Pucker up and get ready to swoon, we’ve selected the best bars, restaurants, cafés and amorous activities in the city, to help you decide where you’ll be headed on your first date.
These bars really set the scene for a first date. We’ve picked the spots – now all you have to do is pick the vino!
Well-hidden at the back of the Kirketon Hotel, this secret speakeasy will whisk you back in time to the roaring ‘20s. Settle into a leather booth, soak up the smooth jazz soundtrack, and work your way through the deliciously moreish cocktail list, while you get to know each other intimately. If you really like your date, you can ask your waiter to crack open the ‘personal drinks cabinet,’ which houses the bar’s priciest drops.
229 Darlinghurst Road, Darlinghurst
Tucked away in a Paddington terrace, this bar ticks all the boxes for a first date: it’s small (be sure to make a reservation), dimly-lit and incredibly chic, and has a wine list that doubles up as a conversation starter. Order a bottle of red or sip on something new (like orange wine) and then swap stories over a few share plates. Leave space for the fabulously fluffy tiramisu. The ultimate date night dessert.
10 William Street, Paddington
Inventive cocktails and an impressive wine list make this intimate restaurant a date night favourite. This much-loved haunt whips up bar bites and small plates perfect for sharing, but the food is that good you might not want to (if you do – it must be love). If you opt for a table inside, expect dim lighting and lots of cosy nooks, or take a streetside seat for that European alfresco dining experience. Swoon.
24 Young St, Neutral Bay
Nestled in the leafy streets of Potts Point is Rosé Royale, the world’s first rosé wine bar. The interiors are luxe with leather booths and marble tables. But the pièce de résistance is its cosy courtard, complete with fairy lights, blankets and a swinging chair for when you want to cuddle up to your special someone. For a night to remember, go all out with their Rosé Degustation – you won't regret it.
7 Kellett Street, Potts Point
With their impeccably smooth service, these restaurants have got you covered. That means you can spend more time getting to know your date, and less time umming and ahh’ing about the menu.
Homely and chic, A Tavola is pasta heaven, and the perfect spot a first date. Choose a seat in the garden courtyard or inside in the charming dining room, tuck into pasta that’s been handmade a few minutes before it lands on your table, and imagine you're on date night in Italy. Our advice? Pair your meal with an Italian wine and save room for dessert.
348 Victoria Street, Darlinghurst
Offering over 100 seasonal cheeses and 250 wines, cheese lovers are spoilt for choice at GPO Cheese and Wine Room. With stone walls, dark timber furniture and plenty of tables for two, this sophisticated underground restaurant is a date night dream. Depending on your date’s taste you can create your own board or dine from one of their popular cheese flights paired with three wines or whiskeys.
8 LGF, Lower Ground Floor, Sydney GPO Building
An Eastern Suburbs hotspot, Bar Machiavelli provides a doze glitz and glamour – all you need to bring is your date and a healthy appetite. There's lots to experience while dining, from the glass walled kitchen to the montage of black and white photos artistically projected onto the walls. The antipasto and fresh pasta are among their most popular menu items, with the tiramisu martini an essential after-dinner treat.
10 Nield Avenue, Rushcutters Bay
Who said dates had to be of the night-time, tablecothed variety? We’re suckers for a good brunch date – they’re unpretentious, fun and a lot more casual for an initial rendezvous.
With wall-to-wall books and plush velvet chairs, this hidden gem café-slash-bookstore is as cosy as it gets. Gertrude & Alice offers a range of snacks and drinks – ideal for a bite to eat and a chat in an unhurried environment. If you’re craving a quieter vibe, head to the Hemingway room, a beautiful hideaway with sofas to nestle into with your date.
1/46 Hall Street, Bondi Beach
Treat yourself (and your date) to alfresco dining with a view at this Lower North Shore brunch haunt. Sitting pretty next to the wharf, you’ll watch the sailboats drift by as you nosh on seriously tasty brekkie options, like the Apple Bircher or the Smoked Salmon Fritters with Caviar and Poached Eggs. Keep the healthy vibes going and do the picturesque hike from Balmoral Beach to Chowder Bay. If that’s not your scene, grab a smoothie to go and hit the beach.
2 The Esplanade, Mosman
You and your date are going to want to snag a window seat at this floating café – yes it’s floating and it’s as awesome as it sounds. It’s lined with floor to ceiling windows and a charmingly rustic, nautical décor. Situated on the Kirribilli ferry wharf, the quaint café may be small but that just means you’ll be closer to your date (which isn’t a bad thing).
Kirribilli Commuter Wharf, 1/2 Holbrook Avenue, Kirribilli
Fancy something a little more adventurous? Be it a secluded beach or a trendy art-gallery, there’s something suited for every type of rendezvous – so get canoodling!
Grab your date and head to one of Sydney’s many waterfront parks for a DIY, BYO picnic to remember. One of you can look after the drinks, the other can look after the bites, then let the dreamy locations do the rest. Our pick: Head to Wendy’s Secret Garden in Lavender Bay: a magical little oasis with plenty of picturesque corners to explore.
Sydney is full of hidden beaches for those dates where you want something a little more secluded. Grab your swimmers and some snacks and sneak away to one of these quiet locations. Head to Collins Flat Beach in Manly which is only accessible by a walking trail, or Parsley Bay in Vaucluse for a picture-perfect date with crystal clear water (not to mention the beautiful waterfall).
Head to a Retro Cinema
For a movie date with a touch of something special, head to one of Sydney’s historic cinemas to see a film with a side of nostalgia. We love The Orpheum in Cremorne – an Art Deco cinema with beautiful architecture and pre-show live music on weekends, courtesy of the resident organ player. Another favourite: the Golden Age Cinema and Bar in Paramount House, which will have you and your date step back in time in the intimate setting of the cinema. Follow the movie with a cocktail in the cinema’s glamorous bar (we love the Maple Pecan Old Fashioned).
Get Lost in a Gallery
To us, there’s nothing better than getting lost in a gallery and admiring art all afternoon with someone you’re into. Our pick for date night is the Museum of Contemporary Art at The Rocks, especially on Wednesdays when it’s open until 9pm for Lights on Later. Hear talks from artists, get hands-on with workshops, or take a guided tour from a curator. Afterwards, wander up to the Sculpture Terrace overlooking the harbour and wind down with live music and a glass of wine.