Four MBTA and MassDOT honchos — apparently undeterred by a financial crisis and angry protests over outsourcing jobs — took off this week for a five-day, taxpayer-funded transit conference in San Francisco featuring kayaking, a chocolate and coffee tour and a karaoke party, the Herald has learned.

The four state officials, including one of the architect’s of Gov. Charlie Baker’s financial reform plan, MassDOT Assistant Secretary for Policy and Planning Kate Fichter, racked up at least $5,600 in expenses for airfare, hotel rooms and other costs, according to an MBTA spokesman.

The “Rail-Volution” conference in San Francisco kicked off on Saturday with a “Chocolate-Coffee” biking tour and a trip to Alcatraz and wrapped up yesterday — at the same time union leaders and Democratic lawmakers held a raucous rally outside Faneuil Hall to denounce Baker’s plan to replace some MBTA workers with private sector companies.

The West Coast trip by top state officials on the taxpayer dime comes at an awkward time for the Baker administration, which is defending privatization and a nearly 10 percent fare hike imposed this July as necessary to keep the T financially afloat.

The Carmen’s Union president and six other workers were arrested last week in a protest over the T board’s vote to award a $19 million contract to a private security firm to replace union workers at the infamous “money room,” where cash from fare machines is counted.

Besides Fichter, one of Baker’s top reform leaders, three top MBTA officials also attended the San Francisco conference: director of real estate Janelle Chan; director of development Mark Boyle and deputy general counsel Lauren Armstrong. An MBTA real estate consultant also traveled with the group but his costs were not paid for by the T or MassDOT, officials said.

MBTA spokesman Joe Pesaturo said costs were kept down because the conference fee was waived for two of the officials, while Chan stayed with family in the Bay Area.

Pesaturo defended the trip, saying “Rail-Volution” is a “well-respected” organization and several of the state officials led some of the many workshops at the conference, which focused on building livable communities and other topics like bike sharing and environmentally sustainable transit.

“As the Commonwealth’s second largest land owner, the MBTA is constantly working to maximize its real estate assets and promote and advance economic development along its vast network of commuter rail and subway stations,” Pesaturo said in a statement.

“Understanding the link between land use, transit and development is critical to creating jobs, housing, and new business, and attracting more riders to the MBTA.”

But there was also plenty of time to network and party, according to the conference agenda. Among the social activities were a morning kayak trip, a tour of the infamous Alcatraz prison, a “Pecha Kucha Slam” at the Great American Music Hall and a welcome party sponsored by Morgan Stanley that featured the “Amazing Embarrassonic Human Karaoke Machine,” where conference guests were invited to sing along to a live band.

Sources said the conference trip was approved by Secretary of Transportation Stephanie Pollack, who has been in the middle of Baker’s privatization and cost-cutting reform measures.