A stressful and unbalanced lifestyle leads to a marked decrease in wellbeing levels from a different point of view. The generation of baby boomers and generation X have suffered more and more from this modern style. Today, generation Y (Millennials) seems to be much more interested and sensitive in this field. They also proactively seek to find an adequate solution by investing one of the most precious personal assets which is their free time. Considering the growing demand for well-being, the wellness economy is becoming more and more popular. It is a market of about $ 4.5 trillion dollars, divided into well-defined segments or macro-areas market, steadily growing from 2015 onwards. The boundaries are difficult to define today due to its numerous cross-growth opportunities. After a wide description of the wellness economy, this paper focuses on introducing the role of connected fitness to analyze its component and dynamics. Using a case study methodology, supported by a SWOT analysis, two of the most relevant players in this market were analyzed based on strengths, weakness, and future developments. The results show a situation where the two competitors are balanced and have a clear strategy for their expansion, even though they cannot count on all customer groups.