Vilaflor de Chasna

Long before Europeans arrived, the highland territory known as Chasna was part of the Guanche kingdom of Abona. The area sat at the edge of permanently settled land, used mainly as a pastoral corridor for moving livestock up to mountain pastures. Some scholars believe Chasna was developing into its own distinct territorial unit within Abona, and the Chasna ravine appears in early documents as the boundary between the kingdoms of Abona and Adeje.

The kingdom of Abona aligned itself with Spanish forces during the conquest — the mencey had confederated with the governor of Gran Canaria before 1490 — but after the conquest ended in 1496, the highlands of Chasna became a refuge for Guanche resisters. The distribution of land then began under new governor Alonso Fernández de Lugo. Initial colonisation centred on Porís de Abona from 1498, but within decades the focus of the area had shifted firmly to Chasna-Vilaflor.

In 1504, lands around the Chasna river were granted to conquistadors Jerónimo de Valdés, Andrés Suárez Gallinato, Guillén Castellano, and Fernando de Espinosa. Others who received land included the former mencey of Adeje, baptised Diego, and Nicolás Tello of the royal court. By 1508, those four original grantees had transferred their holdings to Sancho de Vargas, the island's chief magistrate, and it is these figures who are considered the founders of Vilaflor.

In 1533, Pedro Soler and his wife built a chapel dedicated to Saint Peter the Apostle. By 1568 it had been raised to a parish church, becoming the seat of the Benefice of Abona, which encompassed Vilaflor, Arona, Granadilla, San Miguel, and Arico. An Augustinian convent dedicated to Santa Catalina Mártir was founded in 1613, with its patronage later changed to San Juan Bautista in 1627 after Captain Juan García del Castillo built the convent chapel.

In 1602, Pedro Soler de Padilla — grandson of the town's founders — and his wife María de Cabrera established the Mayorazgo del Heredamiento de Chasna, a landholding that generated legal disputes for generations. That same year a court ruled against Soler de Padilla in a dispute with the town council and residents over cleared land, and in 1640 he was again in litigation with residents over his claim to levy tribute on their plots.

Vilaflor is also the birthplace of the first Canarian saint, a missionary who worked in Guatemala, and who remains a defining symbol of the town today.

The parish church of San Pedro Apóstol, declared a protected monument in 1985, holds a substantial collection of artistic works inside. Close by stands the Casa de los Soler, also known as the Marqués house, a well-preserved example of traditional Canarian architecture. The small hermitage of San Roque, to the southwest of town, dates from 1614.

Further out, a water mill in the Barranco del Cubo operated continuously from 1644 to 1915. The town as a whole preserves traditional rural architecture typical of southern Tenerife.