Shipping is a highly cyclical, volatile, and unpredictable industry. In recent history, economic shocks like the COVID-19 pandemic have heavily disrupted supply chains and tested the resilience and adaptability of shipping lines from both operational and financial perspectives. Therefore, the commercial success of shipping lines is increasingly determined by an optimal balance between reliable logistics operations and financial performance. Given this, chartering strategies of shipping lines are pivotal in achieving fleet optimisation and financial sustainability. Using a Mann–Whitney U test and a data envelopment analysis (DEA), this study provides a view on chartering strategies and efficiency levels of shipping lines in response to the COVID-19 pandemic. The findings reveal that chartering strategies have changed considerably since 2020 and that most shipping lines have pursued a peculiar strategy with a different mix in terms of chartered vessels’ size, age, and period of charter. Shipping lines which showed the most marked differences in chartering strategies also yielded higher efficiency scores under DEA, whereas those that did not sustain large changes scored lower in terms of efficiency. This study provides significant insights on and managerial guidance for understanding and benchmarking chartering strategies and their impact on efficiency gains.