Sparkling waters meet an urban community of skyscrapers, alleyways and serpentine streets in Australia’s most recognisable city. From the mellow chords of Restaurant Hubert’s live jazz filling moon-washed streets, to the curves of the Harbour Bridge casting shadows over private harbour cruises, the city hums with life at all hours, tempting travellers with myriads of epicurean delicacies, cultural experiences and once-in-a-lifetime journeys.

We’ve put together an insider’s neighbourhood guide for those keen to explore the best the city has to offer, providing a deep dive into some of our favourite places to wine, dine and explore.

Bondi/Eastern Suburbs

The white-sand curve of Bondi Beach in Sydney’s east is a staple in many visitors’ itineraries. Perfect waves draw surfers from near and far, while hardy locals take a dip in the nearby Icebergs ocean pool. Cafes and eateries press into the surrounding streets, primed for health-conscious patrons while bars and pubs lie in wait for the warm hands of sun-soaked beachgoers to cool down with a pint of local beer. A photogenic clifftop hike wraps the coast from Bondi to Coogee, offering the perfect warm up to an iced latte.

Things to do:

Surf in Bondi

With a reliable swell and famous surf culture, it would be amiss to not mention Bondi as one of the best places in the world to surf. From beginners to seasoned pros, Bondi offers some great breaks alongside its postcard-worthy curve of golden sand and vibrant atmosphere. A private lesson gives you all the attention you might need to easily tick off this bucket-list experience.

Where to Wine and Dine:

Icebergs Dining Room

A staple often captured from the sloping banks leading down to Bondi, this modern Italian restaurant boasting 180-degree views of the famous beach is synonymous with celebrations and summer. Cosy up with a glass of their sgroppino – lemon sorbet mixed with vodka and prosecco – at one of their window-side tables or sit out on the deck to soak in the sun. Perfect for watching surfers catch their next wave and that quintessential Icebergs photo to write home about. With a distinct Australian influence within their menu, indulge in green ants and wax leaf to sharpen fresh coral trout crudo – the perfect respite after a day on the sand.

Bills Bondi

Full tables covered with plates of scrambled eggs and steaming flapjacks are what is to be expected come brunch time at Bills. Made famous for their fluffy ricotta hotcakes slathered in honeycomb butter and topped with sliced banana and a dusting of icing sugar, the trendy location is cherished by locals and visitors alike and an absolute must-visit on your brunching repertoire. Although also open for dinner, we recommend sitting at one of the outdoor tables spilling onto Hall Street come brunch time and watching the parade of hungry Sydneysiders trying their luck in the infamous Bills Bondi queue.

Sean’s

Running for more than 20 years, this eccentric waterfront dining room is one of the most quintessentially Sydney dining experiences there is. Sit window-side in their eclectic, shell-lined dining room to watch the waves break over Bondi as you pull apart warm house-made bread and lick softened butter off grateful fingers. Here, Sean’s nails the basics in a daily-changing menu responsive to what is the most in-season. Whether it is the ripe crispness of heirloom tomatoes sitting alongside a mint and watermelon salad in the summer, or the comforting-crisp communion of a roast chicken main in the winter, Sean’s does simple, and does it well.

Where to stay: 

QT Bondi

With so much in the neighbouring blocks, you can take it easy at this quirky escape on High Street. Surfers and style-seekers will be your neighbours, with deluxe king rooms providing you with a balcony to watch the world go by after a day’s exploration – the perfect spot for a little room service and a glass of sparkling. A place to wash away the day with coastal calm and a little rejuvenating relaxation before ever more sun-kissed play.

Spicers Pott’s Point

Quietly tucked away on a leafy Sydney street is this former historic townhouse turned boutique hotel. Spicers Potts Point is refined and understated Sydney style at its best. Featuring just 16 rooms and four sumptuous suites, this hotel is intimate and exclusive. A rich tapestry of neutral tones, simple yet sophisticated furniture, original historic features, and art providing pops of colour throughout combine to create a tranquil and chic city hotel. Effortlessly blending historic charm and contemporary design, Spicers Potts Point is the hotel of choice for lovers of style and quiet elegance.

Inner City  

A mind-boggling maze of labyrinthine laneways coveting a spectacular dining scene and unique experiences, best explored alongside some of the top private guides in the country. In Sydney, heritage sandstone buildings stand against twisting steel skyscrapers, roads dip and turn to reveal secret bars and hidden delights, its precincts home to some of the largest global and Australian businesses representing all sectors primed for your discovery.

Things to do:

Paspaley

Paspaley Pearls represents the pinnacle of luxury and craftsmanship, offering some of the most exquisite South Sea pearls in the world. Each piece is a testament to the brand’s dedication to quality and timeless beauty. Alongside The Tailor, jewellery enthusiasts are given the opportunity to go behind-the-scenes at the Paspaley Showroom and get an insider’s look alongside a pearling expert in this tour offered exclusively through The Tailor.

Splendour

Splendour Tailored Tours offer extraordinary, tailored experiences of Sydney and other regions in New South Wales, crafted with personal interests in mind and led by an innovative local guide. Walk through doors only opened by The Tailor and Splendour, where you can experience the best of Sydney’s gourmet dining scene. Journeying from the historic laneways shadowed by the Harbour Bridge and the famous pubs that are located here, enjoying visual delicacies to accompany the produce, on to Manta Restaurant for some Sydney Harbour glamour, and then to Potts Point to visit one of Sydney’s hottest restaurants. With a local’s insight, the maze of Sydney’s streets becomes a buffet of delights served to you course by course.

Art Gallery of NSW (Sydney Modern Wing)

The Art Gallery of NSW, a cultural landmark in the heart of Sydney, has been a beacon of artistic excellence since its establishment in 1871. Housing an impressive collection of Australian, European, and Asian art, the gallery offers a rich tapestry of visual history and cultural dialogue. The newly inaugurated Sydney Modern Wing elevates this experience, presenting a stunning showcase of contemporary art. This dynamic space, with its innovative architecture and breathtaking exhibits, immerses visitors in cutting-edge installations and a diverse collection that highlights the vibrant pulse of modern artistic expression. With The Tailor, go on a private after-hours tour for a unique look into this stunning space.

Botanic Gardens

The Royal Botanic Garden Sydney, established in 1816, is a verdant oasis nestled in the heart of the city. Spanning 30 hectares, this historic garden offers a tranquil escape with its diverse collection of plants, stunning landscapes, and sweeping views of Sydney Harbour. A favourite for viewing the sparkling waters come New Year’s celebrations or the iconic Vivid Sydney light show, you can explore themed gardens, meander along picturesque pathways, and discover rare and exotic flora whilst snapping photos of some of Sydney’s famous landmarks.

Where to Wine and Dine:

Restaurant Hubert

Perhaps the most thoroughly recognised venue in Sydney, Hubert’s collection of red velvet, chestnut timber and polished brass resonates with the sound of jazz as a slice of Parisian glamour. Butter and salt take centre stage with hearty dishes and a spectacular wine list – the best residing in pages 10-51. Uncork a bottle of the minerally Pierre-Yves Colin Morey aligoté to complement the live jazz band gracing the floor as you make your way through a dinner likened to the magic of music itself. The steak bavette entices a delightful symphony, building with a velvety soft wagyu tartare and raising to a spectacular crescendo finale with the not-to-be-missed creme custard.

Mishy’s

A vibrant and eclectic restaurant that offers a unique culinary experience in the heart of the city. Sustainable produce and the freshest ingredients combine into healthy meals perfect for something lighter after days spent in opulent dining rooms.  Known for its creative fusion cuisine, Mishy’s head chef has used her globetrotting experience to inspire a menu highlighting innovative and delightful dishes.

Where to stay:

Capella

Situated in the heart of Sydney’s vibrant downtown and occupying a whole city block in the financial district, Capella Sydney will leave you breathless from the first moment you set foot in the foyer. Beneath an elegant art installation made to mimic the opening and closing of giant flower blossoms, staff greet you as if you’ve just returned home. Forget the other 192 intricately designed rooms (though they are rather lovely) and stay in one of their prestige suites on the upper floor for expansive glass windows commanding the cityscape and, for some, glimpses of the water and the Sydney Harbour Bridge. Standalone tubs complete the room’s illustrious feel alongside an in-house restaurant spearheaded by local heroes who have birthed some of the city’s most acclaimed restaurants. The Queensland coral trout and meaty scallops from Tasmania are especially divine.

Park Hyatt

With unrivalled Opera House views, the Park Hyatt Sydney is the place to be for those after unviralled views. Situated adjacent to the Sydney Harbour Bridge and overlooking the iconic Opera House, it occupies a prime location in the heart of Circular Quay and the historic Rocks district. Following a comprehensive renovation—the most extensive in 20+ years—this distinguished five-star hotel has redefined modern luxury. We recommend staying in their Cove, Harbour or Sydney Suite for spectacular views over the icons, with floor-to-ceiling windows that open onto private balconies perfect for indulging in some 24-hour room service as you soak in the sounds of Sydney.

Northern Beaches

Sydney’s Northern Beaches offer a stunning blend of natural beauty and coastal elegance, stretching from Manly to Palm Beach. This idyllic region is renowned for its pristine sandy shores, crystal-clear waters, and relaxed atmosphere. Whether you’re surfing the iconic waves at Manly, dining at waterfront restaurants, or exploring the scenic trails of Ku-ring-gai Chase National Park, the Northern Beaches provide a perfect escape for those seeking both adventure and tranquillity.

Things to do:

Local Eyes (harbour and northern beaches)

Introducing Jamie and Alex: long-time friends of The Tailor and proprietors of Local Eyes, a private charter and guiding business supplying a beautiful collection of unique and interactive day tours around iconic Sydney and the greater New South Wales’ area. Able to tailor tours to your liking, you can spend a leisurely day exploring Sydney’s beautiful northern beaches and immerse yourself in the local surf culture. Walk along the picturesque Palm Beach and the sheltered waterways of Pittwater and Broken Bay, find the secret nooks and places close to your hosts’ hearts and be invited into their home to meet their enthusiastic golden retriever. Indulge in some authentic Australian hospitality on the waterfront and be guided by their local insight into Sydney.

Sea Planes to Cottage point

Situated deep in Ku-ring-gai Chase National Park on the tip of Sydney’s Northern Beaches, Cottage Point Inn is one of Australia’s most exclusive dining experiences. This elegant waterfront eatery has created one of Sydney’s most dazzling menus, with fresh local produce taking centre-stage. Arriving at the restaurant via private seaplane with amazing views of Sydney Harbour and the northern beaches as your appetiser, this former general store and post office offers a European-meets-Australian-style dishes in one of Sydney’s most stunning dining spots.

The Harbour

Often hailed as one of the most beautiful natural harbours in the world, Sydney’s Harbour is the dazzling crown jewel of the city. Its sparkling waters are framed by iconic landmarks such as the Sydney Opera House and the Sydney Harbour Bridge, creating a breathtaking panorama. Visitors can enjoy a range of experiences, from sailing and cruising to dining at waterfront restaurants and exploring the historic precincts along the shoreline.

Things to do:

Opera House (BTS)

The Sydney Opera House, an architectural marvel and UNESCO World Heritage site, has graced the shores of Sydney Harbour since its completion in 1973. Designed by Danish architect Jørn Utzon, its iconic sail-like structures symbolize Sydney’s innovative spirit and cultural vitality. Go behind the scenes at this Australian staple alongside your private guide and uncover the rarely seen aspects that make this building such an Australian marvel.

Taonga Zoo

Perched on the scenic shores of Sydney Harbour, Taronga Zoo has been a beloved destination since its opening more than 100 years ago. Stay overnight at one of their new eco-retreats and wake up to animals grazing right outside your window or go behind-the-scenes and experience what it’s like to be a zookeeper for a day. See the giraffes and capture a photo with the skyline of Sydney framing that perfect shot.

Bridgeclimb

BridgeClimb Sydney offers an exhilarating adventure and a bucket-list Sydney experience, inviting you to conquer the iconic Sydney Harbour Bridge. Since 1998, thrill-seekers and sightseers alike have ascended this world-famous structure, enjoying unparalleled 360-degree views of the city and its sparkling harbour. Led by expert guides, embark on a journey that combines heart-pounding excitement with fascinating insights into the bridge’s history and engineering. The best time for this climb is their nighttime climb during the city’s famed VIVID Festival, although, a twilight climb to capture the technicolour sunsets are just as divine.

Where to Wine and Dine:

Bennelong

The soaring arches and dramatic curves of Bennelong restaurant – housed in the concrete belly of a Sydney Opera House sail – oozes an elegant and sophisticated charm. Designed to impress, the hushed dining lighting paired with leather chairs alongside a floor-to-ceiling harbour view make this an unmissable dining location for epicurean (and architectural) enthusiasts. Take a seat beside the sun-soaked windows and indulge in the brown butter and lemon emulsion of their Moreton Bay bug, or the textural harmony that is their confit duck leg. It is the perfect place to indulge in some quintessential Australian cuisine, finishing with a classic pavlova; meringue peaks mimicking the sails of your dining destination.

La Foote

Le Foote is an historic, heritage listed venue in The Rocks. Part Parisian wine bar, part Mediterranean grill, it pours a jovial atmosphere, expert service, and some of Europe’s finest wines. Art and romance waltz within its walls. Classical Jazz, Euro-tech groove, and the promise of delicacies cooked over charcoal wind through its labyrinthine rooms, crooks and crannies aplenty for an intimate meal of fresh taramasalata and crudites followed by swordfish rib eye and Black Angus striploin.

Clam bar

Inspired by the great steakhouses of New York, Clam Bar begins your culinary journey with a full raw seafood bar that leans opulent. Oysters Rockefeller, caviar and sparkling prawn cocktails beckoning from the menu, alongside glasses of dry sparkling Burgandy to tempt you into a long lunch. Take a seat beside one of their decorated windows facing the street and people-watch over forkfuls of their spaghetti and clams; the al dente strands lathered in a luscious umami-rich butter and garlic sauce. Finish with a rib-eye steak cooked to perfection, dripping with anchovy butter.

Where to stay:

Crown Towers Sydney

Sydney’s first six-star hotel effortlessly combines the best traits of a chic city hotel and prestigious villas. Here, you can enjoy the hotel’s day spa, luxury shopping, outdoor pool and tennis court, without a need to leave the hotel premises, should you so choose. Sprawling views across the city and Sydney Harbour can be found on the upper floors, where we recommend you reside. Specifically, the grandeur of the Premier Suite or Executive Harbour Bridge Suite will be tough to beat, with floor-to-ceiling windows letting in that famed Australian sunshine, king beds and lavish amenities. Fourteen dining venues await your palette, with Nobu the most notable. Try a bite of their Nobu tacos and yellowtail jalapeño dish as you soak in the view of the harbour.

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