As a Sydney native, I am thrilled when travelers visit my home city. I love sharing off-the-beaten-path tips, there is so much more to see than just the Opera House and Circular Quay. It’s a brilliant city to explore with a significant other. Sydney can be romantic, glamourous, glutinous, arty, active, and everything in between. These are my favourite authentic experiences, as recommended by a local.

1. Take a ferry to Watsons Bay for the best views of Sydney 

Watsons Bay is a short ferry away from downtown. It has lovely bushwalking trails, quiet coves, and great views. After your swim or stroll, head to Watson’s Bay hotel and indulge in a jug of sangria and a bucket of prawns as you ogle the Sydney skyline.

2. Enjoy a day at Palm Beach

‘Palmy,’ as it’s affectionately known by locals, is a coastal suburb at the northern end of Sydney’s beaches. It has a long sandy beach and is known for its calm waves. Palmy is a great place to swim or learn to surf. For sweeping ocean views hike up to the lighthouse, then reward yourselves with seaside drinks at the Boathouse. Palmy is an hour’s drive from the city centre, which helps to keep it off the beaten path.

3. Brewery Crawl around Marrickville

One of Sydneysiders favourite weekend pastimes is brewery crawling around the inner-west. Marrickville is an industrial neighbourhood that’s been recently gentrified and is now one of the coolest suburbs, thanks to the high concentration of breweries. Favourites include Willie the Boatman, Wildflower, Batch, Stockade and The Grifter. As a party of two, you will have no trouble getting a table and might even make some new friends along the way!

4. Surf and explore Manly Beach

Manly is an iconic beach suburb that’s accessible by ferry from Sydney’s centre. The ferry showcases some of the best views of the Opera House and Harbour Bridge as you leave Circular Quay. There are surf lessons at Manly beach and it’s a great locals alternative to Bondi. There are endless restaurants and bars with water views for post-surf rewards. Some standout establishments include Manly Wine, Glasshouse, and Manly Greenhouse.

5. Hop around Sydney’s cocktail bars and Speakeasies

Sydney has had a resurgence of cocktail bars and speakeasies for those who appreciate delectable drinks in intimate settings. Surry Hills and Darlinghurst are at the epicenter of this exciting spirit-forward scene. Brush shoulders with Sydney locals at the Baxter Inn, Stitch Bar, Grandma’s, Eau de Vie, The Roosevelt, and Shady Pines, who often have live music. Make sure to take note of the address, as some of these establishments are well hidden!

6. Bush Walk in Kuring-Gai Chase National Park

Kuring-Gai Chase National Park is one of the only places to experience the true Aussie bush in Sydney. The reserve is full of trails through thick brush, past the odd waterfall, and down to the ocean. If you get lucky, you may even spot a wallaby! Pair your walks with a visit to Church Point, a nearby suburb with two iconic oceanview establishments; Waterfront Cafe and the Pasadena. The national park is also home to one of Sydney’s most exclusive degustation restaurants and boutique hotels, Cottage Point Inn.

7. Enjoy live music & pizza at Frankie’s

Frankie’s is one of the coolest dive bars in Sydney. If you’re looking to impress your partner with some local grit, this will be a winner. Frankie’s serves pizza by the slice and cheap drinks, in a raucous bar with live music every night of the week. Listen to ACDC and Lepellin while you knock back their self proclaimed ‘world’s best pizza.’ Don’t miss happy hour from 4 pm to 6 pm!

8. Chow down on Chinese food

Sydney can thank its large population of Chinese residents for their bustling Chinatown, it’s full of an endless selection of authentic establishments. Hop around and sample dumplings and jianbing, or settle in for a big meal. Some local’s faves include Marigold, East Ocean, and Golden Century. If you’re craving a big brunch try ‘Yum Cha’, which is the equivalent of Dim Sum. It’s perfect for soaking up cocktails from the night before. If you’re after something more glamourous, Mr. Wongs is one of Sydney’s best restaurants.

9. Rent your own boat in Sydney Harbour

Skip the big boats that are overflowing with tourists and bring a picnic aboard your private pontoon. The kicker is that you aren’t required to have a boat license! If you are one of those useful humans who happen to have said license, there are even more options for you. Sydney from the water is a truly magnificent sight, just don’t forget the cheese and crackers!

10. Walk the Spit to Manly coastal path

Skip the uber-busy Bondi to Bronte walk and head to the Spit to Manly coastal path instead. It takes around an hour one-way and is mostly flat with ocean views for the entire duration. Start with a swim or brunch at Clontarf, near the Spit bridge and see some of Sydney’s most expensive homes. Finish up in Manly and enjoy rooftop drinks at Sydney Glasshouse.

11. Indulge in fine dining with ocean views

If you’re a couple of foodies, or you just want to enjoy a special meal, avoid the overinflated tourist traps and head out to one of these gems. Cottage Point Inn is in a remote location within Kuring-Gai Chase National Park. Lunch is the way to go as you enjoy a five-course degustation meal watching seaplanes land on the sparkling Pittwater inlet. Jonah’s is an equally stunning alternative at Whale Beach. If you aren’t up for the two-course minimum at Jonah’s, have a drink at the bar or enjoy the views from the terrace. Reservations are essential at both and each establishment has a boutique hotel for when you decide you never want to leave.

12. Visit Cockatoo Island

Cockatoo Island is a UNESCO heritage-listed island that’s accessed by the Woolwich, Balmain ferry. It’s home to art installations, concerts, and other events including the Sydney Biennale. Take a history tour or enjoy a picnic on the grass. There are plenty of creative activities for a couple to enjoy.

13. Badu Mangroves & Sydney Olympic Park

Sydney hosted the 2000 Games to huge success and the Olympic Park has a plethora of things to do. Including archery, cycling trails, art exhibitions, events, restaurants, and shops. It’s also home to the Badu wetlands with their wonderful walking paths. See how many bird species you can spot within the 40 hectares of parklands and mangroves.

14. Bar hop in Newtown

Newtown is one of the coolest suburbs of Sydney. Think East Village, Brixton, or Brooklyn. It’s covered in street art, unique boutiques, and restaurants with cuisine from around the world. Some of the classic Newtown spots include Continental, Young Henrys, Earls Juke Joint, 1989 Arcade bar, Marys, Tandem, and Bloodwood.

15. Wine tasting

Australia is world-renowned when it comes to our favourite alcoholic vine related indulgence. Sydney’s Urban Winery is a great way to get involved with a tasting without having to travel to the vineyards. They have a wine bar, cellar, and tasting room that features their own wine. Sydney Wine Tasting and GPO Wine & Cheese room are other good options.

16. A day at the Races

Attending the horse races is a right of passage in Australia. It’s not so much to do with the horses, but more so the party and fashion. It is a unique experience to find yourself decked out in your finest livery, drinking champagne in the sun, betting on horses as they race to the finish line, with people screaming all around you, hoping they’ve backed the winner!

There is no doubt that Sydney is one of the most aesthetically pleasing cities in the world, but I hope this article has demonstrated that she is so much more than just a pretty face. Whether you’re foodies, coffee snobs, beachgoers, hikers, fashionistas, or all of the above, Sydney is the perfect place to explore with your loved one.

For more on Sydney, check out my other articles:


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