We lived out our ‘Roman Holiday’ fantasies by taking a tour around S'pore on Vespa scooters

Complete with red lips, oversized sunnies and pretentious neck scarfs.

| Melanie Lim | Sponsored | July 09, 2022, 11:55 AM

Picture this: you’re a beautiful princess from an unnamed European nation on a state visit to Rome.

Frustrated by your tightly scheduled life, you secretly leave your country’s embassy and spend the night at a handsome American reporter’s apartment.

The next day, he offers to show you around Rome but you decline, instead opting to explore an outdoor market and get your hair cut.

Coincidentally, you meet that handsome reporter again, this time at the Spanish steps, where he convinces you to spend the day with him.

“Live dangerously. Take the whole day.”

You and him recklessly drive through traffic on a Vespa scooter and subsequently explore the city, ending the day off with a kiss and a tearful farewell as you resume your duties as a princess.

Roman Holiday

If the above sounds vaguely familiar, that’s because it’s a brief synopsis of the 1953 American romantic comedy “Roman Holiday”.

Those of a certain vintage may recall this critically acclaimed film which stars the ever-regal Audrey Hepburn as Ann, the princess-gone-rogue, and the dashing Gregory Peck as expatriate reporter Joe Bradley.

While neither a film of my age nor time (I’m a 90s baby), I know a good film when I see one, let alone this Hollywood classic which - safe to say - transcends generations.

So when my colleague Winnie offered me the chance to live out my “Roman Holiday” fantasies by going on a Vespa tour around Singapore one weekday afternoon, I jumped at the chance.

Exploring Singapore in a Vintage Vespa Sidecar

Explore Singapore in a Vintage Vespa Sidecar is a landmark tour by social entrepreneurship Singapore Sidecars.

As its name suggests, the tour brings customers around heritage areas like Kampong Glam, Little India and Chinatown, as well as other sites such as the iconic Marina Bay Sands hotel and the Civic District in a vintage Vespa sidecar.

According to co-founder Simon Wong, the sidecar fleet had been engaged in fundraisers since 2012, just a few years after Wong lost his wife to cancer.

In 2018, it became a social enterprise after a fundraiser for the reconstruction of earthquake-stricken Nepal.

As word got round and the tours started increasing in popularity, they eventually caught the attention of the Singapore Tourism Board, who supported them with heavy marketing.

Now, Wong’s Vespa tours are so acclaimed that even Joe Russo, the film director of Avengers: Infinity Wars declared it “the best tour I’ve ever been on” when he came to Singapore in April 2018.

And with good reason, of course.

I mean, who wouldn’t want to soak in the sights and sounds of heritage areas and admire the slick Singapore skyline, whilst being zipped around on an open-air Vespa sidecar?

The Tour

We started our tour with a brief overview of the places we’d be visiting, followed by some shots with these red and silver vespa scooters at the entrance of Capitol Theatre.

While neither princesses nor in Rome, Winnie and I got our game face on by dressing up in “Roman Holiday” inspired outfits, complete with red lipstick, oversized sunnies and pretentious neck scarfs.

Winnie and I

It was a pity that we didn’t have our own ‘Joe Bradley’ to travel around with, but we enjoyed each other’s company nevertheless, as well as the ‘princess’ treatment we got.

Our tour guides for the day, Wong and lead rider Yusri Sallim, were extremely accommodating throughout the “photoshoot”, guiding us on the best poses and angles we could adopt at different landmarks.

Wong and Yusri

(Thanks to them, I managed not to look too much like a wrapped dumpling in all the photos we took.)

For the record, here’s a list of the places we visited (in sequence):

  • Victoria Theatre and Concert Hall
  • Sultan Mosque
  • Haji Lane
  • Esplanade Jetty

This is what we learned at each pit stop.

Victoria Theatre and Concert Hall

Situated along Empress Place, Victoria Theatre and Concert Hall is a performing arts centre gazetted as a national monument on February 14, 1992.

Making sure to get a “heart” sign in the photo.

It is a complex of two buildings and a clock tower joined together by a common corridor; the oldest part of the building was built in 1862, and the complex completed in 1909.

The building was constructed during an era of Victorian Revivalism that was popular in Britain at the time, and its design reflects this architectural style.

During World War II, the memorial hall was used as a hospital for victims of bombing raids by Japanese forces.

When we arrived at this pit stop, I was impressed by how well the theatre and concert hall blended with the other hyper-modern buildings surrounding it, as well as the rich history behind its walls.

Just as Ann and Joe toured the Roman Colosseum and savoured its fascinating heritage and gorgeous architecture, we too revelled in the beauty of this famous landmark.

Sultan Mosque

Next up, we coasted along the roads and landed outside Sultan Mosque.

With its massive golden domes and huge prayer hall, the impressive Sultan Mosque is a must-see if you’re in the historic Kampong Gelam district.

We discovered that the mosque was built for Sultan Hussein Shah, the first sultan of Singapore, back in 1824.

After a hundred years, it was redesigned into the present mosque by Denis Santry from Swan and Maclaren, Singapore’s oldest architectural firm, and rebuilt in 1932.

With the help of Wong and Yusri, we took some shots at the archway which led to the mosque's entrance.

Haji Lane

After snapping away, we continued our tour by cruising into the hipster street of Haji Lane.

Quite possibly one of the narrowest streets in Singapore, this back alley is filled with 19th-century shophouses now home to cafes, bars, lifestyle shops and indie boutiques.

I thoroughly enjoyed the ride down here, doused with quirky fun and many Insta-worthy photo opportunities.

Esplanade Jetty

Last but not least was a stop over at the very end of Esplanade jetty (in between Makansutra Gluttons Bay and The Float @ Marina Bay), where we had an expansive view of Marina Bay Sands, the ArtScience Museum and the Central Business District.

This was probably one of my favourite parts of the tour because of the unobstructed view we had of the city skyline, as well as how harmonious a photo Wong helped us snap of MBS, the ArtScience Museum and the CBD skyscrapers.

If you want to see Singapore through a different lens, or even just soak in the beauty of our city-scape as a local/tourist, this spot will definitely not disappoint.


After approximately one and a half hours, we ended our tour and headed back to where we started - Capitol Piazza.

Even before Wong had the chance to debrief us, I was completely sold on the experience.

Unlike tours of Singapore by car, this Vespa tour allowed us to explore less travelled paths in open-air, with the ease and convenience walking tours may not be able to provide.

I also got to imagine how it must have felt like for Ann and Joe to scoot around the city on a Vespa scooter with brand new eyes and a tourist’s perspective.

If you’re interested in recreating a “Roman Holiday” experience of your own right here in Singapore, you’ll be pleased to know that this tour is one of the many activities curated by travel experiences platform Pelago.

For the uninformed, Pelago by Singapore Airlines curates a wide selection of travel experiences, both in Singapore and across more than 40 global destinations.

Users can easily earn and redeem KrisFlyer miles with every booking on the platform.

From now till July 31, they are having a S$40 discount with every S$100 spent on all experiences sitewide using the promo code GOTRAVEL40, terms and conditions apply.

Those who are planning to book their next holiday soon can also click here to explore more on Pelago.

This sponsored article by Pelago allowed this writer to feel like a princess-gone-rogue for an afternoon.

Top images via Paramount Pictures and Melanie Lim