A brief history of the serenade
Venice, throughout its history, has been associated with romance and artistic expression. Serenades, a tradition of expressing love and devotion through music, naturally fit into this cultural identity.
Beyond their primary role as navigators, gondoliers often supplemented their income by offering singing and musical entertainment to passengers. Some even formed informal singing groups, further solidifying the connection between gondolas and music.
Centuries ago, they also used song as a means to lure prospective customers. Many gondoliers also acted as intermediaries between lovers, using their serenades as metaphors to set the mood between couples (back in the day, gondolas also came equipped with a felze, or covering, which shielded its passengers from prying eyes).
Nowadays, not all gondoliers sing, and some even consider it insulting if you request them for a song. So, it's best to speak with gondoliers beforehand to know who will accommodate your needs.