Origin and evolution of the gondola have been reconstructed from historical and documentary written and pictorial sources (figures in books, engravings and paintings), in relation to the physical environment of the Lagoon, its morpho-dynamics with shallow and deep waters, marshes and canals. Particular care has been applied to the physical and hydrodynamic aspects in order to interpret the data and understand how the ancient Venetians could have had an advanced knowledge of the tidal range from sea stairs, tidal phase from the algae colour and direction, bottom depth from surface ripples, and exchanges between the Lagoon and the sea from suspended debris. The various elements of the boat are considered in terms of use and physical advantage, e.g. rowing style, cabin, hull and decorations. The boat evolution has been followed and documented over the centuries. This study clarifies the original shape of the gondola in the 11th century, from the analysis of the contemporary manuscripts and Byzantine mosaics in Ravenna and Venice, and a tablet of the early 14th century. In the 16th century, the gondola changed shape and size. The reason of this restyling was unknown, but has been found in the contemporary edicts, diaries and chronicles and other historical sources. The transformation was kept as a military secret, as well the production of a fleet of small boats provided of rostrums to sail on the rivers Po and Adige and fight against Ferrara and its Allies of the League of Cambrai. A comparison with the Viking- Norman vessels of Bayeux, Palermo and some codices show several strong analogies with the military gondolas of the 16th century. An overview of the written and pictorial sources has allowed to classify the various gondola types and recognize several technical details. Finally, the size and depth have been considered to interpret the ancient chronicles that mentioned that in the occasion of the most extreme storm surges, the gondolas could ride on San Marco Square, i.e. the flooding water depth necessary to float and to navigate over street paving.