This paper explores the lives of “liveaboards” in the Mediterranean; people who travel, work, and live on sailing boats. It starts from the premise that these individuals’ and groups’ “quest for a better life” should not be treated as an elite phenomenon that exists in the vacuum of wider social, political, and economic relations, but is part of the wider story of the 21st century. The paper presents the expectations and experiences of maritime lifestyle migrants, how their stories develop over time in the course of their personal life, but also in relation to sudden recent events and changes such as Covid-19 and Brexit. The introductory sections are followed by two ethnographic portraits to showcase the complexity of maritime lifestyle migration, specifically concerning notions of stillness and movement. The portraits are written in a creative non-fiction style, a form that brings to the fore emotional and everyday details, as well as atmospheric descriptions that allow us to “inhabit the problem.” The two portraits are followed by a discussion on the circular stillness that focuses on biographical details of maritime lifestyle migrants in a longitudinal perspective, highlighting the processual and often unpredictable nature of maritime lifestyle migration.