Sydney’s restaurant and bar culture is as rich and historic as the city itself. From the cobblestoned lanes of The Rocks to a vintage paddlewheeler cruising across the harbour, Sydney’s iconic restaurants and bars offer plenty of ways to raise a glass to its past. Whether you’re a history buff or just love a good pint in an old British setting, these iconic drinking places embody the spirit of old Sydney.
The Lord Nelson: Pouring Since 1841
The Lord Nelson is the only hotel in Sydney to have held its license since 1841, making it the city's longest-licensed hotel. An old photograph from 1852 helped restore the building to its original glory during renovations in 1986. Its old sandstone brick walls, creaky floorboards and classic fireplaces have stood the test of time, preserving its 19th-century charm.
The pub brews its own award-winning ales and craft beers onsite, paired perfectly with hearty classics like a Ploughman’s lunch. You can even stay the night in cosy accommodation that reflects the same old-world charm as the bar downstairs. Loved by locals and foreigners alike, this heritage gem remains one of the city’s most beloved pubs.
Sydney Showboats: A Legendary Experience On The Harbour
If you want to experience a legend of Sydney Harbour, the Showboat dinner cruise in Sydney is a must-try. Operating since 1987 and inspired by 19th-century American paddlewheelers, it is Sydney’s longest-running cabaret dinner cruise with a well-stocked bar onboard.
To complete the experience, the cruise also serves a freshly prepared three-course meal, paired with the spectacular, hour-long live cabaret performance ‘Voyage of Love’. As the Showboat cruises down the harbour, you’ll see Sydney’s most famous landmarks, including the Sydney Opera House, the Harbour Bridge and the glittering city skyline. An all-in-one experience that outshines all the historic old pubs you've heard about!
The Hero Of Waterloo: Sydney's Secret Tunnel Pub
Built in the old colonial regency style with ashlar stone, The Hero of Waterloo is one of Sydney’s oldest pubs. It’s famous for the legend of a secret tunnel that once led from the cellar to the harbour, used for rum smuggling and trapping drunken sailors into forced labour.
The cellars still have shackles on the walls and the tunnel entrance can still be seen today. Classified by the Heritage Council and the National Trust, this pub remains one of Sydney’s most talked-about historic landmarks. And guess what, you can grab a drink in this haunted piece of Sydney history.
The Australian Hotel: A True Blue Pub In The Rocks
The Australian Heritage Hotel is one of the oldest pubs in The Rocks. It’s been serving Sydney since the early 1900s and remains a proud supporter of Aussie-made beer.
Inside, you’ll find warm timber walls, vintage charm and an all-Australian drinks list that celebrates local brewers. The menu keeps things classic with pub favourites like schnitzels, burgers and the famous Aussie-themed pizzas. With a rooftop bar overlooking the city skyline, this heritage spot is perfect for a relaxed lunch, a cold pint or live music on the weekend.
The Fortune Of War: Built by Convicts, Loved By Sailors
Built in 1828 by former British convict Samuel Terry, The Fortune of War is Sydney’s oldest standing pub building. Over the years, it became a favourite spot for sailors and soldiers — famously known as the “first and last stop ashore” for those heading to or returning from service.
Stepping inside feels like walking through time. The cosy front bar is filled with old photos, historic memorabilia and the buzz of friendly chatter. The Fortune of War is still a local favourite today, known for its laid-back atmosphere, live music and great beer selection. It’s a place where history lingers in every brick and every pint feels like a toast to Sydney’s maritime past.
Marble Bar: A Victorian Time Capsule
Marble Bar, located beneath the Hilton Sydney, is one of the city's most stunning historic venues. Built in 1893, it was designed to impress with its grand marble archways, stained glass ceilings and rich mahogany detailing, all of which have been lovingly preserved for over a century.
Today, the bar continues to embody that Victorian architecture, offering an escape from the bustle of the city above. Guests can enjoy classic cocktails or fine wines while listening to live jazz, all in an ambience that feels both luxurious and timeless. Marble Bar is not just a bar, it is a step back into Sydney's Victorian golden age.
Sydney’s heritage isn't just found in museums — it’s alive in its pubs, bars and on the harbour. Step inside, raise a glass and immerse yourself in the rich history of old Sydney!
Author Bio – Amanda Clark
A Sydney-based travel writer who loves chasing experiences that defy expectations – especially when great food and entertainment are part of the mix. From unforgettable hits to unexpected flops, I share real stories to keep the adventure honest and fun for everyone!
