The Spanish-speaking island of Puerto Rico (also known as Borinquen) has had a complex linguistic landscape since 1898, due to the United States’ colonial imposition of English as the language of administration and education. Even after 1948, when Puerto Rico was finally permitted to hold its own gubernatorial elections and determine its own language policies, controversy regarding how best to achieve bilingualism continued. Despite many studies of the language dynamic of the island, the voices of the people who actually live there have been muted. This volume opens with a basic introduction to bilingualism, with special reference to Puerto Rico. It then showcases twenty-five engaging personal histories written by Puerto Rican language professionals which reveal how they became bilingual, the obstacles faced, the benefits accrued, and the linguistic and cultural future they envision for themselves and their children. The closing chapter analyzes the commonalities of their richly detailed stories as well as the variability of their bilingual life experiences in order to inform a more nuanced language policy for Puerto Rico. The linguistic autobiographies will resonate with bilinguals of all kinds in Puerto Rico and the Caribbean, as well as those in other countries. The main message that emerges from the book is that there are many routes to multilingualism, and one-size-fits-all language policies are doomed to miss their mark.