Tucked between Milton and Ulladulla, Cupitt’s Estate is where you come to unwind and leave feeling like you’ve been welcomed into the family.
This breath-taking property, surrounded by rolling vineyards and the Shoalhaven’s Budawang mountain ranges, houses an eco-friendly, family-run winery, a cellar door, a five-star farm-to-table restaurant and ten architecturally designed luxury villas. There’s even a pet-friendly wine garden, so you can linger a little longer over your vino, without having to leave your four-legged companion behind.
We spent 24 hours at this idyllic country retreat, uncovering the stories behind the estate, indulging in culinary bliss, tasting six of the winery’s newest varietals, and exploring every corner of the vineyards, villas, and hidden gems that make Cupitt’s Estate so unforgettable.
A Family Legacy in the Shoalhaven
Rosie and Griff Cupitt hail from the Southern Highlands, where they owned and operated the well-known Bowral Hotel while raising their two boys. The couple are well-versed in wine, thanks to their passion for European vintages and extensive travel throughout the region; with Rosie even leading tours in the South of France that included stops at 28 wineries, from the Northern Rhône to Bordeaux.
In 2003, they stumbled across a beautiful patch of countryside in the Shoalhaven. They knew the region well, having owned a holiday home in Narrawallee since the 1980s. The plan was simple: buy a property near the beach house where they could retire comfortably, perhaps grow some grapes, and run some cattle.
The plans quickly escalated when sons Tom and Wally, along with daughter-in-law Libby, joined the picture. What had started as a quiet retirement project soon became a shared family vision: introducing European-inspired varietals to the region to perfectly complement the South Coast’s already relaxed way of life.
Sometimes the best outcomes come from the plans you never made — just ask Wally Cupitt, Rosie and Griff’s youngest.
Wally took over as Chief Winemaker in 2013. Initially, his interests lay elsewhere; he had a passion for beer, spending his time brewing at home or gaining work experience at Four Pines Brewery. But after a life-changing trip to France, where he met his mum’s winemaking mentor, Alphonse, he discovered a love for wine. And as they say…the rest is history.
While the Cupitts strongly value the traditional French and Italian methods of wine-making, their philosophy is progressive. They work with fruit grown locally at the Estate whilst also sourcing from New South Wales’ most respected cool-climate wine regions: Hilltops, Tumbarumba, Orange, and the Canberra District. The goal? To follow flavour over formula to create expressive, balanced and highly enjoyable wines.
Tasting the Terroir
Cupitt’s Estate won gold in the wineries, distilleries and breweries category at the prestigious 2024 NSW Tourism Awards and with good reason! We took a tour of the winery, led by Libby and Wally Cupitt, to learn about the winemaking process, from harvest to bottle.
Along the way, we were treated to a tasting straight from the barrel: wines cloudier in appearance, brighter in acidity, and less refined on the palate, but already showing plenty of promise.
We then ventured to the underground cellar for a private tasting of the estate’s signature wines in their final form, beginning with a medium-bodied, crisp Vermentino and finishing with a voluptuous Montepulciano, layered with notes of blackcurrant and cherry, and a subtle lift of spice and tannin. It felt like a tastebud tour from Sardinia to Tuscany.
Cupitt’s offers wine tasting experiences at the cellar door, as well as more immersive tours that include a stroll through the vineyard and a behind-the-scenes look at the winemaking process. There’s also a “meet-the-maker” experience, where you can learn about winemaking firsthand while enjoying a cheese and wine pairing in the underground cellar.
Stay in Style
While the history and love of winemaking alone would be enough to convince you to visit this beautiful property, the luxury on-site accommodation is what’s going to entice you to stay.
Ten highly private, architecturally designed villas are purpose-built for relaxation.
Outdoor baths and picturesque views invite you to fully switch off, breathing in the fresh country air as your worries melt away. From the balcony, cows graze in the distance while kangaroos bound past, bringing the landscape to life.
The interiors are just as soothing – natural colour palettes extend the outdoors indoors. The white robes and king bed beckon after a busy day of tasting wine.
For bigger groups, there’s on-site farmhouse accommodation as well – a spacious, four-bedroom, open-plan home with an outdoor pool that can house up to eight guests.
Paddock-to-Plate Perfection
Whether you’re visiting for the day or staying on-site, a visit to the paddock-to-plate Dining Room will perfectly round out your day.
Open for lunch and dinner, the restaurant has a seasonal menu that highlights the exquisite produce from the Estate and the local coastal region. The Kingfish Crudo and Grilled Yamba Prawns were absolute standouts and the Burrata paired with Chardonnay fennel jam and house-baked focaccia was a revelation, perfectly balancing the creamy texture with fresh, vibrant flavours that showcase the best of Cupitt’s Estate and the South Coast’s seasonal bounty.
Ryan Smith has recently been appointed Executive Chef, bringing more than 27 years of international culinary experience to the South Coast. His career spans fine dining kitchens in Sydney, including Banc and Restaurant Balzac, as well as London, where he has cooked at events for the British Royal Family. Need we say more?
The estate is entirely eco-conscious: produce is grown on-site, served in the restaurant, and any scraps or leftovers are returned to the compost and worm farm, closing the loop on the estate’s food journey.
The warmth of the staff really shines through here as well. If you’re lucky enough to have Sophie as your waitress you’ll be well looked after!
Celebrations and Cellar Finds
There’s often live music for the locals – with visitors always warmly welcomed. Sunday sessions bring rhythm to long afternoons relaxing in the wine garden and Friday Sunset Sessions are the perfect way to unwind after a long week with feel-good eats and grooves from 5pm.
If you’re looking to take a piece of Cupitt’s home with you, you can purchase wines directly from the cellar door, online or at select venues across New South Wales.
Cupitt’s Estate leaves an impression. It’s more than a winery; it’s a place where family, flavour, and the South Coast lifestyle come together in perfect harmony.
One visit, and you’ll understand why so many return, eager to experience the warmth, the wine, and the story behind this unforgettable estate.
