Contemplating a date night? Whether you're looking to impress someone new, surprise your loved one, or screenshot some ideas for later, the lower North Shore of Sydney has plenty of options if you know where to look or who to ask. In this case, how lucky you asked us!

Here are some top recommendations (that aren’t the Oaks) from a long-time local:

🚣‍♀️ Sunset kayaking through Lavender Bay

For an enchanting evening, rent a kayak from Lavender Bay Kayaking at around 5pm on a calm weather day (during Daylight Savings) and paddle back to enjoy a sunset picnic or a walk along the foreshore and into Wendy Whiteley’s garden. 

🍸 🍝 Cocktails and Italian in Kirribilli

While you’re in the Kirribilli area, take your date to The Botanist for a cocktail or two before heading to La Capannina for a night of Italian classics in this glass-walled restaurant with Harbor views. Or… let the dimly lit atmosphere at the Botanist tempt you into staying put all evening. It’s very easy to lose track of time there - in the best way.

💎 Spend an evening checking out the hidden gems of Waverton

Waverton is an undersung date night spot. With plenty to discover along its foreshore like the intriguing grounds of the Coal Loader, marinas and stunning lookouts, start or end at Bar Quattro - a lively and moody bar by the train station - and go from there and aim for Berry’s Bay Lookout.

You can also grab a bottle from Liquor and Co. and a charcuterie board from Giuseppe’s Gourmet Meats and be set for the night. (Don’t tell anyone we told you, but there are also publicly available kayaks positioned around Waverton. Just be sure to return them to where you found them.)

🍛 Grab a curry in Cammeray

For flavour-seekers: Don’t Tell Uncle in Cammeray is a spacious downlit Indian restaurant owned by the proprietors of Surry Hills’ mainstay Don’t Tell Aunty. If you’re lucky you can grab the table by the ornamental fish tank for the Baz Lurhmann vibes. They also have a fantastic range of craft beer and cocktails including popular house originals as well as a subsection called “The Crazy Stuff” including Bollywood Breeze and a Passionjito.

🚶Take a historic walk through North Sydney

Nothing bonds people like shared stories and a little adventure. If you’re into your local history (make sure your date is too!), grab one of North Sydney Council’s History Walks brochures and discover your area together on an early evening walk. There’s a guided walk for every area I’ve mentioned so far, but the Cremorne Point one will allow you to take in the best sights of the harbour and the city skyline as it lights up for the night. I don’t have to tell you to pack a picnic.

Of course, nobody’s stopping you from reading these guides yourself and impressing your date with your local knowledge. We won’t judge you.

🕯️🍷 Finally, if want somewhere with a sophisticated ambience, here are the honourable mentions

Enoteca at Neutral Bay for a curated wine list and thoughtful Italian

No. 32 in St. Leonards for a delicious approach to “honest” Japanese and Middle Eastern cuisine.

Nico in Cammeray: “The sort of neighbourhood Italian you want in your own neighbourhood.”

Jizakana in Cammeray for Japanese delights, from sushi to wagyu beef.

Antica Dining, North Sydney, a hatted restaurant with an endless list of mouth-watering dishes.

Genzo in North Sydney for flame grilled meats and hand crafted noodles.

Image Credit: Lavender Bay Kayaking / Antica Dining Instagram