You can leave Sydney early and arrive in Bowral just in time for brunch. The Press Shop, a local favorite, is located in a heritage building that also houses a boutique letterpress studio. The menu is based on local ingredients and includes dishes such as breakfast potato gnocchi and prawn toast.


Bowral is a small village that packs a punch when it comes to style. Grab a coffee and explore the shops. You’ll find stylish boutiques along Bong Bong St, including MicMac Boutique and Hem. Other shops include ARKKE. Carousel Lifestyle is also located here. Browse Dirty Jane’s for vintage and homewares. You can also check out Harry’s Green Lane if you’re hungry. This quirky eatery is filled with greenery and wicker furniture, marble tables, antique books, travel memorabilia, and a lot of other interesting things.

Load up your purchases in your car and drive 15 minutes south to reach your hotel, Moss Manor, located in the village of Moss Vale. The house, a grand Georgian mansion dating back to 1890 and once the mayor’s residence, was converted into a luxury boutique hotel at the end of 2022. The eight rooms are all decorated with original charm, luxurious furnishings, and contemporary art.


Take a stroll to Moss Vale’s main street tonight and enjoy dinner and drinks in Southern Highlands Taphouse. You can order a locally crafted beer flight along with a Brasserie menu that includes burgers, pasta, and mainstays like pork ribs. Wine Mosaic Lounge is a great place to relax with a local drink on the couches.


Day Two Key Facts:

Mount Gibraltar can be found at:

  • Oxley Drive Bowral, 2576
  • Moss Manor is a 13km (17min) drive away


Explore the Southern Highlands early in the morning. Mount Gibraltar, the highest point between Sydney and Canberra, is just a short drive away from your hotel. The mountain, which is 863m tall, is an ancient 150-million-year-old collapsed volcano. It is also threaded with spectacular lookouts and walking trails. Breakfast at the Shaggy Cow in Mittagong is a great way to start the day. The sourdough pannacottas are topped with caramelized bacon.


It’s wine time this afternoon. More than a dozen wineries are located in the Southern Highlands, and they specialize in wines from cool climates like pinot noirs, pinot griss, and roses. All the wineries can be reached by car, but you will need to designate a driver. The most popular cellar doors are Bendooley Estate, PepperGreen Estate, St Maur Winery, Southern Highland Winery, and Tractorless Vineyard.

Book a wine tour through The Highlands Tour Co. if you prefer someone else to handle the details. Each time is tailored to your specific tastes and interests.


The Berrima Vault House is a unique place to end the day. This convict-built, former pub, inspired by London’s members’ clubs such as Soho House, has been transformed into a cozy place to dine, drink, work, and play. You don’t need to be a club member to come in on Friday and Saturday nights for dinner. The menu is diverse, with everything from BFC (Berrima Fried Chicken) to vegan strudel and lobster rolls. But the best part is watching the people. The place is a popular hangout for Sydney society and local celebrities visiting their country homes.

Day Three: Celebrate the Arts

Day Three Key Facts:

Ngununggula can be found at:

  • Bowral, 2576
  • Moss Manor is located 11km away and takes 14 minutes to drive.


You can enjoy a good night’s sleep this morning in Moss Manor’s incredibly comfortable bed. Grab a coffee and a French pasty at Les Gourmandises, a chic bakery café on Bong Bong St, Bowral. After a delicious breakfast, enjoy a morning at Ngununggula, the Southern Highlands’ first regional art gallery. It will open in late 2021. Ben Quilty, a Southern Highlands local and legendary Australian artist, was the driving force behind the project. It occupies a former dairy shed in Retford Park from the 1880s. The name, which means “belonging” in the local Indigenous languages, features artworks by artists such as John Olsen and Ken Done and a vibrant exhibit program.


You’ll have time to stop for a long lunch on your way back to Sydney. Centennial Vineyards, located just outside Bowral, has one of the Highlands’ best restaurants. Chef Robin Murray, the owner, focuses his menu on seasonality. For example, you might enjoy a rich beef bourguignon with red pepper coulis in winter or a broad-bean tart in spring served with a zucchini flower and a red pepper coulis. Chef Murray has a farm in his backyard where he raises and grows vegetables and fruits, as well as animals for the kitchen.

How to get there

Southern Highlands are located about 90 minutes south of Sydney. Trains run directly from Sydney into Bowral in around two hours. All the Highlands villages are within 30 minutes of each other once you arrive.

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