The South Coast in winter? Oh, it’s magic. Think: crisp ocean air, moody cliff walks, whales leaping offshore, and a table waiting with good wine and a slow-cooked feast.
Whether you're a nature chaser, a food lover, or a live music fan, winter is the season that brings the best of the region without the crowds. Here’s what’s new, what’s iconic, and why you should book that getaway now.
1.South Headland Walk
Hot off the walking trail! The newly openedSouth Headland Walkin Ulladulla is a stunning way to soak in the dramatic coastline. Hugging the headland with views for days, it’s an easy route for all fitness levels and the perfect pre-brunch stroll.
Pair it with a detour to Warden Head Lighthouse for a chance to spot migratinghumpback whales(peak season is June to November).
2.A Menu Made for Winter Feasting
Cupitt’s Estate’s new winter menu is bringing the warmth. Expect wood-fired local seafood, handmade pastas, rich, earthy sides, and new cold-season pizzas. It’s bold, shareable and completely built to pair with our wine list.
Can’t decide? Book a Long Sunday picnic, La Tavola or Pasta e Vino night and let us curate it for you. See all ourwinter offersand new menu
3.Merrick Watts Live at Cupitt’s
We’re thrilled to be hostingMerrick Watts’comedy showAn Idiot’s Guide to Wine Volume 2this season. His show last year sold out so quickly we decided to host this event on both Friday and Saturday it combines stand-up laughs with a curated tasting of Cupitt’s and guest wines. You’ll experience wine like never before: funny, fun, and a little bit feral.
4. Seriously Good Winter Surf
Let’s be honest, winter is prime time for surfing on the South Coast. The swell is consistent, the wind conditions are often ideal, and the line-ups are blissfully uncrowded. Whether you’re chasing barrels at Rennies, logging at Mollymook’s north end, or paddling out at Dolphin Point, there’s a wave for every level. Just pack your steamer and some post-surf appetite, we’ll have the pizza and beer waiting.
5.Hike, Bike, and Breathe It In
Cooler temps mean longer days outside. The Budawang Ranges offer awe-inspiring hikes, with landscapes rebounding from bushfire and bursting with resilience. Or hit the Woodburn MTB park if mountain biking is more your thing, where adrenaline meets eucalyptus.
6.Whale Watching with Wine
Winter is whale-watching season on the South Coast and we reckon the best way to do it is with a Cupitt’s wine in hand. Grab a bottle of wine, head to the clifftops around Warden Head for a front-row seat to the annual humpback migration. Don’t worry if you forget binoculars, the views (and breaching whales!) are unforgettable.
Want to make a day of it?Shoalhaven’s Wine and Whales Trailpairs coastal lookouts with cellar door stops, making it the ultimate winter weekend plan.
7.Off-Peak = On Point
No crowds. Easy parking. Cosy fireside hangs. Winter on the South Coast is your chance to slow down, reconnect, and get a little bit spoiled. Stay in a vineyard villa, sip wine by the fire, and let the season reset you. We have a special offer for you, ourGourmet Getaway Escape,inclusive of villa stay, breakfast, lunch or dinner and wine tasting for 2 just $499.
