Towards the end of the 16th century, after the Castillo de la Real Fuerza was built, the Plaza de Iglesia became a military place where the soldiers of the Royal Force were making their military exercises. It received the name Plaza de Armas and day by day it lost its public character. This development impelled the city council to look for other areas that would be used for commercial and social activities. Thus, in 1587, nearly 30 years after the new square was initially proposed, the city council decided to recover the same place, destined to the new plaza. Consequently, the Plaza Nueva (New Square) emerged as an alternative to the Plaza de Armas at the end of 16th century. It was the first planned attempt in terms of the urbanism in Havana that arrived with some transformations from the 16th century until our days. Even though the city council made it desirable to buy a lot in the plaza by reducing the price considerably, the neighbors of the square were not very interested, as the place was like a big lagoon, still in 1610s. The drainage system of the square was improved in 1618 and 1620, as the area was suffering floods in rainy days due to the calcareous mantle of the soil that was making the drainage of the rain water difficult. About one century had to pass, so that the plaza could identify itself.

Towards the last third of the 17th century the Plaza Nueva flourished almost spontaneously by becoming the residential area of Havana’s wealthy citizens. It became the site of processions, bullfights and fiestas where these rich Creoles looked on from their balconies; however, it was also a site of executions. The plaza was used for different purposes, as residential, commercial and recreational area, without housing any religious, administrative or military building.

The square became a field where the Creole domestic architecture was experimented in the 17th and 18th centuries. The residencies with wooden balconies, roofs covered with tiles, and portals with columns topped with arches were prevailed in the square.

In the 18th century the Plaza Vieja turned into a popular open-air food market and the citizens commenced to call it Plaza del Mercado (Market Square). At that time the place was the commercial hub of Havana. With the birth of a new market in Plaza del Cristo in 1640, the name of the Plaza del Mercado was replaced by the name of Plaza Vieja (Old Square) in 1814 to differentiate it from the Mercado Nuevo (New Market) in Plaza del Cristo. Until today the square has also been identified by other names, such as Plaza Real, Mayor, Mercado, Fernando VII, the Constitution, Parque Juan Bruno Zayas and Parque Julián Grimau.

In 1908 the old market of the plaza was demolished to make room for a park. In 1952 the area of the park was transformed into an underground car parking that spoilt the view of the plaza considerably. Soon many of the buildings around the plaza slowly continued to deteriorate. Fortunately, when Old Havana was listed by UNESCO as a Cultural Heritage site in 1982, the restoration was initiated in the plaza. In 1996 the monstrous car parking was demolished to make way for the massive renovation project. The restoration, started in 1982, is gradually re-establishing the Plaza Vieja’s original atmosphere.

The plaza is surrounded by valuable colonial buildings from the 17th to 19th centuries that maintain stylistic unity, just as they are two-storey buildings that open to the outside through portals and galleries. There are also a few very striking early 20th-century art nouveau buildings.

The fountain at the center of the square is made of white Carrera marble. It is the replica of the original fountain surrounded by four dolphins from the 18th century that was the work of the Italian sculpture Giorgio Massari. It had been destroyed during the construction of the car parking.

On the southeast corner of the square, there is a bronze sculpture of a naked woman riding a rooster.  She is holding a large fork and wearing high heels. This unusual sculpture is the work of Roberto Fabelo, and it was installed in 2012.

On the northeast corner of the square, there is a modern sculpture made of iron that represents the bullfighting fan. It is the work of the Spanish Kieff Antonio Grediaga.

The Plaza Vieja (Old Square) is the second oldest square of Havana, after the Plaza de Armas, bordered by the Mercaderes, San Ignacio, Teniente Rey and the Muralla streets.

In the 16th century the Franciscan friars were complaining of the noisy activity of the vendors and the town criers in front of their humble church, as it was hindering the celebration of masses in their convent. The area in front of the convent, where later the Basílica Menor de San Francisco de Asís would be built, was the crossing point of the commercial activity due its proximity to the harbor. The Franciscan friars requested from the city council the creation of another plaza for commercial purpose.

On the other hand, due to the urban and commercial development of Havana in the 16th century, the city had to expand. In 1559 the city council decreed the establishment of another square about one hundred meters far from the convent, destined to the market and public celebrations, substituting the Plaza de Iglesia that had lost some of its space, when the construction of the Castillo de la Real Fuerza (Castle of Royal Force) had been initiated in the previous year. Even though the chosen area was completed as a new square, it remained to be in little demand for more than two decades, so that the city council decided to divide the area into plots and rent them, before the number of the residents would increase.