The global pathways that connect cities and nations are congested with people, money, and cultural transmissions. These routes are also hampered by uneven power relations and the efforts of groups to maintain or change them. How do hopes and dreams, feelings of guilt or loss affect transnational migration and the way migrants relate to their environment and to one another? This book is about the migrations and uneven exchanges that bind postcolonial Jamaica to the diasporic city. It is about the desires, intimacies, and power relations that at once inform and reflect transnational migration and the diasporization of urban space. Transnational Yearnings maps a new way to look at contemporary contact zones and global interconnections as it traces circuits of migration and leisure travel between the Caribbean and Toronto, a city that has become for Jamaican Canadians both a place of promise and cultural vitality and a site of criminalization and exclusion through deportation. Transnational Yearnings is an important addition to recent scholarship on Caribbean transnationalism and Canadian-Caribbean relations. By merging the study of large-scale processes, local opposition movements, and interpersonal connections, it paints a fuller portrait than Jamaican immigrants often receive in the media and will appeal to anyone interested in tourism, migration, postcolonialism, and global exchange.