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A Romantic Weekend Guide to the Southern Highlands

With its rolling hills, cool-climate vineyards, grand estate homes, and villages dripping in history, the Southern Highlands really knows how to turn on the charm. An hour-and-a-half from the city, this cluster of country towns is an easy and elegant choice for a couple’s getaway. You can do absolutely nothing, or do it all, and find out just why the Highlands is a foodie destination, shopping hotspot, and natural wonder all at once.

Here’s our guide to a romantic stay in the Southern Highlands.

For a romantic weekend in the Southern Highlands, be sure to…

Tuck into a hearty breakfast at The Courtyard Café in Berrima

If you’re kicking off your weekend in Bowral, pop into Ludo or The Press Shop, a seriously chic café-slash-couture stationery store.

Indulge in a pastry at Flour Water Salt, Bowral’s baking connoisseurs

Have more of a savoury tooth? Try its gourmet pies, or a slice of its signature sourdough slathered with your topping of choice. In Kangaroo Valley? Southern Pies will sort you out.

Be culture vultures with a wander through The Milk Factory

It's a cute, contemporary art gallery down the road in Bowral. The shop sells resin jewellery and glass pieces, if you’re on the hunt for homewares.

Adorn your walls with art from The Rabbit Shack

In Berrima, the gallery has a range of gorgeous photos and artworks, many of which depict the lush landscapes of the Southern Highlands.

Have high tea at Dirty Janes in Bowral

Or at least stop in for the fluffy, homemade scones with a dollop of fresh cream. Afterwards, check out the range of retro homewares and vintage furniture.

Stroll through Corbett Gardens

Sitting pretty in Bowral, the beautiful gardens are best known for their colourful tulips – and shine brightest during the region’s Tulip Time Festival in September.

When lunchtime rolls around, dig into Italian delights at Onesta Cucina

The family-run restaurant uses the freshest local produce, so each dish is as delicious as the next. 

Pack a picnic and walk to Mt Gibraltar Reserve

At 864 metres, it’s the highest point between Sydney and Canberra, and the views are epic. Pick the lookout you like best and flop over on the grass.

Bendooley Estate, Berrima
Bendooley Estate, Berrima
Buy some stories at Berkelouw Book Barn in Berrima

It's a book lover's haven – teeming with new, second-hand, rare and antiquarian books. Halcyon Bookshop in the Kangaroo Valley is on the smaller side but has some great finds. 

Crack open a beer at Surveyor General Inn

Built in 1834, it’s Australia’s oldest continuously licensed inn – if those walls could talk! The best seats are in the beer garden, so cosy up together as you watch the local wildlife. 

Refresh and dress for dinner at Feast at Berrima.

A go-to for comfort food, the restaurant is intimate, making it perfect for date night. It’s licensed but as a BYO option – which is brilliant if you’ve spent the afternoon at a local vineyard. 

Book a table at Eschalot, a fine dining restaurant tucked inside a heritage-listed stone cottage

If you’re celebrating a special occasion, opt for the deliciously decadent seven-course degustation menu, which comes with matching wines. 

Recover with yum cha

On Saturdays and Sundays, head to Zen Oasis on the outskirts of Berrima for yum cha. The vegetarian venue is rustic, relaxed and truly idyllic, thanks to its setting on 100 acres of manicured gardens and koi ponds.

Treat yourself to dessert at Gumnut Patisserie

With pastries and cakes this good you will be lining up for a taste of the goodness at this Bowral institution.

Stock up on lollies (and cue your inner child) at Lolly Swagman

Make your vacay even sweeter with a trip to this Berrima store. It’s bursting with nostalgic treats, like homemade fudge, jawbreakers, and liquorice.  

Peruse the handmade goodies at The Little Hand-Stirred Jam Shop

The shelves of this quintessentially Berrima shop are piled high with jams, chutneys, pickles, and sauces, so the two of you can take the taste of country life home. 

Before you leave, make some time to visit…

Bendooley Estate

In Berrima, this vineyard is both a wine and book lover’s idea of heaven. In the Book Barn, the restaurant serves up country comfort food like charcuterie boards, woodfired pizzas and braised lamb, all perfectly paired with Bendooley wines.


Perhaps the Highlands most iconic (and hatted) eatery, this fine dining venue plucks produce straight from the region’s vegetable growers, dairy and livestock farms. To amp up the romance, go for the ten-course tasting menu, then embrace the food coma in one of the rooms upstairs.

Morton National Park

Lace up your sneakers and bushwalk through the national park until you reach the cascading Fitzroy Falls. If you’re an active couple, keep the theme going with a wander to Fairy Bower Falls, or tackle the Berrima River Walk, a historic trail along the Wingecarribee River.

Glow Worm Glen

From December to February, glow worms take over the Bundanoon part of Morton National Park. Start the walk at twilight, and you’ll see the creatures putting on a twinkling light show. It’s a pretty magical experience.

Gibraltar Hotel Bowral Golf Course

Do you and your partner love to golf? This 18-hole course is as picturesque as it gets. When you’re done, grab a cocktail at Harvey’s Bar.

Milton Park Country House & Spa

Make your romantic getaway even more memorable with a pamper session at the Wellness Day Spa. The couple’s massage will have you both melting into the bed. 

Bendooley Estate, Berrima
Bendooley Estate, Berrima

Romantic stays…

Baynton Cottage

Perched near Mt Gibraltar, this designer retreat is the perfect hideaway. Whether you’re snuggling up in front of wood-burning fireplace, or lounging by the pool and herb garden, there’s no real reason to leave.

Berkelouw Estate Cottages

Part of Bendooley Estate, they have one-, two- and three-bedroom cottages, all decked out with plush, French provincial furnishings. It’s quaint and charming, and best of all, walking distance to the vineyard.

Peppers Manor House

The Highlands is steeped in history, and this 140-year-old hotel will give you a taste of the elite lifestyle. It’s home to the chef-hatted Katers Restaurant and a golf course.

Old Bank Hotel

In Mittagong, this building was a bank in the 1880s, and is now a luxe boutique hotel. There are just five rooms, so you won’t have too much company, plus a lounge and library downstairs, and the piece de resistence: a restaurant and wine cellar in the former bank vault.

Milton Park Country House Hotel & Spa

If you're after a complete luxe and indulgent weekend then you need to check-in to Milton Park. The beautiful day spa aside, the hotel is set in a grand mansion and surrounded by a sprawling manicured garden, you will never want to leave.