Prime Minister Lee Hsien Loong had a spin in a Google self-driving car, and took a ride in one of the latest models of Tesla electric cars on the first leg of his US trip.
While in San Francisco, Mr Lee also met the chief executive of Tesla and SpaceX Elon Musk, Google CEO Sundar Pichai and Eric Schmidt, the executive chairman of Google parent Alphabet.
Mr Lee wrote in a Facebook post on Friday: "We talked about new technologies and global trends, and Singapore's Smart Nation ideas.
"Elon Musk gave me a brief but exhilarating ride in the Tesla Model S P90D, and I also got a spin in Google's self-driving car. :)"
In one of the photos he posted, Mr Lee met Singaporeans working at Google.
PM Lee then spent some time with California Governor Jerry Brown, discussing the Trans-Pacific Partnership (TPP) Agreement and developments in China, he said.
He also met Mr Ian Clark of Genentech, a biotech company with investments in Singapore.
"Ended the day meeting Ian Clark of Genentech, one of the earliest biotech companies. Genentech has a biologics plant in Tuas which they are very pleased with," he wrote.
PM Lee is on a week-long trip to the United States. He is also expected to meet Facebook CEO Mark Zuckerberg and Apple CEO Tim Cook.
After his meetings in the San Francisco area, PM Lee will head to the Sunnylands estate for a special US-Asean summit, which marks the first time the US has hosted a meeting with Asean heads of government.
He is accompanied on the trip by Foreign Affairs Minister Vivian Balakrishnan and senior government officials.