The Caribbean is a complex region that heavily relies on its seasonal rainfall cycle for its economic and societal needs. This makes the Caribbean especially susceptible to hydro-meteorological disasters (e.g., droughts and floods), and other weather/climate risks. Therefore, effectively predicting the Caribbean rainfall cycle is valuable for the region. The efficacy of predicting the Caribbean rainfall cycle is largely dependent on effectively characterizing the climate dynamics of the region. However, the dynamical processes and climate drivers that shape the seasonal cycle are not fully understood, as previous observational studies show inconsistent findings as to what mechanisms influence the mean state and variability of the cycle. These inconsistencies can be attributed to the limitations previous studies have when investigating the Caribbean rainfall cycle, such as using monthly or longer resolutions in the data or analysis that often mask the seasonal transitions and regional differences of rainfall, and investigating the Caribbean under a basin-wide lens rather than a sub-regional lens. This inhibits the ability to accurately calculate and predict subseasonal-to-seasonal (S2S) rainfall characteristics in the region. To address these limitations and inconsistencies, the research in this thesis examines the seasonal climatology, variability, and characteristics of the Caribbean rainfall cycle under a sub-regional and temporally fine lens in order to investigate the prediction of the cycle. Regional variations and dynamical processes of the Caribbean annual rainfall cycle are assessed using (1) a principal component analysis across Caribbean stations using daily observed precipitation data; and, (2) a moisture budget analysis. The results show that the seasonal cycle of rainfall in the Caribbean hinges on three main facilitators of moisture convergence: the Atlantic Intertropical Convergence Zone (ITCZ), the Eastern Pacific ITCZ, and the North Atlantic Subtropical High (NASH). A warm body of sea-surface temperatures (SSTs) in the Caribbean basin known as the Atlantic Warm Pool (AWP) and a low-level jet centered at 925hPa over the Caribbean Sea known as the Caribbean Low-Level Jet (CLLJ) modify the extent of moisture provided by these main facilitators. The interactions of these dynamical processes are responsible for shaping the seasonal components of the annual rainfall cycle: The Winter Dry Season (WDS; mid-November to April); the Early-Rainy Season (ERS; mid-April to mid-June); an intermittent relatively dry period known as the mid-summer drought, (MSD; mid-June to late August), and the Late-Rainy Season (LRS; late August to late November). Five geographical sub-regions are identified in the Caribbean Islands, each with its unique set of dynamical processes, and consequently, its unique pattern of rainfall distribution throughout the rainy season: Northwestern Caribbean, the Western Caribbean, the Central Caribbean, the Central and Southern Lesser Antilles, and Trinidad and Tobago and Guianas. Convergence by sub-monthly transients contributes little to Caribbean rainfall. The wettest and driest Caribbean ERS and LRS years’ are then explored by conducting the following: (1) a spatial composite of rainfall using the daily rainfall data; and, (2) spatial composites of SSTs, sea-level pressure (SLP), and mean flow moisture convergence and transports using monthly data. The ERS and LRS are impacted in distinctly different ways by two different, and largely independent, large-scale phenomena, external to the region: a SLP dipole mode of variability in the North Atlantic known as the North Atlantic Oscillation (NAO), and the El Nino Southern Oscillation (ENSO). Dry ERS years are associated with a persistent dipole of cold and warm SSTs over the Caribbean Sea and Gulf of Mexico, respectively, that are caused by a preceding positive NAO state. This setting involves a wind-evaporation-SST (WES) feedback expressed in enhanced trade winds and consequently, moisture transport divergence over all of the Caribbean, except in portions of the Northwestern Caribbean in May. A contribution from the preceding winter cold ENSO event is also discernible during dry ERS years. Dry LRS years are due to the summertime onset of an El Niño event, developing an inter-basin SLP pattern that moves moisture out of the Caribbean, except in portions of the Northwestern Caribbean in November. Both large-scale climate drivers would have the opposite effect during their opposite phases leading to wet years in both seasons. Existing methodologies that calculate S2S rainfall characteristics were not found to be suitable for a region like the Caribbean, given its complex rainfall pattern; therefore, a novel and comprehensive method is devised and utilized to calculate onset, demise, and MSD characteristics in the Caribbean. When applying the method to calculate S2S characteristics in the Caribbean, meteorological onsets and demises, which are calculated via each year’s ERS and LRS mean thresholds, effectively characterize the seasonal evolution of mean onsets and demises in the Caribbean. The year-to-year variability of MSD characteristics, and onsets and demises that are calculated by climatological ERS and LRS mean thresholds resemble the variability of seasonal rainfall totals in the Caribbean and are statistically significantly correlated with the identified dynamical processes that impact each seasonal component of the rainfall cycle. Finally, the seasonal prediction of the Caribbean rainfall cycle is assessed using the identified variables that could provide predictive skill of S2S rainfall characteristics in the region. Canonical correlation analysis is used to predict seasonal rainfall characteristics of station-averaged sub-regional frequency and intensity of the ERS and LRS wet days, and magnitude of the MSD. Predictor fields are based on observations from the ERA-Interim reanalysis and GCM output from the North America Multi-Model Ensemble (NMME). Spearman Correlation and Relative Operating Characteristics are applied to assess the forecast skill. The use of SLP, 850-hPa zonal winds (u850), vertically integrated zonal (UQ), and meridional (VQ) moisture fluxes show comparable, if not better, forecast skill than SSTs, which is the most common predictor field for regional statistical prediction. Generally, the highest ERS predictive skill is found for the frequency of wet days, and the highest LRS predictive skill is found for the intensity of wet days. Rainfall characteristics in the Central and Eastern Caribbean have statistically significant predictive skill. Forecast skill of rainfall characteristics in the Northwestern and Western Caribbean are lower and less consistent. The sub-regional differences and consistently significant skill across lead times up to at least two months can be attributed to persistent SST/SLP anomalies during the ERS that resemble the North Atlantic Oscillation pattern, and the summer-time onset of the El Niño-Southern Oscillation during the LRS. The spatial pattern of anomalies during the MSD bears resemblance to both the ERS and LRS spatial patterns. The findings from this thesis provide a more comprehensive and complete understanding of the climate dynamics, variability, and annual mean state of the Caribbean rainfall cycle. These results have important implications for prediction, decision-making, modeling capabilities, understanding the genesis of hydro-meteorological disasters, investigating rainfall under other modes of variability, and Caribbean impact studies regarding weather risks and future climate.