In our ubiquitously connected world, it becomes more and more difficult to disconnect and leave all personal and professional commitments behind while on holiday. Mobile technology allows us to be connected wherever and whenever we want, but at the same time shifts expectations towards constant availability and responsiveness among friends and colleagues. Applying a qualitative research approach, we explored how social and professional commitments influence decisions and experiences of travelers that go on a digital-free holiday. Using the theoretical lens of surveillance, we found that travelers are digitally surveilled not only by their friends and family members on social media, but also by their superiors and colleagues through email and social networks. The expectations of being constantly available and responsive extend into their holiday, which makes it difficult for travelers to truly disconnect and enjoy their digital free travel experience. At the same time, they are inclined to engage in social surveillance of their peers which creates the constant urge to learn about any updates from their private and professional networks. We contribute to the tourism and information systems literature, by explaining how private and professional commitment influence the digital-free travel experience and extend the concept of surveillance to the work context.