Traverse the Southern Highlands Wine Trail, where you’ll sample the region’s cool-climate drops at more than 60 vineyards and 15 cellar doors, such as Centennial Vineyards, Bendooley Estate, Mount Ashby Estate, and so much more. The grape juice at Centennial Vineyards is crafted on site, made from a wide variety of grapes planted across 80 acres. Drop by the rather grand cellar door to try them for yourself – it’s open 7 days from 10.00am. visitsouthernhighlands.com.au/trip-ideas/wine-trail

Sitting on the main drag in Bowral is The Press Shop, a beloved fixture when it comes to all-day eateries. Grab a cup of Gabriel Coffee, alongside a hearty morning meal, with a menu that ranges from salmon eggs benedict to butterscotch pancakes. instagram.com/the_press_shop

Quench your thirst for something stronger than coffee at Eden Brewery. The independent craft brewery boasts a growing range of beers made in-house, ranging from IPAs to porters. Drop by the industrial-style brewery to sip their creations, which serves up pub grub and live music alongside. edenbrewery.beer

On the outskirts of Bowral is Berrima, where one of the region’s best restaurants reside. Eschalot is a family-run celebration of local produce – in fact most of it is grown on-site in their kitchen garden. Almost as eye-catching as the fare is the historic homestead in which the eatery sits. eschalot.com.au

Indulge your sweet tooth at pastry haven Gumnut Patisserie. Owners Tracy and Vicki Nicki are award-winning pastry chefs devoted to their freshly baked treats. Think sugar and plenty of it, from elaborate cakes to buttery baked goods (croissants included). gumnutpatisserie.com.au

Named after horticulturalist Sir Harry Veitch, who sought out exotic plants from faraway lands for his wealthy London clients, Harry’s on Green Lane is a fun and quirky setting for a meal in Bowral. The restaurant is brimming with greenery, wicker chairs, marble tables, bookshelves stocked with antique reads and travel memorabilia. harryswinebarbowral.com

Pop by Raw and Wild, an organic and whole food market and cafe in Bowral for a bite to eat. Their market sells certified organic fruit and veg as well as wholefoods, local produce and pantry staples. rawwild.com.au

Located a short walk from Bowral’s main street, the family owned and operated Onesta Cucina dishes up traditional Italian cuisine with a focus on local produce. onestacucina.com.au

Sleep in style at the suave Osborn House nudging Bundadoon. This boutique hotel may be housed in a heritage build, but inside you’ll find a modern escape dreamt up by former SOHO House Design Director Linda Boronkay. 22 lavish rooms are joined by a spa, resident restaurant, bar, and even fireside feasts. osbornhouse.com.au

If you have a soft spot for the historic, make yourself at home in the countryside manor that is the Berida Hotel. An easy stroll to Bowral town centre, the accommodation option is as convenient as it is charming, with 42 rooms sitting within manicured grounds complete with tennis court. The hotel’s on-site restaurant, Bistro Sociale, is also a must whether you’re a guest of the hotel or staying in town. beridahotel.com.au

Or enjoy a self-contained stay at the suavely styled Saint Eloi Studio. This Airbnb offering in leafy Chisholm Hill may be a single bedroom but it’s far from cramped – think French-inspired getaway armed with a fully equipped kitchen and clawfoot bath. airbnb.com.au

Reflecting the style and elegance of the original homestead, Peppers Craigieburn was originally built in 1887 and welcomed its first guests in 1909, with 2009 marking 100 years of exquisite stays, service and food. The venue is set in an area renowned for its national parks, antique shopping and cool climate wines ultimately offering an idyllic and relaxing escape.peppers.com.au/craigieburn

Park Proxi Gibraltar Bowral is the largest hotel and event centre in the Southern Highlands. Inspired by Mount Gibraltar, the 78 luxurious rooms comprise 40 square metres and feature exclusive signature beds providing absolute comfort for a relaxing retreat. parkproxibowral.com

Open everyday from 10am – 5pm, Dirty Janes is a unique marketplace where 90 individual sellers pedde all manner of retro, vintage, antique and artisan-made finds. dirtyjanes.com

Ngununggula, meaning ‘belonging’ in the traditional language of the Gundungurra people, is the first regional art gallery in the Southern Highlands. Ngununggula is a place for creativity, learning and the discovery of the arts for all generations. ngununggula.com