There has been a link between spirituality and learning throughout the Middle Ages, from the first monastic schools, to the rise of the cathedral schools and finally with the development of universities. There are differences between monasticism and scholasticism but there are also movements where these two perspectives converge. In this paper I will provide an overview of monasticism and scholasticism during the medieval period, describing their differences and then going on to discuss two movements, the Dominicans and the Brethren of the Common Life, where spirituality and learning come together. Finally, I will conclude with reflecting on how spirituality might be fostered through learning today.