It’s hard to make a choice between Melbourne and Sydney – the two great cities of Australia offer much to eat and drink, and to see and do all year round. Personally, for a girl born and bred in the tropics, Sydney has a slight edge over Melbourne with more hours of sunshine a day throughout the year, especially in the winter months. And for those of you who haven’t been to the Harbour City, or are planning to re-visit after many years, our four-day itinerary (perfect for those long weekends) covers everything from beaches and inner city walks to fine dining and craft beer.

Day 1: Hit the Beach(es)

four days in Sydney

The Terraces in the Kensington Street, Chippendale. Image courtesy of Destination NSW.

If you’re flying in from Singapore or elsewhere in Southeast Asia, it’s likely that you’ll catch the red-eye and arrive late morning to maximise the time you have in Sydney like we did. A taxi from Kingsford Smith Airport to the city centre will likely set you back A$30-40, so if you’re travelling solo, you’d be better off taking the Airport Link, which costs approximately A$18.

four days in SydneyWe put up at The Old Clare Hotel, located in the Chippendale on Kensington Street, and less than 10 minutes away from Central Station on foot. Formerly a working-class enclave, Chippendale has been transformed by gentrification and is currently the ‘it’ neighbourhood of the inner city. If you’re hungry by this time, The Old Clare is home to Automata – its sister restaurant Blackwattle recently opened up on Amoy Street – helmed by Chef Clayton Wells, and serves a three- (A$55) and five course (A$88) lunch menu that champions seasonal produce on Fridays and Saturdays. Alternatively, head to the six-month old Concrete Jungle to revive yourself with a cup of coffee and their visually stunning Blue Majik Smoothie Bowl (A$17.50) made with blue algae spirulina, granola, berries, and toasted coconut flakes. Psst, Kensington Street is also home to KOI Dessert Bar by Masterchef Australia Season 7 contestant Reynold Poernomo.

After lunch, stretch your legs with the Bondi to Coogee Coastal Walk, a 6-km clifftop walking track that boasts stunning vistas of the ocean, cliffs, bays, and rock pools. We suggest starting from the Coogee end so you’ll end up in Bondi for the sunset; if you prefer a shorter experience, start at Clovelly Beach or Bronte Beach. Still early when you get to Bondi? Have a snack at Gelato Messina or Lox Stock and Barrel, then explore the beach suburb with stylish boutiques and cosy art galleries.

four days in Sydney

The Bondi to Bronte Walk. Image courtesy of Destination NSW.

Cap off the first day in Sydney with sundown cocktails at Bondi Icebergs Dining Room & Bar – they have the most photographed ocean pool in Australia – and dinner at Blanca, a charming restaurant armed with a Scandinavian aesthetic and a Mediterranean-meets-Japan menu. Their tasting menu (A$69 for seven courses, A$85 for ten) holds gems like aged raw beef with fresh wasabi mayo on sesame leaf and Saikyo miso Mahi Mahi with yuzu dashi, kale, and asparagus.

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Day 2: Sydney Icons

Start your day in Surry Hills with a hearty brunch. Love ricotta pancakes? Go to Bill’s (the sweet corn fritters are pretty good too). Devon Cafe has one of my favourite brunch plates of all time – Breakfast with The Sakumas see pairs miso grilled king salmon with a smoked eel croquette, and 63-degree egg – while micro roastery Reuben Hills doles out some of the best coffee in the city.

four days in Sydney

Image courtesy of Reuben Hills

Sydney’s city centre is best explored on foot. The distance between Surry Hill and Circular Quay, where the Opera House is located, can be covered in 45 minutes but on the way, stop by to check out Sydney’s Chinatown and see the architecturally splendid Queen Victoria Building (QVB, as the Sydney-siders call it) in the central business district. Cut over to Hyde Park for some greenery en route – it’s Australia’s oldest park and home to some 580 mature exotic and native trees, art works, water features, and monuments like the ANZAC Memorial and the Archbald Fountain.

four days in Sydney

Jacaranda trees in spring bloom at Circular Quay, Sydney. Image courtesy of Destination NSW.

The city disappears into the harbour at Circular Quay, which is also the main ferry terminal in Sydney, moving people to Manly, Watsons Bay, and Taronga Zoo. Most first-timers would be eager to see Sydney’s most recognisable icon up close; the right-hand side walkway that leads to the Sydney Opera House will bring you to the Royal Botanic Gardens as well. However, if you’re feeling peckish, go left at the terminal and walk over to The Rocks for some delish scones at The Tea Cosy or French pastries at La Renaissance Patisserie Francaise.

Prior to the arrival of European immigrants, The Rocks was part of Gadigal land (an Aboriginal clan), and it became the point of entry for most of them from the end of the 1700s. Learn more about the history at The Rocks Discovery Museum or at the marvelous Susannah Place Museum, which was originally a terrace of four houses in 1844. They’ve recreated the 19th and 20th century narrative lived by people in the neighborhood. If you prefer art to history, the Museum of Contemporary Art is a must-visit.

four days in Sydney

Signature Pavlova at Bennelong Restaurant, Sydney. Image courtesy of Destination NSW.

What’s better than see the Sydney Opera House? Eating in it, of course. With celebrated Australian Chef Peter Gilmore at helm, Bennelong‘s culinary offerings (A$140 for a three-course dinner) are culturally significant. You’ll find that only the best of Australian produce and products make Bennelong’s à la carte menu, desserts, and wine list. Reservations are essential for the main dining room on the lower level overlooking the quay. After dinner, stroll over to Bulletin Place for a nightcap. The shoebox of a bar with distressed walls specialises in produce-driven cocktails, and the five-drink strong menu, handwritten on a reel of brown paper, changes daily.

Day 3: Street Art, Culture, and Cocktails

four days in Sydney

Newtown. Image courtesy of Culture Scouts.

Unlike Surry Hills and Darlinghurst, where gentrification has more or less reached its peak, Newtown is still rough around the edges, but it boasts a young (due to its close proximity to University of Sydney), artsy, multi-cultural atmosphere with its street art, quirky boutiques, and diverse dining scene. To see Newtown through the eyes of a Sydneysider, we went on a walking tour with Culture Scouts, which curates tours in the city’s cultural hubs.

four days in Sydney

Continental Deli Bar & Bistro

Starting at the train station at 10am, the three-hour Inner West Tour (A$95, includes a coffee) runs three days a week and shows you a different type of Sydney as it lives and breathes. Besides seeing key pieces of street art in the neighbourhood – the council actually pays graffiti artists to ‘fix’ vandalism – some interesting places we passed or popped into include Holey Moley, a fun 18-hole mini golf course equipped with a bar and kitchen and Lentil as Anything, a restaurant mostly run by volunteers with no set prices as a way to help the underemployed, homeless, and the disenfranchised. There’s also Dresden Optics with it quirky, lightweight nylon frames recycled from bottle caps, beer kegs, and fishing nets, the extravagant selection of buttons at All Buttons, 1950s inspired designs at Retrospec’d Clothing, and independent local designer brands at acquire @ DESIGN.

There’s no lack of food in Newtown either; there’s traditional Turkish Ice cream at Hakiki and regular gelato at Cow and the Moon, while The Stinking Bishops provide the cheese, cold cuts, and wine. Head to Gigi’s Pizzeria for intriguing meat-free wood-fired pizzas, or skip over to Continental Deli Bar & Bistro for a midday Mar-tinny or a Can-hattan over a delicious deli lunch of steak tartare and three cheese toastie.

four days in Sydney

Gin and whisky blending at Archie Rose Distilling Co.

After lunch, there are two options depending on your poison. Those who prefer and appreciate craft spirits and cocktails can go to Archie Rose Distilling Co. in Rosebery, which is currently producing gin, vodka, and white rye whisky. The cocktails at the bar are worth the trip, but for the full experience, opt for a distillery tour (A$20, includes tasting of the core range) or a gin blending class (A$95), where you’ll leave with two 200ml flasks of your own blend created with Archie Rose’s botanical distillates. Love craft beer more? Sydney’s Inner West is home to numerous craft breweries that don’t export so you can go exploring on your own or go on a crawl with Dave’s Brew Tours. The 3×3 Afternoon Tour (A$130) takes you to three different breweries – we visited Young Henrys, The Grifter Brewing Company, and Wayward Brewing Company – where you’ll get to do tastings and take a look behind the scenes.

four days in Sydney

Return to Chippendale for dinner at Ester. Trust us when we say this meal was one of the major highlights on our trip. The four-year old restaurant is well run and Chef Mat Lindsay keeps guests coming back for more with Ester’s famous king prawns (A$39) with umami fermented shrimp butter and fried capers and the lovely fermented potato bread (A$22) served with trout roe, cream cultured from kefir grains, and dashi jelly.

Day 4: Visit the Southern Highlands

Fairy Bower Falls, Morton National Park. Image courtesy of Destination NSW.

Blue Mountains, Hunter Valley, and Canberra are some of the day trips from Sydney that most international travelers would have heard of. Consider a path less travelled to the Southern Highlands instead; the region is known for its cooler weather, charming villages, a diverse landscape – and the best part? The drive south from Sydney is less than two hours.

Those into gourmet living will have a ball of a time with food experiences in the Southern Highlands. From truffle hunting in Robertson to cellar door wine tastings in Berrima, and farmers markets to cafes in quaint heritage buildings, we can’t tell you how underrated the area is for international tourism. Nature lovers are also spoilt for choice. The Corbett Gardens hosts an annual floral festival, Tulip Time, in spring – 75, 000 tulips definitely make a spectacular display. If you prefer wildlife to manicured gardens, see the pretty Fairy Bower Falls or head to Bangadilly National Park, which is great for wildlife photography and hiking.

If you can afford to spend another night or two in Australia, consider extending a day trip to the Southern Highlands with an overnight stay. There’s plenty of fresh country air and and quaint B&Bs to go around; alternatively, rent a campervan and make an adventure out of it!

This article was made possible by Destination New South Wales.

Top Image: Newtown, King Street. Image courtesy of Destination NSW.