A 3-day itinerary in the Southern Highlands

Morning 

Set out early from Sydney and you’ll be in Bowral in time for brunch. The Press Shop is a local favourite, set inside a beautiful heritage building that also houses a boutique letterpress studio. The menu heroes local produce and features inspired dishes like breakfast potato gnocchi, prawn toast and panna cotta.  

Bespoke Letterpress, Mittagong

Afternoon  

This little village punches above its weight when it comes to style, so grab a coffee to go and set out to explore some of Bowral’s excellent shops. Along Bong Bong St you’ll find chic boutiques like MicMac Boutique, Hem, ARKKE, Zoë Georgiou and Carousel Lifestyle. For homewares and vintage finds, wander over to Dirty Jane’s and the adjacent Green Lane precinct. If you are feeling peckish, check out Harry’s on Green Lane, a quirky eatery brimming with greenery, wicker chairs, marble tables, bookshelves stocked with antique reads and travel memorabilia.  

Load your purchases into the car and set off for the 15min drive south to your hotel, Moss Manor, in the village of Moss Vale. A grand Georgian building dating back to 1890, the house was once the mayor’s residence and was transformed into a luxurious boutique hotel in late 2022. There are just eight rooms, all with charming original features, opulent furnishings and contemporary artworks. 

Moss Manor, Moss Vale - Credit: Moss Manor

Evening 

Take a short stroll down to the main street of Moss Vale tonight for dinner and drinks at Southern Highlands Brewing Taphouse. Order a crafted-locally beer flight alongside a Brasserie-style menu of steals, burgers, pastas and popular mainstays such as pork ribs, garlic prawns and lamb kofta. On the way back to your hotel, drop in to Wine Mosaic Lounge for a glass of something local on one of the comfy couches.

Southern Highlands Brewing Taphouse, Moss Vale - Credit: Elise Hassey | Southern Highlands Brewing Company

Morning 

Wake up early this morning and explore some of the natural wonders that surround the Southern Highlands. Mount Gibraltar is a short drive from your hotel and the highest point between Sydney and Canberra. Reaching 863m high, the mountain is a 150-million-year-old collapsed volcano, and is threaded with walking trails and spectacular lookouts. Refuel with breakfast at The Shaggy Cow cafe in Mittagong; the sourdough pancakes with caramelised bacon makes for a sweet start to the day. 

St Maur Wines, Exeter

Afternoon  

This afternoon, it’s time for wine. There are more than a dozen cellar doors dotted throughout the Southern Highlands, specialising in cool climate drops like pinot noir, pinot gris and rosé. Because of the compact nature of the area, all the wineries are within an easy drive (though you’ll have to choose a designated driver). Popular cellar doors include Bendooley Estate (also home to the famous Berkelouw Book Barn), PepperGreen Estate, St Maur, Southern Highland Winery and Tractorless Vineyard, where petite, black-faced sheep keep the grass down between the vines. 

If you’d prefer to let someone else handle the details, book a wine tour with The Highlands Tour Co. Every tour is private and can be customised to take in exactly what you want to see – and taste. 

Tractorless Vineyard, Berrima

Evening 

Finish the day at the one-of-a-kind Berrima Vault House. Inspired by London members’ clubs like Soho House, this convict-built former pub has been reborn as a cosy place to drink, dine, work and play. But don’t worry – you don’t have to be a member to drop in for dinner on a Friday or Saturday night. The menu is eclectic, covering everything from kombu tofu to BFC (Berrima fried chicken), lobster rolls and vegan strudel, but the real fun is the people watching. It’s a hot spot for local celebs and Sydney society visiting their country retreats. 

Berrima Vault House, Berrima

Morning 

Enjoy a sleep in this morning, making the most of your last few moments in the supremely comfortable bed at Moss Manor. Then grab coffee and a French pastry at Les Gourmandises, a chic bakery cafe on Bong Bong St in Bowral. Then it’s off for a morning of art at the innovative Ngununggula the Southern Highlands’ first regional art gallery, which opened in late 2021. It was championed by legendary Australian artist (and Southern Highlands resident) Ben Quilty and occupies the former dairy shed at the 1880s Retford Park. The name means ‘belonging’ in the local Indigenous language and features works from artists like John Olsen and Ken Done, a collection of Aboriginal art, and a vibrant exhibition program. 

Ngununggula, Southern Highlands - Credit: Zan Wimberley

Afternoon  

There’s just time for one more long lunch as you make your way back to Sydney. Centennial Vineyards is just outside of Bowral and the on site restaurant is one of the best in the Highlands. Owner and head chef Robin Murray focuses on seasonality for his menu, so you could sit down to a rich, slow-cooked beef bourguignon in winter or a broad bean tart with red pepper coulis and zucchini flower in spring. Chef Murray also has a small farm nearby where he grows fruit and vegetables, and raises animals to serve in the kitchen. 

Centennial Vineyards, Bowral

Getting there: 

The Southern Highlands is around 90 minutes’ drive south of Sydney. You can also catch the train directly from Sydney to Bowral, which takes around two hours. Once you’re in the Highlands, all the villages are within a 30min drive.  

Cafe Bike Shop, Bundanoon