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

Discover the Best of Southern Highlands on a Wine Tasting Tour from Sydney

If you’re craving a day that combines stunning countryside views with the chance to sample some of New South Wales’ finest wines, this Sydney Wine Tasting & Southern Highlands Tour might be just what you need. While we haven’t taken it ourselves, the glowing reviews and detailed itinerary suggest it offers a well-rounded, authentic experience that appeals to wine lovers, couples, or groups seeking a relaxed escape just outside Sydney.

What we love about this tour is how it balances scenic beauty, quality wine, and ease of access. The small-group, private guide setup ensures a more personalized experience, and the variety of wineries—from boutique producers to historic estates—promises a well-rounded tasting journey. An added bonus is the comfortable door-to-door pickup and drop-off, making logistics one less thing for you to worry about.

That said, a potential consideration is the full-day nature of the tour—at around 8.5 hours, it’s a long day for some. But if you’re comfortable with a full itinerary that includes sightseeing, tastings, and leisurely lunches, this tour offers fantastic value. It’s best suited for anyone interested in a mix of wine, beautiful landscapes, and local food, whether you’re celebrating a special occasion or simply want a taste of the countryside.

👉 See our pick of the 25 Best Guided Tours In Sydney

Good To Know

• Convenient pickup and drop-off from Sydney ensure a stress-free day trip.
• Visit multiple wineries with varied styles, from boutique to award-winning estates.
• Expert guide offers insights and local knowledge, enhancing the experience.
• Inclusive tastings allow you to sample a range of cool-climate wines.
• Flexible lunch options at wineries or nearby cafes cater to different tastes.
• Beautiful scenery and historic charm make it a photo-worthy adventure.

An In-Depth Look at the Tour Itinerary

Starting Point: Pickup and Journey to the Southern Highlands

The tour begins bright and early, with pickup from your Sydney accommodation, usually between 8:00 and 8:30 am. The roughly 1.5-hour drive to the Southern Highlands is comfortable and allows for some light chatter about what to expect. Your guide, likely someone like Joey—who has been praised for his expertise and friendly approach—sets the tone for what’s to come.

First Stop: Centennial Vineyards

Your first tasting session is at Centennial Vineyards in Bowral. This estate is prized for its award-winning cool-climate wines and picturesque setting. You’ll spend about an hour here, enjoying tastings that include some of the best local wines. Reviewers mention the “incredible wineries” visited early on, highlighting that Centennial offers a mix of scenic views and quality wines, perfect for kicking off the day.

Second Stop: Peppergreen Estate

Next, the tour heads to Peppergreen Estate in Berrima, a charming village with a historic feel. This estate blends elegance with artisanal touches, offering a chance to sample premium wines while soaking in the sophisticated atmosphere. The estate is also known for its artisanal experiences and delicious, refined dining options. Guests appreciate the “elegant blend” of wines and the chance to explore a winery that emphasizes both quality and style.

Third Stop: Bendooley Estate Book Barn

Adding a touch of historic elegance, Bendooley Estate combines a Georgian homestead with award-winning food and a renowned book barn. The vineyard and restaurant are top-tier, and visitors often comment on the beautifully restored architecture and lush grounds. This stop offers not only tastings but also photo-worthy moments, making it ideal for those who love combining wine with a bit of cultural charm.

Fourth Stop: Artemis Wines

A smaller boutique producer, Artemis Wines focuses on crafting small-batch wines that embody balance, elegance, and a true sense of place. This is a favorite among visitors who appreciate craftsmanship and attention to detail. The 45-minute tasting allows you to really focus on the subtle nuances of each wine, and reviewers note that Artemis is committed to quality over quantity.

Lunch Break: Flexible Options

Around midday, you’ll have about an hour to enjoy lunch. Options include on-site at Peppergreen Estate or Centennial Vineyards, where you can indulge in local produce and pairing menus, or venture into Bowral’s cafes and pubs for something more casual. Many guests mention enjoying excellent steaks, chicken dishes, or pizzas, making for a relaxed break before continuing your wine adventure.

Final Stop: Artemis Wines and Return to Sydney

After lunch, the tour includes a final visit to Artemis Wines, where you can revisit favorite styles or explore new offerings. Then, it’s a scenic 1.5-hour drive back to Sydney, allowing for a relaxed reflection on the day’s highlights. You can sit back, sip bottled water, and let your guide handle the driving while you take in the views.

Why This Tour Offers Great Value

At $283.31 per person, the tour covers visits to five notable wineries, tastings, private transport, and a guided experience—amounting to a convenient, all-in-one package. The inclusion of admission tickets at each stop guarantees that you won’t face hidden costs or surprises. The private guide and vehicle add a level of comfort and personalization often missing from larger group tours.

While lunch isn’t included in the price, the proximity of excellent local eateries and on-site winery options means you can tailor your meal experience to your tastes and budget. The tour’s flexibility makes it suitable whether you’re a wine novice or a seasoned connoisseur.

Authentic Experiences and Insider Access

Reviewers mention that guides like Joey are not just knowledgeable but also personable, making the day feel more like a chat with friends than a stiff tour. The stunning views, excellent wine selection, and well-curated stops promise a genuine taste of the region’s rich offerings. Participants also appreciate the relaxed pace, which balances tastings with ample time to enjoy the surroundings without feeling rushed.

Who Is This Tour Perfect For?

This tour suits couples seeking a romantic escape, small groups with a shared love of wine, or corporate outings looking for a classy day out. If you appreciate beautiful scenery, boutique wineries, and relaxed yet guided experiences, you’ll find plenty to love here.

Final Thoughts: Is It Worth It?

For anyone wanting to explore New South Wales’ cool-climate wines without the hassle of planning, this tour offers a comprehensive, enjoyable experience. The combination of stunning vistas, high-quality tastings, and expert guidance makes it a standout choice for a day trip from Sydney.

The tour’s structure allows you to indulge in a variety of wines, learn about the region’s winemaking traditions, and enjoy some downtime in scenic settings. The fact that it’s private and customizable further enhances its appeal, ensuring you get a tailored experience.

This trip is especially worthwhile if you’re looking for a luxurious yet authentic outing, with plenty of opportunities for photos, good food, and memorable moments. Whether celebrating an occasion or simply treating yourself, it offers real value and a taste of the best of the Southern Highlands.

FAQs

What is included in the tour price?
The tour includes wine tastings at each winery, a private guide and vehicle, and bottled water.

Is lunch included?
No, lunch is not included, but there are options at wineries or nearby cafes. You have about an hour to eat at your leisure.

How long is the drive from Sydney to the Southern Highlands?
The drive takes approximately 1.5 hours each way, making it a manageable day trip.

Do I need to prepare anything in advance?
Reservations are confirmed upon booking, and since it’s a private tour, you can discuss any special requests directly with the provider.

Are the tours suitable for all ages?
Most travelers can participate, but since wine tasting is involved, it’s best suited for those of legal drinking age.

Can I purchase wine bottles to take home?
Yes, wine bottles can be bought at the wineries for home consumption, but they are not included in the tour price.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. Late cancellations or no-shows won’t be refunded.

How many people are in each group?
This is a private tour, so only your group will participate, ensuring a more personalized experience.

Is transportation provided?
Yes, private transportation is included, and pickup/drop-off is available from your Sydney accommodation.

What if I want a longer or shorter experience?
The standard tour lasts around 8.5 hours, but you can inquire about customizing the timing when booking.

Final Words

For lovers of wine, scenic drives, and exclusive experiences, this Sydney Wine Tasting & Southern Highlands Tour offers a seamless way to explore some of New South Wales’ most esteemed wineries. It combines comfort, expert insights, and authentic regional flavors, making it an excellent choice for a relaxed yet refined day out.

Whether you’re celebrating, entertaining clients, or simply indulging your curiosity, this tour delivers a memorable taste of the Southern Highlands’ viticultural charm. It’s a balanced blend of scenic beauty, boutique wines, and personalized service—perfectly suited for anyone wanting a genuine, hassle-free escape from the city.