Throughout the sixteenth century, the Order of St John sought to redefine its place in a constantly changing world to survive, weathering storms from within and without. Existing scholarship largely focused on the institutional, legal, and administrative tools that it used to carve a space for itself in the world, yet the devotional-spiritual dimension has largely been left unexplored. The study of the ‘faith of the knights’ does not just concern the knights or the island of Malta but engages a wider scholarship as a micro-study of early modern piety, religion and spirituality. This study has attempted to decipher the effect that membership in the Order had on an individual’s faith and personal spirituality. It considers both the Order as a sum of its individual members, as well as an institution. The emergence of a Borromean retreat-house for knights in Valletta, in the immediate aftermath of the Council of Trent, was an indication of the desire, at least among some members, to live their vocation in a different manner. Consequently however, the existence of an alternative way of life for the Hospitallers, one that was supposedly closer to the spirit of Trent, questioned the existing interpretation of the Order’s spiritual charism, and became a source of disagreement. The resulting compromise was a spirituality that was personalised rather than institutionalised. What changed in the approach towards Hospitaller spirituality in the decades that followed, was the growing recognition by the institution itself, that the Order of St John had multiple vocations. To this end, the Order became a melting pot of spiritual traditions, to a point that it would be more accurate to speak of Hospitaller spiritualities, in the plural rather than singular. The downside was a process that was oftentimes inconclusive or incomplete. These considerations hope to place the Order of St John alongside other Catholic religious orders of the Counter-Reformation period, not merely as a military force engaged in religious warfare, but also as a religious entity that reacted, adopted and at times challenged the precepts of a wider Catholic Church.