If sleepy beach town is what you’re after, Pearl Beach is for you. There are no fancy hotels here. This small beach town on the Central Coast is beloved by locals and regular holiday-makers who relish slow days on the beach and sunset downers at seaside venues like Amalfi Restaurant & Bar.

We can’t think of a better way to spend a day than basking in the sun at the sparkly new Terrigal Pavilion, drink in hand. The multi-faceted 760-seater ‘Pav’ is divided into three distinct venues that will match your tribe and vibe: The General Store, The Tropic and pavilion. You can also watch the waves kissing the shore from your table at nearby Meribella at the Crowne Plaza Terrigal Pacific. Coco Bar & Dining offers an altogether more casual vibe, while Yellowtail is about refined seafood dining. Keep it light, bright and breezy over pizza at Rhonda’s.

The city that meets the sea is home to a luxurious Crystalbrook Collection hotel, Kingsley, and QT Newcastle. It also serves up a plethora of fine dining options, nightclub hotspots, unique local pubs and great cafes. Don’t miss Three Monkeys for its famed generous breakfasts and awesome coffee, take a trip down foodie Darby Street to let your eyes do the eating. For a low key long lunch or dinner by the beach, make sure you check out Parry St Garage and the coolest addition, Light Years. Meanwhile, there’s the Civic Theatre, City Hall, Nobby’s Beach, Merewether Beach, the Newcastle Baths and the city’s iconic Bogey Hole to keep the nature lovers entertained.

Just 2.5 hours from Sydney’s skyscrapers, Port Stephens isn’t far from the NSW capital but seems a million miles away. There’s coastal walks, national parks, and plenty of beaches, with Nelson Bay a standout. Spend days swimming at Little Beach Reserve, or viewing Gan Gan Lookout, and evenings dining waterside at Little Beach Boathouse.

Just 120 km south of Sydney sits Kiama, the beach town known for cliffside cavers the Kiama Blowhole and Little Blowhole. If you’d prefer to work up a sweat, there’s the 20 km Kiama Coastal Walk, stretching between Minamurra and Werri Beach. Plus plenty of beaches to choose from, like main drag Surf Beach. Once you’ve worked up an appetite in the sea, head to Little Betty’s for craft cocktails, small-batch wines and share plates. For breakfast on-the-go Parfait Patisserie for French bakes goods and Slow Dough for a coffee and to pick up a load of sourdough.

Sitting in Shoalhaven on the South Coast is Jervis Bay. With its crystalline waters paired with bright white sands (most evident at Hyams Beach) this place is certainly easy on the eyes. Throw in a handful of national parks, a lighthouse, and a brewery and you have the makings of a great beachside escape.

Thirroul and neighbouring Austinmer are easily one of New South Wales’ best beach towns. Especially if you’re a coffee fan – after all, this beachside stretch nudging Newcastle is home to an impressive number of outstanding cafes. But it’s not just beach and coffee, Thirroul hosts plenty of boutiques to peruse, and sits on the stunning Grand Pacific Drive.

A definite contender for Australia’s prettiest town, Orange is well-worth a visit on any weekend. A 3 hours drivefrom Sydney, Orange is a food and wine lover’s paradise. Choose from plenty of wineries and cellar doors, you can find our top picks here. If you’re after a private, curated food experience, look no further than Country Food Trails. Founder Nicole Farrell is an experienced international tour guide and a local, so she knows where to find the best of everything. Aesthetes will adore chic retail establishments like The White Place, Hawkes General Store and The Sonic, and there’s plenty of top notch restaurants and bars — like newcomer Hey Rosey, Mr Lim, and The Schoolhouse — to keep your belly full and your tastebuds tingling. Love coffee? Head to Good Eddy for the best. And make sure you visit nearby Millthorpe, which is a burgeoning food and wine hub in its own right. If you’re looking to treat yourself to a luxurious stay, look no further than Basalt. Plan your trip here.

South Coast darling Milton has long been loved for its places to eat and drink. Garden-to-plate eatery Milk Haus, housed in a former cheese factory, is arguably its most famous venue and for good reason. But there is more to see and do (and eat) here; snack plates and specialty wines form the heart of Small Town Provisions, while the flavours of the Middle East have shaped the menu of more recent addition Nomah. Then there’s Bar Yuki, a jazz-playing record space with Japanese dishes, and local taphouse, The Milton Hotel. If it’s wine you have a soft spot for, Milton has that too. Cupitt’s Estate is an easy drive away, and offers wine-tasting tours, a sophisticated onsite restaurant, as well as accommodation in a handful of intimate villas.

It’s a favourite for a reason. Not only is the Hunter Valley very close to Sydney, it’s also home to Australia’s oldest wine region. There’s some 150 cellar doors, 60 plus eateries and at least four hatted restaurants. There’s everything from cheese, chocolate, beer and gin to the region’s world-famous aged Semillon and delicate, complex reds. Gourmet must-visits include Muse, Bistro Molines, Margan Restaurant and EXP. For the vino lovers, there’s non-stop cellar doors, including Brokenwood, old-school Tyrrell’s Wines, biodynamic and organic fave Krinklewood, Margan, Briar Ridge and bastion of the new wave of Hunter Valley winemakers, Usher Tinkler Wines.

Just north of Newcastle, Port Stephens is an easy 2.5 hour drive from Sydney. Boasting beautiful beaches, exquisite restaurants, abundant national parks and plenty of coastal walks, it’s an easy long weekend escape or short break. There’s everything from fine dining to fish and chips on offer, with plenty of fresh, local produce like avocados, stone fruit, figs and macadamias to inspire the local chefs. Rick Stein’s Bannisters Port Stephens just one of the must-visits, and his new luxury hotel is an ideal place to stay. As well as the Bannisters restaurant, there’s also the Bannisters pool bar, and a cute nearby pub known as The Cheeky Dog. Among the other notable eateries, Terrace Bar, Lil Buddha, Moby’s and The Point. If you’re travelling from Sydney, make a point to stop in at Saddles in Mount White.

Mudgee may not be as well known as the Hunter Valley, but when it comes to history – and damn good wines – this slice of NSW is punching well above its weight. The landscapes are breathtaking, vineyards and olive groves as far as the eye can see. On a sunny morning, a footpath table outside Market Street Cafe is hard to beat. Head to the Alby + Ethers for hearty breakfasts, lunch and coffee. For a rustic winery lunch, you can’t go past Di Lusso Estate for graceful Italian varietals and great woodfired pizzas. Make sure to stop by the Mudgee Brewing Company for fine, handcrafted ales and good quality, beer-friendly food. Pipeclay Pumphouse serves up plenty of incredible local produce with a seasonal menu and locally focused wine list. There’s plenty of amazing cellar doors to visit, including Logan Wines, Lowe Wines, Robert Stein and Mudgee’s first winery, Robert Oatley Vineyards. When it comes to accommodation, Sierra Escape is a truly unique glamping experience that combines nature and luxury.

Any closer to the beach you would be paddling for a wave alongside long-time local Pam Burridge, who has a surf school in the town of Mollymook. Rick Stein and his eponymous eatery, Rick Stein at Bannister’s, has helped put the pretty South Coast spot on the map. It’s fair to say this restaurant with rooms is worth the mooch to Mollymook for fresh local seafood. Dust the sand off your feet at South Molly Beach and saunter into Salt and Spencer for light bites, live music and cocktails. Go to Gywlo for Asian-inspired street eats punched up with spice

Just under two hours’ drive from Sydney, the slew of lush accomodations offerings in this country town prove it’s a hot spot for Sydneysiders. For art-deco-meets-contemprary-design head to Berida Hotel, which is found in a private residence built in 1925, and for country charm there’s no better than Peppers Craigieburn Bowral. Ardour Milton Park has just undergone a multi-million dollar renovation and will reopen with a all-new dining concept we can’t wait to try. But it’s not all luxury stays. Bowral is known for its antique shopping and incredible international food offering, also. Fine-dining Thai dishes are plated up at Paste, while Leila’s at the Grand serves up modern take on traditional Lebanese food.

An oldie, but a goody. Most Aussies can recall a family trip or two to Berry. Approximately two hours from Sydney, this country town ticks all the boxes. After good wine? Head to the award winning cellar door and vineyard, Silos Estate, or Two Figs. Want to take in the country while kicking back on a luxurious estate? There’s Linnaeus Farm for that. Keen to taste some delicious Aussie produce? South on Albany source local food cooked with a European twist. And if you have a sweet tooth, you can’t leave Berry without a stop at The Famous Berry Donut Van, which has been serving up deliciously fresh cinnamon donuts since 1964.