The challenge will continue until June 22 and aims to help city officials gain familiarity with public transit and inspire them to improve the experience.
"I wouldn't say they are out of touch," explained Transit Union Board Member Peter Straus. "But we want to make sure that they really understand it on a gut level what it means to users on a daily level."
Riding Muni is something he says Supervisors should be doing anyway, thanks to a 1993 police under Proposition that stipulates city officials should ride the city's transit system to and from work at least twice a week.
Day 1 began with several supervisors taking part. All tweeted about their adventure using the hashtag #onboardsf.
Supervisor Jane Kin says she took the 19 Polk to go three stops to City Hall and got a lesson on how long riders sometimes have to wait.
"Instead of 15 min walk, I did 21 min wait. Guess I'm late," said Kin.
Even the mayor took to Twitter Monday, tweeting a photograph documenting his ride on Muni prior to unveiling his two-year proposed budget for all city departments.
The mayor tweeted, "On our way to City Hall!" shortly before 8:30 a.m..
Supervisor John Avalos also had some trouble. He tweeted "I believed the next Muni sign and got on K by accident. Have to walk back and catch BART."
It's a familiar story for riders who use Muni every day. KTVU also got onboard and talked to several who say they want to make sure the supervisors get a real look at what they deal with.
"I want them to be on at the worst possible time," one rider told KTVU.
John Lovano who rides everyday said, "I do see glitches on some of the lines, the Mission line is very, very overcrowded."
SFMTA spokesperson Paul Rose said changes are coming.
"We are doing a good job at doing better at what we do. Our biggest room for improvement is our reliability," said Rose.
Supervisor Scott Weiner stood with fellow members of the board and with public transit enthusiasts outside San Francisco City Hall this afternoon and said his first day of public transit, although he is a regular daily rider already, was a success because it got him thinking about possible solutions.
Weiner said public transit impacts the city's economy and residents' quality of life. He said that the challenge brings public transit much needed attention.
"We are moving in a positive direction," Weiner said.
Transit supporters also gathered on the steps of City Hall and held signs with slogans championing Muni, such as: "Save the world, Ride a bus."
Many of the supervisors, such as Eric Mar vowed to take the challenge seriously and said they will stick to the challenge despite the difficulties it sometimes presents.
Nicole Ferrara, the executive director of the pedestrian advocacy group, Walk San Francisco, encouraged city officials as they went on their journeys across the city to consider solutions to safety issues they see and to make policies that address the inadequacies they detect.
Ferrara said these trips "can help shape future policies" that can improve or even save lives.