Briton Nathan George grew up listening to his grandfather's stories about driving from London to Singapore with his friends in 1955, so it was an easy decision to join an expedition that recreates the original jaunt, albeit in reverse.
Mr George, 21, is one of eight adventurers embarking on the gruelling trek that will take three vehicles from Singapore to London, traversing jungles, mountains and deserts across three continents.
The 100-day journey was flagged off at the F1 Pit Building yesterday.
"My grandpa was fresh out of university when he set off, just like I am right now," said Mr George, a Newcastle University economics graduate. "He has always talked about his trip so it's exciting to go off and do it myself even though I have no idea what to expect."
His granddad Tim Slessor, who was 24 when he made the trek - dubbed "The First Overland" expedition - is now 87.
Mr Slessor took ill the morning of the flag-off but is expected to join the team on the road shortly as the ninth member.
In 1955, six Oxford and Cambridge university students, including Mr Slessor, made history when they arrived in Singapore after six months on the road - the longest overland expedition at the time.
A restored dark-blue Land Rover Series I named "Oxford", used in the original expedition, is one of the three vehicles on this trip.
Two other surviving members from the expedition 64 years ago - Mr Nigel Newbery, 86, and Mr Patrick Murphy, 88 - were at yesterday's flag-off.
Mr Murphy said: "We had only an out-of-date map and compass to guide us; there wasn't a GPS or even mobile Wi-Fi at that time. At some points, we were completely cut off. Now they've got it good."
The team on this trip - called "The Last Overland" as a homage to the earlier journey - includes Singaporean Larry Leong, 51, a part-time IT consultant and no stranger to long road expeditions.
In 2015, Mr Leong, his wife Simone and their then five-year-old daughter Lucy took a 20,000km trip, driving from Singapore to London via Russia, Scandinavia and the Arctic Circle.
He had previously driven from London to Kuala Lumpur and then on to Singapore in 2007.
"Group dynamics will be the hardest part. We'll have to learn how to adapt and live together for the next three months but, when you go on the road like this, these are friends you'll make for life," said Mr Leong.
The send-off fanfare included an escort to the Woodlands crossing point into Malaysia by a convoy of around 90 Land Rovers driven by local enthusiasts, including members of the Land Rover Owners Singapore club.
The epic journey will be documented, an effort led by British film-maker Alex Bescoby, 31, who is a core member of the team.
The Last Overland is supported by the Singapore Tourism Board and British auto manufacturer Jaguar Land Rover, among others.
Madam Tay Gek Thin, 78, was one of the people at the send-off.
She had met Mr Slessor and got his autograph when he visited her school, St Margaret's Secondary School, in 1956 to talk about his experience.
She said: "They were so brave to go into the unknown right after graduation back in the day. They roughed it out and did an amazing job. Now it's the new generation's time to keep up the adventurous spirit."
Correction note: This article has been edited for clarity.