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Located in the heart of Sydney, the neighbourhoods of Woollahra and Paddington stand out from the crowd with culture, sophistication, and natural beauty seamlessly blended. These two areas, steeped in history and contemporary charm, have much to offer for those seeking an authentic Sydney experience.

As you embark on your exploration of Woollahra and Paddington, imagine yourself strolling through picturesque tree-lined streets, discovering hidden gems at every turn. From world-class dining establishments to captivating art galleries and tranquil parks, this guide will lead you to the treasures that make these neighbourhoods so exceptional.

Whether you're a food enthusiast, an art aficionado, or simply seeking a peaceful escape, these neighbourhoods have something for everyone. Join us as we delve into the heart of Woollahra and Paddington, where the past and present meet to create an unforgettable journey of discovery.

The Essentials

QE Foodstores
364 Oxford St, Paddington

Maloneys Grocer
68 Moncur St, Woollahra

Wholefoods House
112 Queen St, Woollahra

Simon Johnson
55 Queen St, Woollahra

Paddington Compounding Pharmacy
322-324 Oxford St, Paddington

Bake Bar
226 Glenmore Rd, Paddington

Jim's Cellars
41 Ocean St, Woollahra


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10 William Street

Nestled in the heart of Paddington, 10 William Street is a haven for wine connoisseurs and food lovers alike. Savour exquisite Italian-inspired cuisine and an extensive wine list that caters to every palate. The cosy ambiance makes it perfect for an intimate dinner or a relaxed evening with friends.

10 William Street, Paddington

St Peter

Just a stone's throw away in Paddington, St Peter offers a seafood experience like no other. Feast on exceptional quality seafood in a sustainable, ‘fin to scale’ setting - with signature dry aged dishes and the name of the fisherman who’s made your catch. The ever-changing menu ensures that every visit is a delightful surprise.

362 Oxford St, Paddington

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Chiswick Restaurant

Enjoy garden dining at its best at Chiswick Restaurant, where farm-to-table meets garden elegance. Set within the lush Chiswick Gardens, choose from a seasonal menu that celebrates the freshest produce available to create deceptively simple, impactful and deeply flavoursome dishes.

65 Ocean St, Woollahra


Barbetta transports you straight to Italy with its authentic Southern Italian dishes. Dine al fresco on the charming terrace or savour traditional dishes indoors. The star attraction? A selection of artisanal house-made pastas, complemented by an extensive wine selection. Whether it's a romantic evening or a special celebration, Barbetta ticks all the boxes for a memorable meal.

2 Elizabeth St, Paddington

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Cipri Italian

It may be a fine-dining, napkin-on-your-lap kind of restaurant but with Cipri’s five-star food and moody ambience comes the welcoming, unwavering Italian hospitality of the three Cipri brothers. And with the kitchen headed by inspired and talented chef Alessandro Cola, the Cipri experience is one that will keep you coming back for more.

10 Elizabeth Street, Paddington


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Centennial Park

When you need a break from city life, head to Centennial Park. This expansive urban park is perfect for picnics, leisurely walks, cycling, and even horse riding. It's a serene oasis in the heart of the city. Make sure you check the website for a calendar of events during your stay.


Paddington Markets

Dive into the vibrant atmosphere of Paddington Markets, where local artisans and designers showcase their creations. From fashion to art, jewellery, and unique crafts, you'll find one-of-a-kind treasures to take home. Plus if you’re keen on fresh florals, stock up on beautiful bunches to add a little colour to your stay.

Every Saturday from 10am

395 Oxford St, Paddington

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Art2Muse Gallery

Explore Sydney’s vibrant arts scene with an eclectic collection of artworks from both emerging and established Australian artists. Traditional techniques, modern interpretations, and a rich cultural tapestry come together to create a stunning and thought-provoking experience. Expect a wide range of artistic mediums, including paintings, sculptures and photography to keep you inspired year-round.

234 Jersey Road, Woollahra

Parlour X

Aside from being the eastern suburbs’ premier designer fashion destination, Parlour X is an architectural gem and style frontrunner. Nestled inside a stunning revamped period home, with floor-to-ceiling windows displaying their couture, and exposed brick for extra flair, every inch of the store screams ‘pretty’. Stocking everything from local luxe Australian labels, to established European fashion houses like Fendi and Saint Laurent, it is a must-visit for every fashion lover.

The Church, 261 Oxford St, Paddington


The Intersection

Perched elegantly on the intersection of Glenmore Road and Oxford Street, this aptly named shopping strip is the style destination for Australia’s premier labels. Get back in touch with the romance of boutique shopping down tree-lined streets dotted with laneway cafes as you get to know some of Australia’s most successful up-and-coming designers, from Zimmermann to Manning Cartell to Scanlan Theodore

Cnr Glenmore Road & Oxford St, Paddington

Ampersand Café & Bookstore

Books, food and coffee – what more could you want? Cosy up at Ampersand Café & Bookstore with brunch and a latte, surrounded by tomes new and old, with a warm laneway atmosphere to add to the utter cuteness of the experience. A perfect first date idea, or a fun experience to share with friends; either way it is a must-try.

78 Oxford St, Paddington




Chauvel Cinema

Heritage listed and loved for 40 years by Paddington locals, the Chauvel Cinema is one of Sydney’s most popular homes of independent, world and cult film culture, alongside showing regular blockbuster favourites.

249 Oxford Street, Paddington