In the authors’ previous report, a new piezoelectric cylindrical shell wind power generation flag had been proposed as a flexible and durable power generation structure that utilizes vortex excitation vibrations. Preliminary experiments showed that it was expected to generate more than 10 times more power than the conventional planar-shaped wind power generation flag. In the present flag, the cylindrical Bluff Body, which excites vortices, also plays the role of a vibrating structure, and the wind speed region where these vibrations are excited is greatly affected by the boundary conditions corresponded to the different supporting methods. However, the authors have previously reported on the relationship between vibration and wind speed during power generation with the cylindrical shell which was assumed to be freely supported. In this study, the relationship between the wind speed range, the excited vibration mode, and the amount of power generated by the different boundary conditions are investigated experimentally. It was implied from the experimental results that superior supporting condition of the present cylindrical shell energy harvester for wind power generation characteristics will depend on the radius of the cylinder. Further study will be needed to establish the design method of the proposed wind energy harvesting method.