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Why hundreds are flocking to this hideaway outside Sydney for a dreamy slice of Tuscany: 'The perfect weekend reset'

Why hundreds are flocking to this hideaway outside Sydney for a dreamy slice of Tuscany: 'The perfect weekend reset'

Daily Mail​7 days ago
If there's one destination that delivers no matter the season, it's the NSW South Coast.
And tucked away just outside the charming town of Milton lies a hidden gem that feels more like Tuscany than regional Australia, is Cupitt's Estate.
A short drive from Ulladulla and Mollymook's stunning beaches and only a few hours from Sydney, this award-winning family-run winery, brewery, restaurant, and boutique accommodation offers a truly unforgettable escape.
Cupitt's Estate began over 18 years ago when Rosie and Griff Cupitt purchased a 75 hectare farm overlooking the Budawang Ranges and Burrill Lake, with the dream of growing grapes and crafting their own wine.
That dream has since blossomed into a thriving estate now run by the next generation Libby and sons Tom, and Wally.
Today, the property seamlessly blends rustic charm with modern luxury. From the moment you arrive, it's clear this is a place that embraces a true farm-to-table philosophy.
The restaurant is a true highlight, set in a stylish yet relaxed dining room with floor-to-ceiling views
The estate produces its own wine, beer, and seasonal produce, much of it showcased at their restaurant, where you'll find a menu that's both refined and regionally inspired.
Think fresh house-made cheeses and charcuterie, woodfired pizzas, and vibrant dishes featuring ingredients straight from the garden.
For a more relaxed experience, you can enjoy a glass of wine on the deck or settle in for a tasting at the cellar door.
The estate produces its own wine, beer, and seasonal produce, much of it showcased at their restaurant, where you'll find a menu that's both refined and regionally inspired.
Don't miss the Nebbiolo, a personal favourite.
Start your visit at the cellar door, where you can sample the estate's impressive range of wines. Whether you prefer a crisp Chardonnay or something bolder like their elegant Nebbiolo (a standout), the tastings are guided by passionate staff who clearly love what they do.
Downstairs, the wine cave offers a rare behind-the-scenes look at the winemaking process - rustic barrels and stainless-steel tanks silently working away.
Cupitt's also boasts the longest-running craft brewery in the Shoalhaven region, pours a diverse lineup of handcrafted beers. Each brew reflects the same care and commitment to quality as the wines, with rotating taps showcasing IPAs, lagers, pale ales, and seasonal specialties.
Accommodation at Cupitt's takes the experience to the next level. The architecturally designed villas are spacious and minimalist, with eco-conscious touches throughout. Each villa includes a lounge and dining area, kitchenette, and a private deck - but the real showstopper is the freestanding outdoor bathtub.
The luxury Villas offer boutique accommodation with private outdoor baths
We were taken for a tour of the wine cellar beneath the restaurant
Watching the sun set over the rolling hills with a glass of bubbles in hand (from the outdoor tub, naturally) was a highlight of my stay so much so, I took two dips in one night.
The minibar is one of the most thoughtfully curated I've seen, filled with locally made treats, Cupitt's own wines, and even pre-mixed cocktails from the estate's bar.
A welcome breakfast hamper adds to the sense of relaxed luxury.
Whether you're here for a romantic weekend, a winter retreat, or a summer escape, Cupitt's delivers.
And while Milton may not be on everyone's radar, those in the know will tell you that autumn and summer are some of the most beautiful times to visit.
What truly sets it apart is its authenticity. Nothing feels overly polished or artificial; instead, the entire estate radiates warmth, integrity, and a deep connection to the land and local community.
Whether you're here for a tasting, a long lunch, or an indulgent weekend away, you'll find yourself wanting to stay just a little longer.
nd it's one you'll be talking about long after the last glass is poured.
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