Explore Eastside Sydney

Explore Eastside Sydney sightseeing – Things to do in Sydney

If you’re visiting Sydney for the first time, you’re sure to make a bee-line for the sparkling harbour, followed shortly after by iconic Bondi Beach. However, for a truly authentic Sydney experience, be like a local and discover Eastside Sydney. It is nestled between the two and a mere stone’s throw up the hill from the CBD. Off The Beaten Track, why not explore Eastside Sydney sightseeing?

Key suburbs

This area consists of the neighborhoods of Darlinghurst, Potts Point, Kings Cross, Surry Hills, and Woolloomooloo. The eclectic Eastside stacks up against other international areas that bear a similar compass point, such as East London and East Village NYC. They are stylish while being gritty and arty, and packed with entertainment venues. Off The Beaten Track, why not explore Eastside Sydney sightseeing?

Killer Bars and Restaurants Off The Beaten Track Explore Eastside Sydney sightseeing

Visit and experience killer bars and restaurants, vintage and new street fashion, co-working spaces for the digital nomad, and above all, where local creatives love to hang out.

Do Darlo

What is on offer in Darlinghurst?

Darlinghurst, or Darlo as the locals affectionately call it, is home to the world’s largest Mardi Gras Festival in March and is also an enclave for cool restaurants, rooftop bars, music venues, and record stores.

Sydney’s Best Coffee

This is where you can get some of the city’s best coffee and chow down on a ramen roll at the Scandi-Japanese Edition Coffee Roasters.

See some of the best international and Australian bands at Oxford Art Factory, or sidle up to a 1920s New York-style wine bar like the brand new Johnny Fishbone, where you’re sure to be served by a tattoo-clad, but friendly-as-hell bartender, eager to recommend some of their tasty bar snacks.

Best Sydney wines and snacks

If you have ever tasted the wines and snacks at Buffalo Dining Club or Chester White, you know you’ll be in for a treat at the owners new Spanish-style tapas enclave.

Wines are sorted about famous artists.

Did we mention the wines are sorted about some famous Johnnys? Jon Bon Jovi, John Travolta, and more.

Sydney Street Art

Be sure to take a stroll down the top end of Goulburn Street, where you’ll happen upon some prime examples of the city’s favourite street artists, like Mulga and Sindy Sinn, or have the chance to go on record-digging at aptly named The Record Store.

Peckish in Potts Point?

Designer shops and more

Thought Melbourne has all the cool laneways? Potts Point, or the Paris end of Kings Cross, is crammed with designer shopping and artisanal delicatessens, and some of Sydney’s best bars and restaurants in a village of beautiful tree-lined streets and one particularly hip and revitalised laneway – Llankelly Place.

Dear Saint Eloise, on the corner of Orwell Street, feels more like you are relaxing in your friend’s dining room with one of the best wine libraries and a selection of tasty bites around. The roe boats, burrata with charred bread and mint, and smoked mussels are simply to die for.

Theatre on the cheap

Take a stroll down Macleay Street and you could think you were somewhere on the Left Bank of Paris. Want to see some great theatre on the cheap? Check out the Darlinghurst, Hayes and Kings Cross Theatres for culture on a budget, and if you plan on getting some work done while in town, check out TwoSpace, where you can work from the rooftop of Kings Cross Hotel.

Exploring Eastside Sydney off the beaten track is a fantastic way to experience a unique side of the city. Here’s a guide to some hidden gems and lesser-known spots:

1. La Perouse

Nestled in the southern suburbs, La Perouse offers a rich mix of history and natural beauty. Explore the stunning Frenchmans Bay and visit the historic La Perouse Museum. The area is perfect for a leisurely walk and some fantastic coastal views.

2. Vaucluse House

This historic estate offers a glimpse into the life of 19th-century Sydney. Wander through the beautifully preserved gardens and learn about the history of this grand house. It’s a peaceful escape from the hustle and bustle of the city.

3. Watsons Bay

While Watsons Bay is known for its picturesque views and seafood restaurants, there are hidden trails and secluded spots to discover. Walk along the South Head Heritage Trail for stunning views of the entrance to Sydney Harbour.

4. Rose Bay

Skip the usual spots and head to Rose Bay’s less crowded areas. Enjoy a quiet stroll along the bay or take a dip at the local swimming spot. The Rose Bay Marina and its surrounding parks offer a relaxing retreat.

5. Centennial Parklands

A massive green space right in the heart of the city, Centennial Parklands is perfect for a day out. Explore the park’s many trails, lakes, and gardens, or rent a bike and discover its lesser-known corners.

6. Bronte Park and Beach

Bronte Beach is often overshadowed by Bondi, but it offers a more relaxed atmosphere. Explore the surrounding parklands, enjoy a swim, or have a picnic with a view. The coastal walk from Bronte to Bondi is also a scenic treat.

7. Paddington Reservoir Gardens

A hidden oasis in the heart of Paddington, these gardens are a great place to unwind. The old reservoir has been transformed into a beautiful urban park with intriguing architecture and serene spots to relax.

8. Art Galleries and Studios

Check out local galleries and artist studios in areas like Surry Hills and Redfern. You’ll find unique artwork and exhibitions that showcase Sydney’s vibrant creative scene away from the mainstream.

9. The Grounds of Alexandria

This is more than just a café; it’s a sprawling space with gardens, markets, and farm animals. It’s a charming spot to enjoy a meal or a coffee while exploring a unique urban setting.

10. Clovelly Beach

For a more laid-back beach experience, head to Clovelly. It’s known for its calm waters, making it perfect for a swim or snorkel. The beach is framed by rocky outcrops and has a lovely, relaxed vibe.

Exploring these spots will give you a fresh perspective on Eastside Sydney and help you uncover some of its lesser-known charms. Enjoy your adventure!

Creative Surry Hills

Sydney famous gay district Oxford Street

Just over the road (Oxford Street) head to Surry Hills, once the home of Sydney’s salubrious set, but now filled to the brim with hipsters, creatives, and organic cafés.

Feeling thirsty? Corner store cum cocktail haven Rosie Campbell’s offers a range of rum-based beverages to what every whistle (perhaps try the epic ‘Rosie’s Coco Colada’ with Pampero Dark Rum infused with Pimento, pineapple, coco lopez, sugarcane, lime, and banana foam).

Crown Street is lined with boutiques, bars, and bookstores, and Surry Hills also has its own art house Golden Age Cinema, and an annual neighbourhood festival – can this suburb get any cooler?

Knowing how many l’s are in Woolloomooloo is the hard bit, but finding somewhere to have a great coffee and a bite to eat is easy. Woolloomooloo has had a somewhat chequered past, filled with tales of travelling sailors, but is now one of Sydney’s fastest changing suburbs.

Best Views of Sydney Harbour

Bordered by the Royal Botanic Gardens, a public pool with the best views of the harbour, and the Garden Island Naval Base (aye aye Captain), the suburb is also home to one of the fanciest and longest wharves in the world. Not only are there several world-class restaurants of the elk of China Doll and Otto, but the Finger Wharf also boasts a newly renovated Ovolo Hotel. The lobby is an Instagrammer’s dream, and rooms are filled with cool art, free goody bags, enough plugs for all your tech needs, and views to kill for.

We don’t want to give all their secrets away, but you should probably ask about the kissing booths and the ‘rockstar’ rooms on offer. Fancy an afternoon snack or something indulgent for breakfast? Check out the local bagels baked in a wood-fired oven sent directly from Montreal–bagels that are crunchy on the outside and soft and squishy inside.

Explore the East Side of Sydney sightseeing

Smoking Gun Bagels offer several treats to get you in the mood–‘Bitch Peas’, ‘Honey I’m Comb’, ‘Miso Hungry’, and the best cream cheese this side of NYC.
Words by Jacqui Smith
Images by Roisin McGee

Off The Beaten Track: Explore the East side of Sydney, sightseeing experience the underbelly and depth of Sydney’s touristy experience.

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