The city of Taranto, in the south-east of Italy, is experiencing a transition from one of the most polluted and industrialized area characterized by the presence of the largest integrated steelworks in Europe, to a center of attractions of investments in innovation on sustainability and tourism. Among sustainability projects, urban wind energy is emerging as a technology useful in diffusion of smart grids for energetic sustainable development and also an interesting growing niche market in which there could be new investment opportunities. Numerous projects aimed at developing wind energy production are under constructions and wind characteristics and power potential of various sites have been studied in many Mediterranean countries. The urban wind analysis may represent a new tool to complete local wind atlases including the built environment, to evaluate changes that weathering may cause in the physical and architectural state of buildings, and to analyze the dispersion of pollutants from sources to receptor sites. In this paper, an analysis of wind potential and characteristics in Taranto, Apulia, a north Jonian urban site in Italy, has been performed by using high time resolved (10 min) meteorological data collected over a time span of two years, in the aim to describe the numerical procedures adopted to perform fitting of wind speed data without using special software. This urban site, in the first year of investigation from May 1st, 2009 to April 30th, 2010, was subjected to main wind regimes that come mostly from N with 12.27% and SSW with 9.89% of total hours; the calm occurred with a frequency of 10.94%. In the second year, from May 1st, 2010 to April 30th, 2011, the winds also blown predominantly from N with 12.56% of the total annual hours, and SSW with 9.33%, while the calms reached 11.08%. Dispersion of pollutants emitted from various sources among cement factory, a quarry/landfill, a refinery and the steelworks, poses serious health risks to population mainly resident downwind the prevalent wind directions. Simply computed mean wind speeds had values of 1.84 (sd = 0.26 m/s) in the first year and 1.90 m/s (sd = 0.30 m/s) in the second year under investigation. Weibull’s k values, measuring the wind potential of the site, were higher during the spring-summer warmest months and lower during the autumn-winter; the lowest appeared in November 2009 (0.639) the highest in June 2010 (1.665). Mean yearly values of k were 1.210 (sd = 0.18) in the first year and 1.065 (sd = 0.24) in the second year of the study, the correlation between the monthly values of k in the years under consideration was R2 = 0.59 (p = 0.043) indicating that although variations occurred, the wind potential remain partly unaltered from one year to the other examined. LCOE (Levelized Cost of Electricity) for the wind turbines chosen among the 35 ones listed in the “Catalogue of European Urban Wind Turbine Manufactures”, excluding those with rated power below 0.1 kW, ranged from 0.12 to 10.6 €/kWh and differs slightly in the two years examined. The values were competitive with some off-shore and on-shore installations, biogas and photovoltaic, but it does not consider pollution costs and subsidies. The proposed solution was economically viable, also by considering the possible integration in a hybrid photovoltaic-wind system, or fossil-based heat generator system supplemented by solar photovoltaic and wind energy.