Make an easy escape to the Southern Highlands for fine wines and good times. Just over an hour’s drive south of Sydney Airport (or 1.5 hours by train), it’s the closest wine region to the city, renowned for its cool-climate drops. Learn about the region’s wine-making history — stretching back to the 1870s — as you tour the region’s cellar doors, with nearly 20 to choose from. Pinot noir and pinot gris are specialties, but this region produces extremely memorable wines across the spectrum. Here are some highlights as well as some delicious diversions.  

Seek out local cellar doors 

Indulge your love of pinot noir and pinot gris at Centennial Vineyards in Bowral. Learn more about the cool-climate winemaking process on a tour or simply enjoy a tasting, then move into the cosy restaurant for a sumptuous, seasonally driven meal or high tea — pair your finger sandwiches and scones with a glass of Centennial sparkling or rosé for a special treat.  

Laze on the lush green lawns in summer or warm up beside a crackling fireplace in winter at pinot pioneer Artemis Wines’s rustic cellar door in Mittagong. Sit back, relax and go with the flow by choosing an hour-long tasting of finely crafted wine and spirits at this family-run winery. Visiting on the weekend? Mop up the vino with a crispy woodfired pizza.  

Sip pinot noir, shiraz, riesling, chardonnay and more at PepperGreen Estate, which operates its cellar door and restaurant from an historic Berrima building. Take your pick from a range of experiences, from a guided tasting to a wine and canapes experience, or perhaps a wine and dine experience with a two- or three-course lunch. Seize the opportunity to sample the estate’s premium extra-virgin olive oil while you’re there.  

Discover how Tractorless Vineyard got its name (hint: it involves sheep) on a walking tour of the biodynamic vineyard, also in Berrima, before sampling its sustainably produced wines. Or drop into its tasting room at The Mill in central Bowral for a self-guided sampling of six wines, or a guided tasting of the estate’s entire range.  

Be wowed by the modern design of the cellar door at Bendooley Estate, overlooking the vineyards just outside Berrima, where tastings are available daily. As the sun goes down, this picturesque venue morphs into Leo’s by Night, one of the region’s newest dining destinations. Or enjoy a more relaxed contemporary lunch at the estate’s cosy Book Barn Restaurant featuring a spectacular library on any day of the week.  

Fuel up for another day of wine tasting and local produce 

The type of café you’ll never want to leave, the Burrawang General Store is set in a character-filled building dating from 1867. Soak up Burrawang’s streetscapes from the verandah, cosy up by the fireplace, or linger over high tea with fresh scones and house-made jam in the flower-filled gardens.  

Savour the flavours of the region at Birch, a fine-dining restaurant in Moss Vale that heroes local produce, whether that’s carrots from the kitchen garden or pork from a nearby farm. Tuck into a two or three-course dinner, or book ahead to experience the signature six-course degustation served Thursday to Saturday. Elevate your meal with considered wine pairings. Then head to the venue’s newest addition, Birch Store, also on Moss Vale’s pretty Argyle Street, to stock up on gourmet local produce and homewares.  

Look forward to a true paddock-to-plate experience at Eschalot, housed in a quaint stone cottage in Berrima. Enjoy produce plucked from the venue’s own garden in the beautifully plated contemporary dishes. 

Rediscover a historic Berrima gem at Berrima Vault House, an 1844 convict-built sandstone inn reborn as a stylish venue combining food, drink, luxury accommodation and a private members’ club. Feel like a VIP dining at its contemporary restaurant, open to non-members on the weekends, with dishes designed to be enjoyed with the finest wines from around the region.  

If you’ve visited Moonacres Kitchen in the small town of Robertson, where the casual menu celebrates homegrown and ethically-sourced local produce, you’ll love the group’s new sister-venture, Hearth. Taste the freshness of the flavour-packed seasonal produce that drives the menu of this café next to Ngununggula, the Southern Highlands regional gallery, in Bowral.  

Sleep in style 

Feel like the lady or lord of the manor at Moss Manor, a new boutique hotel experience set in a two-storey building in Moss Vale originally developed in the 1890s as the local mayor’s residence. Soak up the magnificent character of the building with its high ceilings, comfortable lounge areas and secret courtyards during your stay in one of eight individually styled rooms. Each room is hung with contemporary artworks curated by Campbell Robertson-Swan of Sydney’s Defiance Gallery. And revel in luxury extras including wine tasting on arrival, afternoon tea, and a two-course breakfast. 

Embrace the playful, English countryside-esque elegance of Osborn House, a 22-room boutique hotel surrounded by serene bushland and lush gardens in Bundanoon. Treat yourself to a suite with four-poster bed, double shower and speakeasy-inspired minibar, enjoy verdant views from a garden suite, or embrace the bohemian vibe of the cabin rooms with timber-panelled walls, log-burning fireplace and outdoor bath. Enjoy the convenience of dining in at the hotel’s two on-site restaurants, George’s and Dinah’s; George’s Bar is open for afternoon drinks — featuring local wines — from 3–6pm daily. 

Gather your favourite people for a memorable getaway to Vine Lodge in Exeter, where three interconnected buildings dating from 1826 have been lovingly restored into accommodation for up to 14 people. Soak up the historic property’s original charm while enjoying modern conveniences including hydronic heating, WiFi and contemporary kitchen and bathrooms. Relish the simple pleasures of feeding the chooks, meeting the alpacas, and picking your own vegetables from the garden between exploring the region’s wineries and historic villages.