A pilgrimage that began in the cells of the preachers at the Dominican Cloisters of San Marco in Florence seven years ago continues to this day. San Marco was a community ordered to assure the intersection of substantive theology (written and painted) with the realities of human life for the sake of the church’s proclamation. In small, white-washed cells, each member of the Order of Preachers read theology as a form of prayer and reflected on weekly lections through the lens of the fresco that adorned his cell. For hours each day during the summer of 2004, I stared at the same frescoes painted by Fra Angelico, asking myself how each cleric’s proclamation of the Word might have been shaped by the fresco he was assigned for a lifetime. What prompts my return almost a decade later is the relevance of the coincidence between the Dominican reform in the 15th century and my own Reformed tradition in the 16th. Both insisted that the church would be renewed by preaching that was theologically substantive. As a preacher and theologian who also lives at the intersection of substantive theological reflection on Scripture and the realities of human life for the sake of the church’s proclamation, my concern in the 21st century is the demise of theologically-informed preaching and the consequent loss of the church as a theological community. In the years since my summer in San Marco, I have begun to write personal theological essays in response to the frescoes in each cell. My study project would return me to Florence for two weeks. There the mornings would be spent in the cells at the invitation of the museum staff where I again would borrow the frescoes as my hermeneutic for interpreting Scripture and doctrine. In the afternoon, I would pray by reading theology. The remainder of the three months would be spent in Maine continuing my research for and writing of a book on the faith and ministry of a theologically serious preacher.