For such a seemingly laid-back city Valladolid has quite a fiery history. Initially established in 1543, next to the lagoon of Chouac Ha and named after the then capital of Spain, the city was moved to its current location due complaints by the settling Spaniards about the amount of mosquitoes in the area.

Its relocation resulted in the destruction on the Maya town of Zaci and the Spaniards reused the stones to build present-day Valladolid. The displaced Maya attempted to revolt but were crushed by troops that were called in from Merida.

Maya discontent may have been extinguished at the time but it stirred under the surface. Almost 300 years later, the native Mayans rioted once again against the Spanish, killing and looting and in 1848 the city was ignited by the War of the Castes that spread through the Yucatan. Latinos were forced to abandon Valladolid, although they would return again once the city was retaken later in the war.

Nowadays Valladolid is a tranquil city, nicknamed the Sultan of the East due to its stunning colonial and Moorish-style architecture.

In 1910 the city played a role in the Mexican Revolution, with the Dzelkoop Plan, which called the people to rise up against the government, being signed there.