Sightseeing Tour Sydney in a Cool Vintage Car

When I think of Sydney Australia, several iconic images come to mind: the Harbor, the bridge and the iconic Opera House, perhaps a Koala or two available for a cuddle at the Zoo. While those spots are awesome, many tourists may be interested in seeing a more ‘local’ side of the city.

While in Sydney, I signed up for unusual day tour called “My Sydney Detour,” a private sightseeing city tour seen in the back seat of a classic 1964 Holden. I’m a big fan of kitsch and car culture, so a city tour in a vintage car seemed like a good fit.

Their mission is to connect travelers with a local slice of life, for a more authentic and immersive vacation experience. Seeing the city through the eyes of a knowledgeable local can open up any destination and take you beyond the tourist traps into the heart of the hidden gems.

Our tour began outside the Old Clare’s Hotel, a urban boutique hotel steps located in the up-and-coming suburb of Chippendale. My guide Richard, a slim Sydney-born entrepreneur with a moustache and a twinkle in his eye, greeted me with a warm smile and a promise to show me some of the city’s best offerings. Over the next four hours we would be experiencing Sydney through the eyes of a local, in the car of a local.

The classic vintage car is affectionally named “Horace, ” with a port sea blue color over ivory cream inteiror. This car was the most popular model produced in Australia. It’s a uniquely Australian car, built by Australians for Australians.

Their goal is to show visitors how to become a local in a day. See where locals live, go to local hangouts, learn about the history (both indegenous and colonial), get the inside scoop on the everyday realities of a local (ie. minimum wage, cost of living, politics, etc.) and get a feel for the three city vibes (inner city, beach and bush).

Highlights of the tour included:

A visit to Bondi and Bronte beaches, sprawling white sands drawing Sydney’s young, beautiful and bronzed, and Chippendale, an up and coming area of the city. This emerging neighborhood far from the typical tourist trail boasts hip hotels in converted brewery spaces, sleek condos with cutting edge designs, and cool contemporary art galleries.

First stop in the Chippendale hood was a look at the Goodsline. This new development took abandonned land that once housed a historic railway and transformed it into a usuable urban space. Much like the High Line in New York City, the Goodsline has expanded into a public, pedestrian-friendly green space.

Next, a stopover at the Powerhouse Museum, which claims the largest collection of Australian artifacts (ranging from steam generators, to guitars from AC/DC, to sketches of the Opera House, to elaborate dresses worn by pop star Kylie Minogue.)

Tummy grumbling, Richard and I took a break from sightseeing to eat lunch at Esther, an unassuming but super trendy foodie spot in a slick grey and glass building set among industrial buildings of Chippendale. We snacked on wood fire pavlova and chatted about local life in Sydney.

Richard, owner and operator of the company, offers several different kinds of tours (“My Moutainous Detour” – visiting the neighbouring mountains), “My Fitness Detour (running tours of the Harbour bridge with a local) and “My Dreamtime Detour” (with a focus on aboriginal spirituality). He explained to me that more and more tourists are opting for travel experiences like this one, that are immersive and give them a chance to connect with the real local people. “Taking a tour run by a local is a way to escape the tourist traps and tap into a vibe of where the local people live,” said Richard, between mouthfulls of roasted Brussels sprouts.

Post lunch we parked the car and continued on our walking tour of Chippendale. My favorite was certainly The White Rabbit Gallery, showcasing installation art pieces from contemporary Chinese artists.

A contemporary art gallery with mixed media owned by Chinese billionaire…pretty cool stuff. The gallery admission is free and exhibits change every few months. I was lucky enough to see an exhibit with a collection of art that ranged from neon light installations to laser light shows. For those who feel a bit puckish post art, there is also a dumpling house attached, where you can snack on noodles and sip back sake or herbal green teas.


Beyond the iconic postcard images of the Sydney habour, much of the city’s charm is found in her neighborhoods. Sometimes the best experiences come from simply connecting with a local, walking the streets and tapping into the pulse of your destination. Just buckle up and let your curiosity do the cruising.

2017-08-03T03:28:56+00:00