The first time Mr Muhammad Sufian Mohamed Adam hitchhiked was in Myanmar two years ago.
This time, he is hitchhiking more than 27,000km across 21 countries in Europe and Asia - with the aim of making it home for National Day.
The 34-year-old bachelor put his career on hold three years ago after quitting his job as a fashion designer so he could see the world.
He embarked on this unconventional solo journey last December without much planning. It was not something he initially set out to do.
He told The New Paper in an e-mail interview: "I bought a one-way ticket to London last year simply because it was on promotion, selling at $400 from Kuala Lumpur to Heathrow.
"I spent a week in London and instead of (getting on) a direct flight home, I decided to hitchhike my way back to Singapore ."
He reached Penang on Monday afternoon after hitching a ride in a van.
So he is on schedule to make it back in time to watch the fireworks display at the National Day Parade and end his adventure with "epic pyrotechnics".
He will be going for in-camp training as part of his National Service next month.
His interest in this massive undertaking was first piqued by an online article about a Polish man, Mr Artur Nitribitt, who had made headlines by hitchhiking 25,000km from his homeland to Singapore.
Mr Sufian said: "His story inspired me and challenged me to do even better. I (ended up couchsurfing) at Artur's place and celebrated my 34th birthday with him in his hometown of Wroclaw.
"I travelled in search of a home (that resonates with me). I had lived in Singapore my entire life and was curious if there was a better place out there."
China changed him "as a person" after he was stranded in Lanzhou for two days when no one stopped to give him a lift.
Desperate, he made a sign that said "from Singapore" in Chinese. A car stopped for him within 10 minutes.
He said: "That moment, I realised that being Singaporean is powerful... a luxury. It is always nice to hear locals saying good things about Singapore."
Amazingly, his budget for the trip was just $3,500, and he limited himself to $10 a day for food and necessities. To save money, he couchsurfed, camped and took on odd jobs for extra income.
Despite being weather-beaten and mentally drained from his travels, Mr Sufian is grateful for the opportunity to be a guest teacher for a day.
One of his couchsurfing hosts, a history teacher, asked him to talk about Singapore to his class in Siauliai, Lithuania.
In Surin, Thailand, he volunteered to teach basic English words to primary school pupils using the Singapore flag.
And in Aktobe, Kazakhstan, Mr Sufian - a self-taught artist - ended up being invited by his couchsurfing host's sister, a fellow artist who founded an art studio for people with special needs, to conduct an art therapy session through painting.
Even though he had a few mishaps and found that "dangers lurk in every corner", nothing could contain Mr Sufian's wanderlust.
He said: "I was robbed by homeless kids for a pack of cigarettes in France and pickpocketed (for a power bank) during a carnival in Switzerland. My tent and sleeping bag got stolen in Belgium too...
"(But) most of the time, drivers who pick you up (genuinely want) to help or are in need of a companion on their long journey. Be a storyteller while at it."
Mr Sufian hopes his eight-month expedition will inspire Singaporeans to "switch off the television, pack their bags and start travelling while they still can".
He said: "I may not get to visit fancy museums or monuments, but having that opportunity to be able to meet nice, hospitable and kind people everywhere is monumental itself."
This article was first published in The New Paper. Permission required for reproduction.