Secrets of the Southern Highlands for your next long weekend

At Di Jones we have a love affair with the Southern Highlands and our Sydney team is constantly asking for tips from our Bowral office on the best things to do when you want to spend a weekend in this gorgeous part of the countryside. We thought we’d share some insider tips with you, for your next trip down South.

Lisa-Marie Cauchois made the move from our Wahroonga office to Bowral about 2 years ago, taking her young family with her to live on a gorgeous farm. Attracted by the gorgeous landscape, slower pace and being surrounded by nature, Lisa-Marie is the perfect person to share her Highlands secrets with you.

Your favourite winery
Artemis Wine, 46 Sir Charles Moses Lane, Mittagong
Why you love it: 
Great wine, good food, fantastic events including Yoga, Jazz and Open-air Cinema in the vines!

Fitzroy Falls and Mt Gibraltar

There’s so many! It depends on what you’re looking for, we have it all!
Harry’s on Green Lane (café/wine bar/restaurant) 15-17 Banyette St, Bowral
Harvey’s Bar at Gibraltar Hotel (cocktail lounge) Boronia Street, Bowral
Eschallot in Berrima (Fine Dining) 24 Old Hume Hwy, Berrima
Bistro Officina at Berida Manor (wine & Tapas or fine dining restaurant option) 6 David Street, Bowral
Onesta Cucina (real italian Trattoria-style food but elegant atmosphere restaurant) 5 Boolwey Street, Bowral

Event/time of year: 
We have four true seasons so every season brings out the best in the Highlands! Spring is a beautiful time of year, as we have the Tulip Festival and also the Bong Bong races. There are a lot of open-gardens this time of year as well.

Milton Park Country House Hotel and Spa – 200 Hordens Road, Bowral
Why you love it: 
This is a beautiful getaway if you’re looking for an old-worldly country retreat. They have a day spa and cater for weddings/functions/large groups/families/couples. There is a variety of accommodation options on the property and an award-winning garden!



Sales agent David Meldrum spends his time between Bowral and Beecroft and has over 43 years of experience sampling the delicacies and discovering the best the Highlands has to offer. He’s seen its popularity grown over the last 10 years, and knew it wouldn’t be a secret for too much longer.

Café Rosso, 3 Bowral St & Station Street, Bowral
Why you love it: 
Fantastic pizza and atmosphere

Bendooley Estate, 3020 Old Hume Hwy, Berrima
Centennial Vineyards, Centennial Road, Bowral
Why you love it: 
Views, food, wine – what’s not to love?!

For Highlands Charm: 
Briars Restaurant and Bar, 653 Moss Vale Road, Bowral
Why you love it: 
It’s one of the oldest inns in Australia and has a lovely old fashioned feel.

So book in your next weekend getaway, and while you’re there visit the distinctively Di Jones cottage on Boolwey Street in Bowral, to let the team know what you thought of their picks.