feel smooth and fun.

I especially like that the tastings are included, so you can focus on sipping, asking questions, and actually enjoying the vineyards. I also like the structure, four winery stops plus a one-hour lunch window in Bowral, without rushing you around. The main drawback to keep in mind is that lunch and any bottles you buy are not included, so plan extra spending if you want to take wine home.

Key Highlights at a Glance

• Private guide and vehicle means you get a tailored pace for your group, not a squeeze through a shared bus.
• Tastings are included at every winery stop, so you know what you are paying for.
• Bowral and Berrima give you two classic Southern Highlands bases, with different vibes day to day.
• Four winery stops keep the day varied, including a boutique small-batch producer at the end.
• About 8.5 hours total with a return drive to Sydney CBD of around 1.5 hours, so plan this as a full-day outing.

Why Southern Highlands Wineries Work So Well From Sydney

Southern Highlands wine touring is one of those rare “easy logistics, good payoff” day trips. The region is only about 1.5 hours from Sydney’s CBD by road, which means you can leave the city feel behind without committing to an overnight trip. That is a big deal if you want a full experience but still want your evening back in Sydney.

Also, this part of New South Wales is known for cool-climate wines, and this tour leans directly into that style. You visit wineries that are built around that approach, so you are not spending the day guessing what you will like. If you enjoy crisp whites, balanced reds, or anything that feels more focused and less sweet, this is a strong match.

The tour is private, so the day can feel more like a guided country outing than a stop-and-scan checklist. And when the guide is doing the job well, it changes everything, Joey is specifically mentioned as excellent in the feedback tied to this experience.

Price and Value: What $283.31 Gets You (and What It Doesn’t)

At $283.31 per person, you are paying for more than wine samples. The price covers a private guide plus the vehicle, and it includes wine tasting at each winery stop and bottled water during the day. That matters because transport is often the hidden cost in wine days, especially when you want pickup and drop-off in Sydney rather than DIY driving.

It also means you should be able to taste through the day without calculating what each stop costs. For many people, that is the difference between a fun wine afternoon and an awkward budget scramble.

What is not included is lunch, and any bottles you buy to take home. So if you want a sit-down meal and a souvenir bottle or two, you should budget for that upfront. The one-hour lunch window in Bowral gives you options, but the tour itself does not cover the tab.

Pickup, Timing, and How to Plan for an 8.5-Hour Day

This tour runs about 8 hours 30 minutes total. You should treat it as a full-day schedule, not a quick excursion. The good news is that the return drive to Sydney CBD is listed as 1.5 hours, and your guide drives you back to where you are staying.

The timing is also structured around short, clear blocks at each stop. The first three winery visits are about 1 hour each, the Artemis stop is shorter at 45 minutes, and then you have a 1-hour window for lunch in Bowral before heading back.

That pacing is practical. It gives you enough time for tastings and questions, but it also avoids the “too long, too tired” trap. Still, this is a day with drinking, walking around cellar doors, and car time, so plan around it. I’d bring a light layer, since country air can feel different than the city. And if you are sensitive to alcohol, slow down during tastings so the last stop does not feel like a blur.

The Private Guide Factor: Joey and a More Relaxed Pace

A private tour is not just a nicer label. It changes how the day flows. With your own group and a dedicated guide plus vehicle, you are not fighting for space, not waiting on other people’s late arrivals, and not getting rushed through tastings.

The feedback tied to this tour specifically highlights Joey as an excellent guide who took the group to incredible wineries. That kind of guide can do two things at once: make the tasting experience more fun and make the logistics painless. In a wine region day, that’s what you want. You want to show up, taste, learn something real, and leave without worrying about where to park or how to time everything.

You should also use the guide time wisely. Ask what to try based on your preferences, and if you like something, take notes so you can remember it when you see bottles later. That turns a tasting day into a personal shortlist, not just memories.

Stop 1: Centennial Vineyards in Bowral (About 1 Hour)

The first winery stop is Centennial Vineyards in Bowral. This is where the tour sets the tone: cool-climate wines, scenic countryside feel, and what is described as exceptional hospitality.

You get about 1 hour here, and wine tasting is included. That duration is ideal for most people. You can taste at an easy pace, ask what the winemaking style is like, and still have time to look around without feeling chained to a counter.

Practical tip for this stop: decide early what your taste direction is. If you enjoy crisp and fresh profiles, focus your attention there and let the guide steer you. If you prefer structured reds, you can use the 1-hour window to compare across styles. Either way, Centennial is a strong start because it is framed as both award-winning and welcoming, so you can get comfortable quickly.

Stop 2: Peppergreen Estate in Berrima (About 1 Hour)

Next up is PepperGreen Estate in Berrima. This stop has a different vibe than Bowral. It is in the historic village of Berrima, and the tour description calls out premium cool-climate wines along with sophisticated dining and artisanal experiences.

You get another 1 hour, with wine tasting included. This is a good point in the day to slow down a bit. Berrima tends to feel like a slower, older village, so you get a chance to enjoy the setting while you taste.

Also, this is one of the lunch options later. The tour notes that lunch can be eaten at Pepper Green Estate, Centennial Vineyards, or Bendooley Estate. So if you like the atmosphere here during your tasting, you can plan to return for lunch later in the day if it suits your schedule.

A consideration: if you plan to shop or pick up bottles, keep an eye on how much you end up wanting. The tour includes tastings, but bottles are not included, so you’ll want to be deliberate by the time you hit the midday decision.

Stop 3: Bendooley Estate and Its Georgian-Style Book Barn (About 1 Hour)

Bendooley Estate is next, and it’s a stop with real visual and cultural appeal. The tour highlights a beautifully restored Georgian homestead, an award-winning restaurant, and a world-class vineyard.

You spend about 1 hour here, again with tasting included. This is a strong mid-tour anchor because by now you have your taste preferences warmed up, and you can compare what you liked earlier with what Bendooley offers.

The Georgian homestead angle matters because it changes the feeling of the tasting. You are not just visiting a wine room. You are in a heritage setting with a restaurant presence. Even if you do not linger for lunch here, it helps you understand why people rave about this kind of wine destination. Wine is part of the place, not just the glass.

Lunch planning tip: since lunch can be eaten here, you can aim for a sit-down meal option if you want a proper reset. The tour also notes there are other food choices in Bowral if you prefer something simple like a pub or a casual meal.

Stop 4: Artemis Wines for a Boutique, Small-Batch Finish (About 45 Minutes)

The final winery stop is Artemis Wines. This one is described as a boutique producer crafting small-batch wines, with an emphasis on elegance, balance, and a sense of place.

You get about 45 minutes. That shorter time is not a flaw. It is a smart way to keep the day from dragging once you have already tasted several wineries. It also encourages focus. Instead of trying to do everything, you taste with intention and leave enough time to enjoy lunch and the return drive.

If you like wines that feel refined rather than loud, this is the stop that tends to land well. Artemis is specifically framed around balance, so it is a good choice if you want something that feels like the last word of the day rather than just another tasting flight.

Lunch in Bowral: Eat at the Wineries or Choose Pubs and Hotels

After the four winery stops, you get a 1-hour break in Berrima or Bowral area for lunch, depending on where you choose to eat. The tour info is clear: lunch can be eaten at Pepper Green Estate, Centennial Vineyards, or Bendooley Estate. If you’d rather not stay in a wine setting, the tour also says you can eat in the township of Bowral at other hotels or pubs, with options like steaks, chicken dishes, or pizzas.

This is one of the most useful parts of the schedule because it gives you control. If you want to keep the day “wine-country calm,” pick a winery lunch. If you want variety, go toward Bowral’s food options.

My practical advice: eat something you can enjoy without feeling too heavy. You still have a return drive to Sydney, and you may want to feel human by the time you get back. If you plan to buy bottles, eating a normal lunch helps you decide more clearly. No one makes great choices when their stomach is empty or they are overly tired.

Return to Sydney CBD: 1.5 Hours Where the Guide Does the Driving

Once lunch is done, the day winds down with the return drive to Sydney CBD, listed at about 1.5 hours. Your guide drives you safely to your hotel.

This is a real quality-of-life benefit. After a day of tastings and country roads, you do not want to be navigating traffic or hunting for parking. The tour handles the hard part, so you can relax and get your evening back without stress.

Practical note: if you are buying bottles, think about how you will carry them comfortably. The tour is about the wine experience, but you are still responsible for your purchases. Planning ahead makes the ride back easier.

Who This Tour Suits Best

This is a great fit if you want a straightforward Sydney wine tasting day without the DIY headaches.

It is ideal for:

• Couples who want a romantic cool-climate day with pickup and a private guide
• Small groups or special occasions where you want better pacing than a shared group tour
• Wine newcomers who want structure and guidance, since tastings are included and the day is paced in clear blocks
• More serious wine lovers who like comparing wineries across a tight time window, from award-winning estates to boutique producers

It might be less ideal if you:

• Want a flexible, open-ended day with no set stops, because this schedule is built around specific wineries
• Have tight timing plans for your evening in Sydney, since it is about 8.5 hours total
• Are trying to keep costs super low, because lunch and wine bottles are not included

Final Call: Should You Book This Southern Highlands Wine Tasting Tour?

If you want a well-paced Southern Highlands wine day with pickup and drop-off, tasting included, and a guide like Joey called out as excellent in the feedback, I think it is a strong booking option. The best value comes from the fact that you pay once for tastings plus private transport, then you enjoy the day without constantly doing arithmetic in your head.

I would book it if you are the type who likes a “planned day” but still wants things to feel calm and personal. The itinerary balances several winery styles, including Bowral and Berrima, and it gives you real time for lunch rather than rushing you straight through.

I’d skip or reconsider if you want lunch and bottles included in the price, or if your schedule cannot handle an 8.5-hour commitment.

FAQ

How long is the Sydney Wine Tasting and Southern Highlands tour?

The tour duration is approximately 8 hours 30 minutes.

What is included in the tour price?

Wine tasting is inclusive, and the tour includes a private guide and vehicle, plus bottled water.

Which wineries are visited during the tour?

The tour includes Centennial Vineyards, PepperGreen Estate, Bendooley Estate Book Barn, and Artemis Wines.

Is lunch included?

Lunch is not included. You have a 1-hour lunch break where you can eat at Pepper Green Estate, Centennial Vineyards, or Bendooley Estate, or choose other places in Bowral.

Are wine bottles included to take home?

No, wine bottles for home are not included.

Does the tour offer pickup and drop-off?

Yes, pickup is offered, and the guide drives you back to your hotel when you return to Sydney.

Is this a private tour?

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

Is bottled water provided?

Yes, bottled water is included.

What is the cancellation policy for a full refund?

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