This paper considers the structure of the regional energy supply of Crimea and presents the characteristics of the main groups of regional electricity producers, including combined heat and power plants, mobile gas turbine power plants, renewable energy sources, and backup power sources. It is proposed, depending on the purpose of calculations in the context of the transportation problem under consideration, to use average actual rates for a given period with energy suppliers as tariffs (the calculation purpose is to reduce the electricity production and transportation cost), as well as conditional qualitative assessments, such as “fines” (the purpose is to improve the environmental friendliness and reliability of the system as a whole). The influence of the produced solar plant power on the operating modes of the Crimean energy system is assessed. The solar power production optimization technique that affects the reliability and quality of power supply is developed. Various energy supply scenarios for Crimea are generated, including peak and average power consumption modes with various options for solar activity, season, including and excluding energy sources under construction, and off-season repair of power sources. Based on the calculation data, the reliability of the regional energy system is estimated for various power supply scenarios, as well as the need to use an energy bridge for a power exchange with the mainland.