Houseboating is mainly known as a popular recreational activity, that takes place all around the world, involving groups of people of all ages, aboard houseboats of all varieties and sizes. Houseboating is a relatively recent, but this practice seems to have a very ancient history. In fact, it can find its roots in India as well as in China or in the European continent, but the history of this practise has often been told indistinguishably with the origins of pleasure boating. It is hard to define which could have been the very first houseboat or floating home in history, since they have in common almost all the features that will distinguish it from working and military boats. This fact plus a diffused imprecise definition of ‘houseboat’, in the past as nowadays, makes it difficult to reconstruct the true beginning of houseboating, without mixing it with the birth of pleasure yachting. Even if houseboats and pleasure boats are often used as synonymous, these kinds of crafts have in common only the purpose of being both dedicated to a spend some leisure time on board. However if yachts main aim is to sail, with navigation as the main activity to do on board, houseboats primarily feature is to be used as a home, not necessarily moving around but simply floating. Knowing this difference, houseboats may be even older than pleasure boats, with the Thalamegos and the Nemi ships as its most famous ancestors. The aim of this work is to define the difference between houseboats, floating houses and pleasure boats, while tracing their forerunners in the Ancient History of the Western World. The most famous Hellenistic floating palace, the Talamegos, the Roman lusoriae and cubiculatae and the Nemi Ships have been analysed in this work in order to point out similarity and differences between houseboating and pleasure boating, showing links and features with the crafts of today.