This study presents a systematic evaluation of the homogeneity of daily surface temperature observations for the Caribbean and neighboring regions on a monthly timescale. The reference series are developed using adjacent sea-surface temperatures (SSTs). This novel approach is undertaken instead of the conventional use of highly correlated nearby stations, given the sparse station network for the Caribbean and adjacent Caribbean. The temperature data are from the regional climate change workshops held for the Caribbean, and Central and Northern South America in 2001 and 2004, respectively, complemented with data from the National Climatic Data Center (NCDC), the Caribbean Institute for Meteorology and Hydrology (CIMH), and the Caribbean meteorological stations. Correlations are used to explore the degree of association between the maximum and minimum temperatures and SSTs, and homogeneity tests are performed on their individual and difference series (e.g., maximum temperature minus SSTs). The results suggest SSTs as a viable option for use in evaluating homogeneity in the data sparse region of the Caribbean. Common statistically significant change points identified across at least three stations are investigated using composite analysis to determine links to large-scale atmospheric circulation patterns. The study identifies two homogeneous periods from the analyses, i.e., 1970–1992 and 1984–1998, with the former used to reanalyze some extreme temperature trends for the Caribbean and adjacent Caribbean. The results are found to be consistent with those obtained from the 2001 Caribbean data workshop.