This chapter seeks to provide new insights into the promulgation and effect of the Constitution of Cádiz in Cuba and Florida. While Havana and St. Augustine were both part of Spain’s expansive Caribbean colonies, St. Augustine was militarily, politically, and economically dependent on Cuba during the early nineteenth century. The two locales were socially quite different: Havana was wealthy, closely tied to the peninsula, and replicated the common aspects of Spanish colonial society. By the early decades of the nineteenth century, St. Augustine outside its fort, the Castillo de San Marcos, was poor, sparsely populated, and socially mixed. This lack of resources and personnel led St. Augustine to modify or to improvise when complying with the Constitution. Despite these accommodations, St. Augustine was quite careful to carry out the legal requirements of the Constitution and to establish and to use the required constitutional institutions and procedures. The Floridanos of St. Augustine felt themselves to be as profoundly Spanish as their Cuban counterparts to the south who were able to comply more exactly with the dictates of the Constitution and its procedures. Both cities and regions appear to have appropriated the Constitution deeply into their political structures. They both promulgated the Constitution several times and established constitutional institutions in light of the guiding provisions. Only recently have scholars recognized the extent of the second promulgation of the Constitution of Cádiz in St. Augustine in 1820 and of the third promulgation of the Constitution in Santiago de Cuba in 1836. This contribution will examine the effect of the decrees of the Cortes, the promulgation and implementation of the Constitution of Cádiz, and the varied responses to revocation and re-promulgation of the Constitution in both locations.