Digital nomadism is the reason for the rise in new travel behaviour, particularly the increasing popularity of workations and vacations. Workations (business travellers’ behaviour) is coined by combining work and vacation. Recently, travel trends have changed where working in a usual mode while traveling long-term has become a popular and remote form of work during the COVID-19 pandemic. On the other hand, a vacation trip or the leisure traveller’s journey is based on the time spent away from work or school for leisure or travel. In that case, when it comes to digital nomads, their travel behaviour and work behaviour are interlinked. There are many factors involved in the selection of destinations during workation and vacation modes. This current study intends to identify the key factors that influence travel decisions in both modes among digital nomads. The study also examines the mediating role of financial well-being among digital nomads while making their travel decisions. The research model is tested using SmartPLS and the data collection was through interviews via questionnaire. As a key suggestion from the findings promoting coworking spaces, digital nomad-friendly policies, and tailored hospitality packages blending work and leisure is becoming essential in this new digital era. Enhancing community-building and providing financial incentives can further attract digital nomads and support sustainable tourism development.