5-day itinerary to see the very best of Sydney in style

Morning 

Start your trip by ticking off some of Sydney’s most famous icons. Book a dawn climb on the Sydney Harbour Bridge to see the sun rising over the harbour with BridgeClimb, or paddle beneath the famous archway and over to the Sydney Opera House on a Sydney Harbour Kayaks tour.

If you prefer a more relaxed wander, join a mindful walk around Circular Quay and the Royal Botanic Garden Sydney with the Hike and High Tea at Level 36 tour guided by Soulful Hikes. Running every Saturday, the two-hour walk ends with a special high tea at Altitude at the Shangri-La Sydney, where the harbour views are just as spectacular as the pastries. 

BridgeClimb Sydney, Sydney Harbour

Afternoon  

For lunch, taste the city’s most delicious icons. Slurp Sydney rock oysters at Opera Bar by the Sydney Opera House or dine on local NSW ingredients at Cafe Sydney; you’ll have prime views of the harbour at both as you dine. Catch the tram down George Street to find some of Australia's best shops and boutique designers, as well as social media-famous sweets: try TikTok’s favourite French hot chocolate at Manon Brasserie in the QVB or visit Black Star Pastry's city outpost for a slice of their Strawberry Watermelon Cake, said to be the most Instagrammed cake in the world!

If you prefer to tick off all your foodie must-trys in one go, The Taste of Sydney tour with Ultimately Sydney runs every Saturday and is a five-hour, four-course travelling lunch that tastes some of the city’s best dishes. 

Opera Bar, Circular Quay

Evening 

Head to one of Sydney's city theatres to check out a memorable performance, such as the Sydney Opera House, State Theatre, Sydney Theatre Company or Capitol Theatre. Check our guide to what musicals are currently showing here and what theatre shows are currently showing here. End your iconic night out with drinks at the highest bar in Sydney, Bar 83. This revolving bar within Sydney Tower serves spectacular cocktails alongside the prettiest views of the city’s twinkling lights.  

Bar 83, Sydney City - Credit: Robert Walsh

Morning 

The leafy suburbs of the inner east are home to some of the hottest bars and restaurants in the city, as well as some of Sydney’s most stylish residents. Start off your journey with the Sydneysider's favourite meal of the day: brunch. One of the most popular places for a long and lazy breakfast is Bills in Surry Hills. Its founder, celebrity chef Bill Granger, is credited as the inventor of Australia’s most infamous brunch item, avocado and toast. There are plenty more cafe options along Crown Street and surrounds – such as Paramount Coffee Project, Artificer and Cafe Kentaro. Or head to its northern end to explore Darlinghurst and Oxford Street; Mayflower is one of the prettiest brunch spots, a collaboration of food, art and floristry. 

Avocado on toast at Bills Surry Hills - Credit: Anson Smart

Afternoon  

Enjoy a spot of shopping in the area – including Vampt Vintage for collectable homewares, Zoo Vintage Emporium for funky fashions and carefully-curated books at Oscar & Friends, as well as the high-end fashion boutiques of the neighbouring suburb of Paddington. Alternatively, uncover the treasure-trove of wonderful art galleries in the area, including Brett Whiteley Studio, M2 Gallery and the Sherman Contemporary Art Foundation.

Break up the day with a long lunch on one of the many rooftop bars in Sydney – The Butler in Potts Point, the Light Brigade in Woollahra or Slims in Darlinghurst are all popular bar-hopping spots with amazing views. 

The Butler, Potts Point

Evening 

Theatre lovers should check out what’s on at Belvoir St Theatre in Surry Hills, where its programming takes pride in Australian filmmakers and Indigenous stories. Wine connoisseurs can book a tasting at Urban Winery at Moore Park, Australia’s first fully functioning city-based winery. If you’re looking for a local’s guide to the best restaurants in the neighbourhood, join a three- or four-course dining tour with The Sydney Connection.  

Urban Winery Sydney - Credit: Urban Winery Pty Ltd

Morning 

Sydney’s inner west is a vibrant community of unique suburbs with treasures hidden in every alley, street and warehouse. Marrickville is famous for its diverse and delicious cafes: try Valentina’s for comforting American all-day diner food or Kurumac for a Japanese-inspired breakfast. After fuelling up for the day, discover some of the suburb's funky street art along Faversham Lane, Chalder Street, Marrickville Road and Illawarra Road.

Cod roe toastie at Kurumac, Marrickville

Afternoon  

The inner west is famous for being Sydney’s craft beer hub and you can hop from brewery to brewery to sip on some of the best locally made pints. Marrickville is home to the likes of Bob Hawke Beer & Leisure Centre, Philter and the naturally fermented brews at Wildflower. In Newtown, visit Young Henry’s, Willie the Boatman and Wayward Brewing. Most breweries can also serve you up a feed with your brews. If you’d like a designated driver to guide you through this hoppy journey, book into a brewery tour with Dave’s Tours, which stops in at three of Sydney’s best. 

The Bob Hawke Beer & Leisure Centre - Credit: Jessie Ann Harris

Evening 

Spend the afternoon wandering up and down King Street and Enmore Road in Newtown, where vintage boutiques, design shops and plenty of bars and restaurants create a colourful vibe from day to night. Book in for entertainment of a different kind at The Imperial Hotel in Erskineville. Famous for its starring role in The Adventures of Priscilla, Queen of the Desert, this camp icon is one of the best places to celebrate LGBTQIA+ culture with Drag N Dine, music and cabaret performances. If your perfect night is less about dance floors and more about dessert, cap off your evening with a scoop of award-winning ice cream from Cow and the Moon – their almond affogato flavour was voted world’s best gelato in 2014. 

Cow and the Moon

Morning 

Sparkling blue ocean, fun eateries and a laid-back beach lifestyle sums up Sydney’s world-famous Bondi. Brave the winter waves for a morning surf lesson with Lets Go Surfing – there are lessons for beginners and more advanced wave riders. After your time in the water, warm up with a coffee and cooked brunch from one of Bondi’s best cafes – Porch and Parlour serve delicious nourishing meals alongside live music and their own ceramics shop.  

Surfing at Bondi Beach

Afternoon  

Winter is whale-watching season in Sydney, and a coastal walk offers the best vantage point for spotting some of the 40,000 humpback and southern right whales that make their way along Sydney’s coastline in their annual migration from Antarctica. Head south on the two-hour Bondi to Coogee Coastal Walk, where the clifftop track offers incredible views of the crystalline coves of Bronte, Tamarama and Gordons Bay. From Bondi you can also head north and take on part of the epic 80km Bondi to Manly Walk. The section between Dover Heights and Watsons Bay offers panoramic views out to the ocean, and North Head in Manly is known for being whale-watching territory (take the ferry from Circular Quay to speed up your walk!). If you aren't visiting in winter, the views are just as enchanting minus the wildlife.

Mother and calf whales spotted along the Sydney coastline, Bondi Beach

Evening 

If you’ve ended up across the bridge in Manly, continue your coastal exploration aboard a magnificent 61-foot yacht for a sunset sailing cruise with Manly Sailing. If you’ve made it to Coogee, do as the locals do and book in for a feed at the Coogee Pavilion, home of three levels of dining, drinking and dancing. 

Coogee Pavilion, Sydney East

Morning 

Fuel up for your last day in Sydney with a weekend tradition: morning yum cha. Find a table at one of the famed institutions in Haymarket like The Eight, Emperor's Garden or Palace Chinese. Don’t leave without getting a mango pancake from the trolley – a Sydney-invented dim sum dish. Another Saturday-morning custom, and a great way to try local produce from all over NSW, is heading to one of the city’s weekend markets. Carriageworks Farmers Market is held just near Redfern Station and here stallholders from across the state sell their cheese, cured meats, vegetables, flowers and more.  

Yum cha options at The Eight, Haymarket - Credit: Natarsha Brown

Afternoon  

If you want to continue grazing, Sydney’s Chinatown offers streets and alleyways full of delicious treats from across Asia. Find Taiwanese snacks at Mother Chu's, steaming-hot xiao long bao (soup dumplings) at Nanjing Dumpling or flaky roti from Malaysian favourite Mamak. Learn more about the history of Chinatown and Chinese migration in Sydney (and taste some favourite dishes along the way) on a tour with Local Sauce Tours. 

Get into high spirits at a workshop at some of the city’s best craft distilleries. Archie Rose make one of Sydney’s most loved gins – join a workshop at their Rosebery distillery and blend your favourite botanicals into your own mini bottles. Rum haven Brix Distillers in Surry Hills offers cocktail making classes and rum spicing workshops or simply explore the distillery on a behind-the-scenes tour. 

Archie Rose Distilling Co., Rosebery

Evening 

Tonight, head for dinner at Burwood Chinatown. This neon-lit food precinct has become a popular spot for late-night snacking, with traditional restaurants and more than 30 street food stalls hawking everything from guo kui (clay oven-baked flat breads), lamb skewers, sweet egg waffles, bubble teas and more. 

Burwood Chinatown, Burwood