Morning

Set out early from Sydney and you'll be in Bowral in time for brunch. Lucette is a chic new Parisian-style bistro in the centre of town with an all-day menu. Keep things light with a pain au chocolate or croque monsieur or go all out with a classic eggs benedict.

This little village punches above its weight when it comes to style, so grab another coffee to go and set out to explore some of Bowral's excellent shops. Along Bong Bong St you'll find chic shops like MicMac Boutique, HEM, Zoë Georgiou and Highlands Emporium. For homewares and vintage finds, wander over to Dirty Jane's and Suzie Anderson Home in the adjacent Green Lane precinct.

Dirty Janes, Bowral

Afternoon

Bowral is famous for its flowers and though spring is obviously the best time to experience them, make time for a garden ramble whenever you visit. Corbett Gardens in the centre of town is the home of the Tulip Time Festival from mid-September, when more than 80,000 brightly coloured bulbs burst into bloom. Southern Highlands Botanic Gardens captures the seasonal beauty of the region, with cool climate gardens showcasing the rich colours of autumn or winter perennials.

Tulip Time Festival 2018, Bowral

Grab your bags and check in to your stylish home for the weekend, Ardour Milton Park. An elegant country estate just outside of Bowral, the century-old property underwent a multi-million-dollar revamp to reopen in 2026. A mix of heritage grandeur and contemporary cool, there are 44 rooms and suites plus gorgeous restaurants, a cosy bar, and an indulgent spa.

Ardour Milton Park Bowral, Bowral - Credit: Salter Brothers Hospitality

Evening

After a quick refresh, head back into town for an aperitif at Millsheds Bar & Distillery. Producing small batch gin, vodka and liqueurs (and with whisky aging in barrels) you can enjoy them in a cocktail or try the range in a tasting paddle.

Millsheds Bar and Distillery, Bowral - Credit: Merrigangs Distillery and Bar

It's a quick drive to Mittagong for dinner. One-hat restaurant Paste is run by Michelin-starred chef Bee Satongun, who brings her innovative Thai cuisine to the Southern Highlands. Using fresh local produce, she reimagines classic dishes with a distinctly Australian twist for surprising – and delicious – culinary creations.

Paste Australia, Mittagong

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 863 metres high, the mountain is a 150-million-year-old collapsed volcano and is threaded with walking trails and spectacular lookouts.

Mount Gibraltar Heritage Reserve, Mittagong - Credit: Destination Southern Highlands

Refuel with breakfast at The Press Shop, a local favourite set inside a beautiful heritage building that also houses a bespoke letterpress studio. The menu heroes local, seasonal and sustainable produce, with dishes like chai panna cotta and Turkish eggs with mint yoghurt. Afterwards, pick up some gorgeous stationery or a new journal to take home with you.

Bespoke Letterpress, Bowral - Credit: Bespoke Letterpress

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. Popular cellar doors include Bendooley Estate (also home to the famous Berkelouw Book Barn), PepperGreen Estate, St Maur, Artemis Wines, Dawning Day Winery and Tractorless Vineyard, where petite, black-faced sheep keep the grass down between the vines.

PepperGreen Estate, Berrima

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). 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.

Bendooley Estate, Berrima

Evening

Finish your wine tour in Berrima in time for dinner at Eschalot, set inside a heritage building that dates back to the 1840s. It celebrates the flavour of fire, with menus adapted to what's in season around the Southern Highlands. That could mean burrata with eggplant crisps, grilled squid with chorizo and feijoa, Moroccan spatchcock with chilli mandarin jus, or a whole lamb shoulder from Maugers Meats, raised on the farm just outside Robertson. If you're not sure what to order, choose the Feed Me menu and let the chefs do their thing.

Eschalot, Berrima

Morning

Enjoy a sleep in this morning, making the most of your last few moments in the supremely comfortable bed at Ardour Milton Park. Perhaps a swim in the indoor pool or some downtime in the steam room? Make the short drive to Buradoo to visit the newest venture from the Three Blue Ducks team. Set on a 240-hectare regenerative farm, you can wander through the orchards and gardens, and spot livestock in the fields. Grab a few pastries from the artisan bakery and that all important coffee.

Three Blue Ducks, Burradoo - Credit: Kitti Gould

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 Regional Gallery, Bowral - Credit: Brian Rapsey

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.

Centennial Vineyards, Bowral