A guide to Mosman

There’s not many “best of” lists that Ormeggio at the Spit hasn’t graced during its 11 years at the D’Alboro Marina in Middle Harbour. The Italian fine diner is one of the city’s top long lunch spots, it has the kind of waterfront views residents pay tens of millions to enjoy, and until recently, adhered to the rules of fine dining bred from Michelin-starred training. Now, after ten years of silver service at Ormeggio, Alessandro Pavoni decided to change the game, still channelling the spirit of fine dining, but in a more relaxed, casual tone.

Probably one of the best beaches the North Shore has to offer, Balmoral Beach has it all - rock pools, a boardwalk, netted swimming baths, a playground, picnic tables, restaurants, the best hot chips you've ever eaten, a rotunda (more often than not hosting a beachside wedding ceremony) and even an adjacent skate park.

Chowder Bay is on the southern side of Sydney's Middle Head Peninsula where a steep bushy backdrop is countered by a gorgeous harbour side frontage. The area hosts historical buildings and remnants of past military occupation; only reopened to the public in 2007, Chowder Bay - whose name grew from the whalers who made chowder from the bay's abundance of seafood - is a very charming spot.

There are few places in Sydney that can match the Barracks for pomp and jaw-dropping views. We’re not talking a little corridor of harbour. The Gunners’ Barracks has a 180 degree, uninterrupted, waterfront panorama that stretches from the CBD all the way round to North Head, so be sure to request a spot on the big verandah to take full advantage of it.

Head into the d’Albora Marina, past the display model speed boats worth $50,000 a pop and out towards the water. On your right is the refined, Italian fine diner, Ormeggio at the Spit, with Alessandro Pavoni at the helm and well-tailored maître Ds at the door. To your left, however, is a little 50-seat, open-air restaurant staffed by smiling young wait staff in white tees and striped aprons, where punters can turn up barefoot and even BYO with a hint of a sneer. 

They guys behind the Greens and Acre Eatery have brought their green thumbs and cocktail shaking hands to a Mosman rooftop. The Fenery has views out over the harbour all the way to North Head and they've brought urban farmer Adrian Baiada on board to build them an outdoor kitchen garden. Inside the kitchen they've installed a josper, a wood-burning grill, and out on the garden terrace there will be a dedicated rosé bar, plus a gin room showcasing bottles from local distilleries.

There’s nowhere to hide at Public Dining Room. The restaurant, built on the old Watermark site, is a huge, open-plan space hugging Balmoral Beach with nothing but a window separating you from the dog walkers, beachgoers and fishermen occupying the waterfront. But this is part of its charm. You can soak up the last of the sun as you take a post-prandial stroll down the pier where locals bob for squid and boats rock with the swell.

The Buena is best described as a very fancy pub. Careful attention – not to mention serious cash – has been paid to the high-end detailing, with the timber panelling, feature windows and gold trimmings echoing the luxurious mansions for which the suburb is famous. Downstairs, the Buena Bar has a central island bar surrounded by dark timber and plush suede booths. Head upstairs and you’ll find the Vista Bar, an impressive, light-filled space with exposed beams and potted botany.

Like the cute button-patterned teapot they've put your orange pekoe in? You can go into the store and buy one just like it when you're done – Burnt Orange is that kind of place. It's also the kind of place where you can sit on a grand old wooden balcony and cast your eyes over Middle Harbour or the kookaburras picking at the lawn down below – both café and shop are housed in an old golf club built back in the '20s that was pretty much made for afternoon tea. Kick yours off with a glass of very cold Redbank Emily brut and prepare for a cake-and-tart onslaught.

Whole days could be whiled away in this pleasant beachside fantasy made real by so many blue-and-white stripes and so much walnut detailing. Hit the bistro for breakfast and the hum of the coffee machine plays backdrop to fluffy omelettes generously stuffed with ricotta and to crisp, golden French toast. For locals recovering from one too many Espresso Martinis, a bowl of greasy fried rice prefaced with a Bloody Mary – tall, not soupy – is the right kind of tonic.

Obelisk Beach is one of Sydney's few legal nude beaches, so if you're feeling the natural vibe, then get to strippin'! You'll need to park up the hill and walk a fair way to get here – it's at the bottom of a long series of steps, and as far as beaches go, she's a small one. But it's worth it for the gorgeous views of Camp Cove and Parsley, Watsons and Vaucluse Bays in the distance. 

At this shabby-chic café you'll find outdoor tables with comfortable banquettes for people-watching with a relaxed and unpretentious vibe. Service is prompt and efficient, the café buzzing and so are the waitstaff who attend to everybody in a timely fashion. Caffeine addicts north of the bridge will be happy to know that the coffee here is kick-ass. The menu is succinct, with lots of killer and very little filler to be found, moving from inventive salads to heartier fare; the corn fritters with house-cured ocean trout topped with avocado salsa and a poached egg are a must.

Street Bean Espresso is a hole-in-the-wall café set in the sunny pedestrian mall at the fork of Military and Spit Road. There’s not much to this it – the place is so small they can only fit two blades on their ceiling fan – just four courtyard tables and a tiny indoor nook if it’s cold out. It may be a small operation, but the coffee is good, the waffles are hot and the service is friendly. We're backing the little guy this time.

This Moroccan/Sri Lankan/Jamaican mash-up (yes, really) is popular with locals that swing by for a meat fix after an early screening at the Hayden Orpheum Picture Palace across the street. The food menu runs the gamut from super addictive "afro" potato fries to five-hour spicy lamb shanks, and each dish comes with an exotic anecdote whether you want it or not. They have a reasonable cocktail list, a lengthy tequila list, and a budget-friendly wine list. Ask for the bin ends version if you're after a rare gem.

For respite from the relentless traffic of Military Road pop into the Hotel Mosman for some of the cheapest steaks north of the bridge, plus they keep the kitchen open until midnight for all you hungry night owls. Upstairs the garden terrace looks out over the grounds of Boronia House and is an ideal location for an alfresco Sunday lunch. Hotel Mosman (or “the duck” as it is sometimes affectionately called) also host functions that include staff, canapés and free room hire.

It's beautifully laid out, the paths are wide and meandering, its views of the city are legendary, and – most importantly – the place is full of animals. Really interesting ones too: along with the lions and tigers and bears (oh my!) there are impossibly cute baby elephants, chimps and giraffes, as well as Taronga classics (pygmy hippos, the komodo dragon, koalas, platypi, Andean condors) and many exotic creatures you may not be immediately familiar with. We don't want to play favourites, but if Malaysia's noble bear-cat is binturong, we don't want to be binturight.

In 2019, Taronga took bold strides into the luxury accommodation market with its purpose-built 62-room Retreat. This complex of sleek, timber-clad lodges encircling a private bushland garden is a remarkably successful fusion of elegant sophistication and sustainable design, where wildlife and the high-life exist side by side.

This popular overnight glamping experience starts after the gates have closed on daytime visitors and continues until they open again at 9.30 the following morning. The staff looking after and escorting the group of campers are knowledgeable, bubbly and approachable. They pack in as much as they can before the 11pm ‘lights out’ – you'll meet critters at sunset; see lions, tigers, snow leopards and a sun bear fed late-night snacks; and dine at the zoo’s restaurant.