Steps away from the surf and sand of Cronulla Beach, at the south end of Cronulla’s Esplanade, is Mediterranean-led seafood restaurant Bobby’s. Open 11am until late every day, a beach-club front room gives way to a more formal dining space out back. Executive chef Pablo Tordesillas (ex-executive chef Otto & Tottis) and head chef Shaun Baker (Pier, Yan Restaurant, Bills Restaurants) have designed a menu with a modern ocean-to-plate ethos, with small plates including a brioche prawn roll and Cantabrian anchovies on toast and larger plates spanning everything from fish and chips and barra burgers to a whole rock lobster tagliatelle. Signature cocktails include a sgroppino (lemon sorbet and prosecco) and the ‘Shire Standard’, with vodka, lychee, passionfruit liqueur and lemon. Bobby’s is proof that the Shire is all grown up, with a burgeoning dining scene set to stand on par with the inner city. 6R The Esplanade Cronulla; bobbyscronulla.com.au

Restaurant power couple Alessandro and Anna Pavoni have made big moves in Manly with multi-venue Cibaria, on the promenade inside the Manly Pacific Hotel. From the bustling restaurant to cocktail bar 55 North, it’s beachfront all-day dining, the Italian way. Designed with various ‘-ria’s’ in mind, Cibaria offers a cafeteria, gelateria and tortaria (pastries and cakes), as well as a trattoria menu spanning forneria (pizza), antipasteria (deli goodies), salumeria (cured meats), cruderia (crude), spaghetteria (pasta) and pasticceria (desserts). As with all Pavoni and Ormeggio venues, the overall dining experience draws inspiration from Italian traditions with a true sense of place – in this case, as with Ormeggio at The Spit, an oceanic experience perfect for a Sydney long lunch. 55 N Steyne, Manly; cibariamanly.au

The MCA has painted a new picture at its once-casual rooftop cafe, with fine-dining venue Canvas. Established and emerging chefs take up set residencies in what is one of Sydney’s most scenic dining rooms, the first of which was Josh Raine, executive chef at the late, great Tetsuya’s. Current chef-in-residence James Scott (Sepia, Lumi) hones his skills with local seasonal produce and native ingredients, while also nodding to his own Scottish heritage and experience cooking abroad. Open only for lunch (nights are reserved for events), the space is done in a restrained palette of neutrals and natural timber, allowing the spectacular views and exceptional food to bring the real drama. Level 4, Museum of Contemporary Art Australia, 140 George St, The Rocks; mca.com.au

Lunching at Pilu is like stepping into a Mediterranean island getaway, complete with white sands and blue skies but without the jetlag, plus there’s no battling crowds for the best table in the loveliest white-painted weatherboard cottage on Freshwater Beach. It’s casual Italian in the prettiest of settings, and it’s been a covetable lunch spot on the Sydney dining scene for decades. The sophisticated menu is inspired by owner Giovanni Pilu’s Sardinian heritage, and has been this way since the restaurant first opened in 2004. Three-hour-slow-roasted, salt-crusted free-range suckling pig is still on the menu, having secured its place among the city’s most famous dishes. Whether it’s a long lunch, a weeknight meal or a special occasion, Pilu’s effortless blend of elegance and warmth makes every visit feel like a sun-drenched Sardinian escape. Moore Rd, Freshwater; pilu.com.au

Giovanni Pilu and Marilyn Annecchini have lifted the curtain on Flaminia, a light-filled Italian dining room perched above Circular Quay – their first new opening in more than two decades. If Pilu at Freshwater is anchored in Sardinia, Flaminia widens the lens, casting its gaze across Italy’s great port cities. Cagliari, Naples, Genoa, Venice, Palermo – each leaves a subtle imprint on the menu. A crudo bar kicks things off with oysters, scallops and the day’s freshest catch, there’s antipasti made for sharing and seafood pastas to compliment the waterside location. Expect Sardinian piccolo fritto misto, paccheri allo scoglio and a and a slow-roasted suckling pig from Cagliari, a dish closely tied to Giovanni’s heritage. Dolci stay sun-soaked and traditional: crema fritta and pandolce Genovese. The drinks list keeps the coastal thread running. Wines trace Italy’s shoreline from Liguria to Sicily, with a spotlight on Sardinia’s native varieties, and the cocktails have a sense of fun – from La Via della Seta out of Venice to a Pesto Bloody Mary from Genova and a Mirto Rosso Sour from Cagliari. Pullman Quay Grand Sydney Harbour, Level 2, 61 Macquarie Street, Sydney; flaminia.com.au

Perched on the harbour with views to the bridge, you can tick off all the major harbourside landmarks over your pandan paloma and wagyu beef tartare or Moreton Bay bug spaghettini. Sails is owned by the same crew behind Ormeggio on the Spit, Ripples, Aqua and Atki, so they certainly know how to get the sparkling waterfront vibe just right. Everything is inside, but massive bifolding doors open and awnings pull back, so front row tables are open to the sky. 2 Henry Lawson Ave, McMahons Point; sailslavenderbay.com

For those of us who won’t be making it to the Mediterranean this year, there’s St Siandra. The room’s triangular shape, combined with the large glass windows, means just about every table gets a coveted window seat. On a sunny day, bring your sunglasses. The restaurant has a picture-perfect position, jutting out over the water. Depending on what the tide is doing, you could be dining right over Middle Harbour as you take in the view of the bobbing boats and cliffside houses built into the lush green hills of Clontarf. It’s not quite Amalfi, but about as close as we’re going to get without hopping on a plane. 75 Lower Parriwi Road, The Spit Mosman; stsiandra.com.au

Climbing the stairs to the Rose Bay institution before sweeping through the glass double doors, it becomes apparent why a table here has been the hottest ticket in town for more than 30 years. First opened in 1994 by Judy McMahon and her late husband, Michael McMahon, Catalina has remained true to the couple’s original vision, which was to create experiences for diners that are relaxed, luxurious and anchored by the restaurant’s extraordinary location. Menus change daily but favourites remain a staple and seafood sits at the heart of the cuisine. Lyne Park, Rose Bay; catalinarosebay.com.au

Born in Brisbane, Felons microbrewery and beer hall on Manly Wharf expanded its footprint further next door with Felons Seafood in June last year. There’s not much that can beat beer and seafood by the water during a Sydney summer, and Felons’ core range offers a refreshing selection of crisp lagers, punchy ales and lip-smacking cider and ginger beer. Both venues are slinging impressively Sydney-coded menus – overseen by ex-Rockpool chefs Corey Costelloe and Luke Bourke – which are packed with (unsurprisingly) beer-friendly beachy snacks and sustainable seafood mains. You can even hop off the ferry and tuck straight into old-school fish and chips at the newly opened takeaway kiosk Manly Fish & Chips, with optional add-ons like tallow fries, as well as burgers, chilled oysters and prawns, salads, poke bowls and more. Felons Manly; E Esplanade, Manly felonsbrewingco.com.au

Beloved UK chef and TV star Rick Stein has been a permanent fixture on our east coast dining scene for more than 15 years. With two successful NSW restaurants already to his name, Stein and his wife Sas have now opened their first Sydney restaurant, Rick Stein at Coogee Beach – a 224-seat beachfront venue on the ground floor of the new InterContinental Sydney Coogee Beach. Seafood is, of course, the star of the menu, but what makes this new venture most exciting is that there is something for everyone – whether you’re after lobster thermidor or some Sydney rock oysters and a cold beer after a day at the beach. Along with more elevated offerings, such as the spanner crab souffle, you can also expect many of Stein’s signature dishes, including his classic fish pie. 242 Arden St, Coogee; ricksteinatcoogeebeach.com.au

Brian Geraghty’s diner has long been a favourite with weekend long-lunchers. The light-filled dining room makes the most of its location, with all tables providing river views. The six-course menu benefits from a seasonal rotation of local produce, with suggested drinks pairings for each. A buttery Sigurd Hoyde chardonnay may team nicely with beautifully light kingfish, followed by succulent Murray cod with yuzu and pepper. A perfectly-sized portion of tender glazed duck may come with desert lime and kosho, paired with a Stefano Lubiana pinot noir. From the delicately crafted starters to the optional (but recommended) cheese to finish, this is picturesque destination dining at its finest. 1 Calabash Point, Berowra Waters; berowrawatersinn.com.au

With Quay’s imminent closure on Valentine’s Day, February 14, 2026, its decades-long run as one of Sydney’s premier destination diners is now drawing to a close. It’s not going to be easy to say goodbye – Quay might have been serving for over 20 years but Peter Gilmore’s flagship fine diner has never looked or felt fresher. Spotted gum tables along with custom-made leather chairs and a royal blue carpet that stretches endlessly out to sea cements this fine-dining staple in its Circular Quay locale. The showpiece remains the Sydney Opera House with its glowing white sails, which can be admired from all angles. When it comes to the eight-course tasting menu, Gilmore is still at the top of his game. If you can snag a table before last service, be sure to save room for the iconic Snow Egg. Here’s to you, Quay – you will be greatly missed. Upper Level Overseas Passenger Terminal, The Rocks; quay.com.au

Only Bennelong could make turnips sexy. In a dish of sashimi scallops, it lends a delicate crunch to an otherwise silky smooth oyster cream dressing. Later, we find it playing a supporting role in a magical dish of lightly seared coral trout, flown in from the Great Barrier Reef, served with shavings of southern squid on a koji emulsion bed. Granted, turnips aren’t the only star of the show. There’s also that knockout location inside the Sydney Opera House. But back to the menu. Tasmanian octopus served with peanuts, sesame aioli and a heavenly warming ssamjang successfully takes top billing on a stellar three-course menu that reads like an all-star cast of the flavours of modern Australia. The now-iconic pavlova, complete with meringue shards replicating the Opera House sails, is a sure-fire way to end the performance on a high note. Sydney Opera House, Sydney; bennelong.com.au

Alessandro Pavoni and Victor Moya’s institution is infused with the soul of Southern Italy. The dining room with its white stucco walls, rattan furniture and well-loved Turkish rugs resembles a luxe beach house, overlooking yachts bobbing in d’Albora Marina. A meat-free menu inspired by the Puglia region revolves around sustainable seafood – MSC-certified swordfish cooked over charcoal and plated with zucchini and basil cream is as satisfying as any steak; grilled Aquna murray cod sings with tomato pil-pil and black olives. The wine list is an encyclopaedia of Italian varietals; a bottle of DOCG sparkling Franciacorta ideal for the feast to come. The signature delizia al limone is a theatrical finale – the meringue topping seared by a blowtorch tableside, then finished with a zest of lemon that fills the room with the scent of citrus. It’s the Amalfi coast, by way of Mosman. D’Albora Marinas, Spit Rd, Mosman; ormeggio.com.au

How is it that a Sydney restaurant can last for 30 years and somehow remain relevant? In the case of Sean Moran’s beachside gem, it’s a steady commitment to honest cooking that lets peak-season, farm-fresh produce do the talking. Here home-style meets modern, with the line-up changing daily depending on what’s available from Moran’s own farm at Bilpin and other ethically-sound suppliers. There’s a coastal daydream of a dining room where time-honoured benchmarks like chubby honey prawns, endlessly tender roast chicken and wobbly baked custard continue to shine. Weather permitting, there’s also a chance to dine al fresco to make the most of dazzling ocean views. 270 Campbell Parade, North Bondi; seansbondi.com.au