Meditation is one of the most widely used psychological tools worldwide, with a plethora of scientific articles documenting its effectiveness and making it an evidence-based practice and method of choice for a variety of mental health problems. However, there are several ambiguities in its approach, noting confusion and alternative use of the terms meditation, mindfulness and transcendence, while the mechanisms and processes of its operation remain unclear. The present research project is a quantitative study that investigated the effects of frequency, duration, total duration and regularity of meditative practices on mindfulness, transcendence and psychological well-being. Overall, the findings highlight the role of meditative experience, particularly stronger engagement in meditative practices. Meditative experience was found to be related to increased levels of mindfulness and associated with all dimensions of mindfulness: increased levels of observability, descriptiveness and action with awareness and lower levels of criticality and reactivity. From the structural equation model tested, psychological well-being is predicted by the application of meditative practices mediated by mindfulness and transcendence. Mindfulness mediates the path from meditative experience to psychological well-being and emerges as a catalyst for the meditative experience in promoting mindfulness and psychological well-being.