In this article I examine the settlement experiences of middle‐class Puerto Ricans in the U.S. mainland. Data for the study come from open‐ended interviews with 40 middle‐class Puerto Ricans who came to the U.S. mainland, 20 of whom remained and 20 of whom returned and resettled in Puerto Rico. I examine their subjective interpretations of incorporation and the conditions under which they resettle in Puerto Rico. Findings reveal that in spite of occupational and economic integration into the U.S. mainstream, migration and U.S. settlement result in dislocations among Puerto Ricans, particularly regarding separation from family and kin networks and experiences with racialization and exclusion. Puerto Ricans see themselves as members of transnational families, yet, the struggles of leading dual lives between mainland and Puerto Rican societies result in settlement decisions that reflect desires to live locally with roots in one place instead of feeling split between the two. Experiences with U.S. racism complicate these decisions. Findings illustrate the various patterns of attachments to place, or emotional embeddedness, that impact the circumstances under which Puerto Ricans engage in alternating periods of mainland and Island settlement. The implications for assimilation theories are discussed.