I love your response to Generous Boss. I hated Prudie's advice - way to be a serious fun sucker, Dear Prudence! The trip could be amazingly fun, as well as a bonding experience between employees. My company did something similar, an all-expenses paid cruise in the Caribbean, and it was one of the best vacations of my life.

The trip could also be a disaster, but then the LW would know never to do it again.