In 2001, dengue transmission was detected in Havana City where 12,889 cases, mostly of DENV-3 type, were reported with 78 DHF cases and 3 deaths due to Dengue. A simple mathematical model, the Richards model, is utilized to investigate the temporal progression of the epidemic in 14 municipalities in Havana City and to quantify the transmissibility of the epidemic via the basic reproduction number R0. Model fits using weekly reported dengue case data for each of the municipalities as well as for all of Havana City indicate either a 2-wave or 3-wave outbreak. Estimates for R0 vary from 1.97, 95% CI: (1.94, 2.01), for Arroyo Naranjo to 61.06 (60.44, 61.68) for Boyeros. Wide regional variability in our estimates of R0 for dengue is consistent with reported values in literature from various regions of the world, most likely due to heterogeneity in community structure, community-wide pre-immunity, geographical locations, and social networking. By case reporting week, the dengue epidemic in Havana had started to go down initially around weeks 20-22 (first turning point/peak incidence). However, infections spread once again after week 24, perhaps due to Hurricane Michelle, one of the most destructive and wettest tropical cyclones ever in Cuba that may have contributed to a protracted and more severe epidemic. For all municipalities with 3-wave, model fit indicates a new third wave occurred after Christmas/New Year in weeks 31-32, likely attributable to a decrease in reporting due to reluctance for hospital visits during the holidays. Our result illustrates the potential impact of climatological events on disease spread. It further highlights the need to be well-prepared for possible worsening disease spread in the aftermath of natural disasters such as hurricanes/typhoons.