This chapter is based on data deriving from a larger comparative project on “Caribbean International and Regional Migration: Implications for Development,” which focused on the adaptive strategies developed by Vincentian and Grenadian immigrants in New York and Trinidad and the nature of their ties with their home societies. This project was funded in various parts by the International Development Research Center of Ottawa, Canada, the United States Agency for International Development and the United Nations Fund for Population Activities. Material support was also provided by the United Nations Institute for Training and Research and the Institute of International Relations at the University of the West Indies in Trinidad and Tobago. The larger comparative project was undertaken in collaboration with Dr. Rosina Wiltshire-Brodber of the Institute of International Relations, St. Augustine, Trinidad, and with Joyce Toney of St. Vincent and Winston Wiltshire of Trinidad, whose myriad inputs to the ideas expressed in this paper are gratefully acknowledged. I also thank Colin Robinson, Isa Soto, and Margaret Souza, research assistants in New York, for their insights and observations. Finally, I express my appreciation to Constance Sutton for her many comments and suggestions, and to the many Vincentian and Grenadian immigrants interviewed in New York who generously provided their reflections on their own experiences.