From staying in a heritage cottage surrounded by national park to fossicking at a farmers’ market for seasonal produce, or heading out to sea on a whale-watching cruise, here’s how to do winter in Sutherland Shire.
Sutherland Shire locals were not surprised when Tourism Australia crowned Bate Bay’s beaches as the best in the country in 2026. And while the boardshort and bikini brigade have Cronulla on their radar each summer, in winter these stretches of sand offer something else entirely.
Mooch around the Shire Farmers’ Market
There’s a particular pleasure to be had in wandering around the Shire Farmers’ Market on a cold winter’s day, coffee in hand, in no particular hurry. Bring your eco bag to fill with fresh sourdough from the Sonoma stall before drifting over to Cheese on Wheels and one of the many fresh produce stalls. Reward your efforts with a brekkie burger from Farmgate to Plate. Expect a fleet of food trucks at the weekly event, held at the Flora Street car park in Sutherland every Saturday from 8am to 1pm, rain, hail or shine.
Enjoy a fireside feast at Jensens
A fireplace changes the entire feel of a winter feast. At Jensens, you settle in, the warmth wraps around you like a hug from your nan and you start to greet people like you’re in a Hallmark movie. Dining out in winter is not the time for restraint. Recommendations for indulging in a fireside feast with the family include the confit duck legs, Black Angus eye fillet, and fried gnocchi with whipped cacio e pepe cream. Stay longer than you planned nursing a neat nip of 12-year-old Chivas Regal.
Sweat it out in a sauna
There is nothing quite like indulging in a sauna in the cooler months. It’s winter wellness done properly. Head to Bath Haus to sweat it out and emerge feeling like you’ve done a full reboot on mind and body. Infrared saunas combine soothing heat with rejuvenating LED light, each colour enhancing relaxation and recovery. This synergy helps ease joint pain, muscle soreness and conditions like arthritis while supporting scar tissue healing. The light therapy treatments are also known to boost mental wellbeing. You can also combat Seasonal Affective Disorder (SAD) with an infrared treatment at La Cure in Caringbah.
Simpson Cottage, Bundeena
Simpson Cottage is in Bundeena, which is blanketed in bushland at the edge of Royal National Park. Described in Condé Nast Traveller’s roundup of the 77 best vacation rentals in the world as “the ultimate refuge”, this three-bedroom heritage stay offers the rare combination of genuine solitude and supreme comfort. There’s no agenda beyond what you make of the day – which, in a place this beautiful, might involve venturing to Audley Dance Hall Cafe for brunch, paddling into Cabbage Tree Basin with Bundeena Kayaks or simply sitting in the sunshine with a good book.
Croydon Lane or Blind Bear
The best small bars have a way of making you feel like you’ve got the inside running from the moment you walk in. Croydon Lane Wine & Tapas Bar, The Blind Bear and Duke’s After Dark all share that quality. While you could stay on the couch binge-watching the latest true crime doco to drop on Netflix, these intimate, cosy, considered bars are the kind of places that will make you fall in love with the season.
Go on a whale-watching adventure
Through to November, humpback whales move through the waters off the Shire on their great migration north to warmer waters. And they are not subtle about it. A breach seen from the headland, or from the deck of a whale-watching cruise, is the kind of experience that recalibrates your sense of scale in an instant.
Winter in the Shire offers a lot of good things. But this might be the best of them with Cape Solander considered one of the best places in Sydney to spot whales.
The trails around Bundeena
Winter paints the Australian bush in a honeyed light, rendering the landscape in a soft palette of sage green and cinnamon. Pull on your Tevas to complete the coastal track that winds out from Bundeena through the Royal National Park. Or set off on a clear winter’s morning to trek from Cape Solander to Cronulla. While you’ll pass the odd hiker, it will, at times, feel like the path belongs entirely to you. Pack layers, take your time, and let the landscape open up to clifftop views that stop you mid-stride. The Shire is laced with a network of beautiful trails.
Carla Grossetti is a local journalist who writes for publications such as Luxury + Travel, delicious., Australian Traveller, International Traveller and Escape. Follow @food.travel.stories on Instagram to enjoy Carla’s food and travel adventures around the world.
