The exploitation of wind energy is rapidly evolving and is manifested in the ever-expanding global network of offshore wind energy farms. For the Small Island Developing States of the Caribbean Sea (CS), harnessing this mature technology is an important first step in the transition away from fossil fuels. This paper uses buoy and satellite observations of surface wind speed in the CS to estimate wind energy resources over the 2009–201911-year period and initiates hour-ahead forecast-ing using the long short-term memory (LSTM) network. Observations of wind power density (WPD) at the 100-m height showed a mean of approximately 1000 W/m2 in the Colombia Basin, though this value decreases radially to 600–800 W/m2 in the central CS to a minimum of approximately 250 W/m2 at its borders in the Venezuela Basin. The Caribbean Low-Level Jet (CLLJ) is also responsible for the waxing and waning of surface wind speed and as such, resource stability, though stable as estimated through monthly and seasonal coefficients of variation, is naturally governed by CLLJ activity. Using a commercially available offshore wind turbine, wind energy generation at four locations in the CS is estimated. Electricity production is greatest and most stable in the central CS than at either its eastern or western borders. Wind speed forecasts are also found to be more accurate at this location, and though technology currently restricts offshore wind turbines to shallow water, outward migration to and colonization of deeper water is an attractive option for energy exploitation.