Though the Havanese is a relatively new breed in America, it has quite a long history outside the US. It is the national dog of Cuba and this country's only native breed; indeed, it was developed solely in Cuba. The origins of the breed's ancestors are unknown; some say that Spanish sailors brought a dog over from either Spain or Tenerife (one of the Canary Islands), while others claim that Italian traders would often give Bolognese-type dogs as gifts to wealthy Cuban aristocrats to gain their favor and business. It is almost certain that merchants would give Bichon-like dogs to aristocratic Cuban women to try to establish trade connections with the important Cuban families. Whatever its history, it is obvious that the Havanese enjoyed life as an aristocratic canine and even traveled back to Europe to fulfill the role of court companion.

By the 18th century, Cuba had actually become one of the most important centers of culture and elegance in the New World, attracting much of the European aristocracy, especially for vacation purposes. When they returned to their countries, they would bring the Havanese, which eventually became popular in the royal courts of Spain, England and France. In Cuba, the old aristocracy was disappearing and was being replaced by the budding bourgeoisie, who enthusiastically embraced the presence of the Cuban canine. The Havanese became a watchdog, children's playmate and herded the poultry flock of his upper class owners. These dogs lived their entire lives in the rooms and courtyards of wealthy mansions and were rarely, if ever, seen in streets or public places; if they needed to accompany their upper class families, they were taken along in carriages and coaches.

It became very trendy to own one of these dogs, though breeding for personal or commercial purposes was virtually non-existent. Instead, Havanese were bred to be given as gifts and signalled both the wealth of the giver and the importance of the relationship with the party who was being given the dog. They were often given in compensation for a very valuable service rendered. When the Cuban revolution set in, the upper class began to flee Cuba out of fear of being executed. Since the Havanese was seen as a symbol of both Cuban aristocracy and the subsequent wealthy bourgeoisie, it was targeted by the revolutionaries and only a small handful of Cubans who fled the country were able to actually take their Havanese with them. Some sources claim that only three families were able to leave Cuba with their Havenese with them during the years spanning 1950 and 1960. It seems like among these three families, 11 dogs actually made it out, and most of the existing Havanese today, outside of Cuba, have been bred from the gene pool of those 11 dogs, with concerted breeding efforts starting around the 1970s.