7 Winter Road Trips South Of Sydney You’ll Wish You Did Sooner

We’ve driven every stretch of the NSW South Coast in winter and, honestly, it’s one of the best times to explore this region!

First, no summer crowds fighting for car parks in Kiama, Jervis Bay, or Bateman’s. Amazing local food and produce in Berry, Milton, and beyond.

Plus whales breaching just offshore, that you can swim with!

There’s heaps to do along this coast in winter, so if you’re ready to get out of Sydney, here are the top winter road trips to explore this region!

1. Grand Pacific Drive (NSW)

• Duration: 2-3 days
• Best time: May-October
• Vehicle: 2WD
• Good for: Sydney weekenders after an easy coastal escape with iconic landmarks and guaranteed whale sightings

This is THE gateway road trip from Sydney that actually delivers on the hype!

You’ll go through the Royal National Park beaches, the iconic Sea Cliff Bridge, Wollongong’s epic surf culture, and Kiama, where the blowhole shoots water 20 metres high.

You’ll also want to pull into whale watching platforms every chance you get, as they migrate through these waters from May through November.

Finish in Berry for the most amazing food! It’s a beautiful, quirky town. We were tempted to move there permanently!

Highlights

• Royal National Park coastal track, one of Sydney’s most stunning day walks with beaches, clifftops, and rock pools you’ll have mostly to yourself in winter.
• Sea Cliff Bridge, the 665-metre clifftop bridge where you’re literally driving over the ocean with waves crashing below.
• Kiama Blowhole, Australia’s largest natural blowhole that launches ocean spray up to 20 metres into the air.
• Berry village, a proper country town packed with quality cafes, vintage shops, and the famous Berry Donut Van that’s been slinging fresh cinnamon donuts since 1997.

Here’s every stop on this Sydney to Berry road trip including the best spots for whale watching and hidden beaches worth pulling over for!

2. Kiama to Kangaroo Valley Loop

• Duration: 2-3 days
• Best time: June-August
• Vehicle: 2WD
• Good for: Couples chasing moody rainforest scenery with cosy pubs and waterfalls after winter rain

Winter rain turns this loop into something straight out of a film.

Waterfalls are absolutely pumping and the rainforest is lush as hell! And the country pubs with open fireplaces are the perfect place to end your day.

The Kangaroo Valley Road winds through proper temperate rainforest, drops you into a valley surrounded by sandstone escarpments, then climbs back up to Fitzroy Falls.

Do this anticlockwise, so you’re descending into the valley. The views are much better!

Highlights

• Fitzroy Falls, an 81-metre waterfall with multiple lookout platforms where you can feel the spray from the viewing deck after decent rain.
• Kangaroo Valley village, a small town with a historic suspension bridge, riverside picnic spots, and the Friendly Inn pub that’s been serving locals since 1897.
• Minnamurra Rainforest, 1.6 kilometres of elevated boardwalk through subtropical rainforest where you’ll see lyrebirds scratching around beneath tree ferns.
• Cambewarra Lookout, a 10-minute detour off the main road where you get panoramic views across the entire valley and out to the coast.
• Jamberoo Pub, classic country pub with a fireplace, counter meals, and that proper old-school Australian pub atmosphere you can’t fake.

3. Jervis Bay Winter Whale Weekend

• Duration: 2-3 days
• Best time: May-November
• Vehicle: 2WD
• Good for: Families and wildlife lovers after guaranteed whale encounters and pristine white-sand beaches without summer crowds

Jervis Bay is legitimately one of the best whale watching spots on the entire east coast.

The bay’s sheltered waters mean humpbacks cruise in close to shore, and the Cape St George Lighthouse gives you front-row seats to their migration without needing a boat tour.

You can also see fur seals hanging out at Steamers Beach, pods of dolphins surfing the waves at Hyams Beach, and water so clear you’ll want to snorkel it! Just bring a wetsuit before dipping into the cold water.

Plus, Booderee National Park stays open year-round and those white-sand beaches are dead empty from May to September.

Highlights

• Cape St George Lighthouse, a 5-minute walk from the car park where you’ll watch humpback whales breach and breach again just offshore between May and November.
• Hyams Beach, officially holding the Guinness World Record for whitest sand in the world and home to a resident pod of bottlenose dolphins.
• Booderee National Park, Aboriginal-owned land with empty beaches, bushwalking tracks, and some of the clearest water on the NSW coast.
• Huskisson waterfront, the main hub with cafes, bakeries, and boat charter companies running whale watching tours if you want to get out on the water.
• Steamers Beach seal colony, a rocky headland where Australian fur seals lounge around year-round and completely ignore the occasional swimmer nearby.
• Greenfield Beach campground, first-come first-served beachfront camping inside Booderee where you wake up to kangaroos grazing outside your tent.

Check our detailed Sydney to Jervis Bay weekend road trip guide if you’re keen. It covers every beach, campground, and whale watching spot worth hitting along the way!

4. Mollymook, Milton and Ulladulla

• Duration: 2-3 days
• Best time: May-September
• Vehicle: 2WD
• Good for: Foodies and couples chasing quality restaurants, local wine, and upscale coastal escapes without Sydney prices

The food and wine along this stretch is so good it should be illegal.

Bannisters at Mollymook has Rick Stein’s only Australian restaurant (100% recommend going), while Milton village is crammed with antique shops and bakeries worth queueing for (Milkhaus Cafe was one of our faves).

Not to mention the local oysters. Bec’s not a big fan, but they’re some of the best she’s ever tasted anywhere in NSW!

As for wineries, there’s heaps to choose from! Cupitt’s Estate is great and GWYLO has an epic selection of wines as well.

Highlights

• Bannisters by the Sea, upscale accommodation with Rick Stein’s restaurant serving the freshest local seafood and ocean views from every table.
• Milton village, heritage-listed main street packed with cafes, the famous Milk Haus Cafe, and antique stores in 1800s buildings.
• Mollymook Golf Club, clifftop course where you’re dodging kangaroos on the fairways and watching whales breach between holes from May to November.
• Ulladulla Harbour, working fishing port where you buy oysters straight off the boats and watch the commercial fleet unload their catch each afternoon.
• Burrill Lake, massive estuary perfect for kayaking, stand-up paddleboarding, and catching fish without dealing with ocean swells.

5. Batemans Bay and Murramarang

• Duration: 3-4 days
• Best time: May-September
• Vehicle: 2WD
• Good for: Families with kids and caravan travellers wanting reliable wildlife encounters and sheltered beaches perfect for slower-paced exploring

Batemans Bay is one of the best destinations in all of NSW.

The beaches are protected and the caravan parks are right on the water! Plus, the kangaroos hopping along Pebbly Beach at sunrise is like something out of a tourism ad.

The nearby Murramarang National Park is epic as well, with incredible hiking, empty surf breaks, and beachfront camping at Depot Beach.

And if you’re travelling with little ones, there’s Mogo Zoo just inland where they can feed giraffes!

Highlights

• Pebbly Beach kangaroos, a resident mob of eastern grey kangaroos that lounge on the sand and let you walk within metres for photos.
• Depot Beach campground, beachfront national park camping where you pitch your tent 50 metres from the water.
• Broulee Island walk, a 30-minute loop around a rocky island connected by sand spit where you’ll spot seals, seabirds, and rock pools teeming with life.
• Batemans Bay Bridge, the viewing platform at the south end gives you panoramic views over the river mouth and is prime whale watching territory in winter.
• Observation Point Lookout, a scenic coastal vantage point offering panoramic 360-degree views of Batemans Bay, Snapper Island, and the Tollgate Islands

Check out our full Sydney to Batemans Bay road trip with every wildlife hotspot, beach, and campground mapped out for the perfect coastal escape!

6. Narooma, Tilba and Bermagui (NSW)

• Duration: 3-4 days
• Best time: May-October
• Vehicle: 2WD
• Good for: Wildlife photographers and nature lovers chasing close encounters with fur seals, little penguins, and seabirds you can only access by boat tour

Barunguba (Montague Island) is an incredible nature reserve near Narooma, and it’s one of the main reasons to do this road trip.

You can visit it by booking a boat tour like this one.

This will give you access to the island, which is absolutely packed with Australian and New Zealand fur seals, little penguin colonies, and over 90 bird species!

But the surrounding towns are worth exploring as well.

The coastal walks around Narooma are seriously underrated for winter whale watching. Central Tilba is heritage-listed and looks identical to how it did in the 1890s, and Bermagui overdelivers with its quality seafood restaurants.

Highlights

• Montague Island boat tour, the only way to access this nature reserve where you’ll get within metres of 1,000+ fur seals, little penguin burrows, and massive seabird colonies.
• Central Tilba village, an entire town heritage-listed from the 1890s gold rush era with original timber buildings, craft shops, and the ABC Cheese Factory still making cheddar by hand.
• Bar Rock Lookout Narooma, wheelchair-accessible platform where you watch humpback whales, dolphins, and seals cruising past the headland between May and November.
• Bermagui Blue Pool, ocean rock pool carved into the rocks where locals swim year-round and you can snorkel with luderick and drummer fish.
• Glasshouse Rocks, a cluster of wave-sculpted rock formations accessible at low tide where you’ll find rock pools, caves, and nesting shearwaters.
• Wagonga Inlet, sheltered estuary perfect for kayaking and stand-up paddleboarding when the ocean is too rough for beach swimming in winter.

7. Sapphire Coast Whale Road Trip (NSW)

Duration: 3-5 days
Best time: May-November
Vehicle: 2WD
Good for: Serious whale watchers and road trippers who want to end at Australia’s whale capital with wild coastal scenery and historic whaling towns

Eden was a whaling town until 1930, humpbacks migrate through Twofold Bay from May to November.

The historic Killer Whale Museum tells the wild story of Old Tom, the orca that helped whalers hunt baleen whales in exchange for the tongues.

Beowa National Park protects rugged headlands, empty surf beaches, and coastal walking tracks that give you front-row seats to whale migration without another person in sight.

Green Cape Lighthouse marks mainland Australia’s 2nd most southern point and whales cruise past the rocks below all winter long.

Highlights

• Eden Killer Whale Museum, the skeleton of Old Tom the orca who hunted alongside whalers and the wild true story of orca-human cooperation documented from 1863 to 1930.
• Twofold Bay whale watching, protected waters where humpbacks linger for days during migration and boat tours get you close enough to hear them breathe.
• Green Cape Lighthouse, Australia’s 2nd most southern mainland lighthouse with dedicated whale watching platforms where you’ll spot breaches, tail slaps, and spy hops from May to November.
• Beowa National Park, newly created park protecting 30 kilometres of wild coastline with cliff walks, hidden beaches, and almost zero tourists even in peak season.
• Merimbula Lake, massive estuary with oyster leases, pelican colonies, and calm water perfect for kayaking when the ocean is too rough.
• Pambula Beach, long stretch of sand backed by dunes where you can walk for hours, spot dolphins surfing the breaks, and camp right behind the beach at Pambula Beach campground.

The South Coast in winter is genuinely special. Empty beaches, whale sightings from your car window, and that crisp coastal air that makes you feel alive.

Pick a trip, pack the thermals, and get out there. Trust us, you won’t regret swapping crowded summer beaches for moody winter coastlines and the best wildlife encounters NSW has to offer.