Long before the Castilian conquest, the highlands now occupied by Vilaflor de Chasna formed part of the menceyato of Abona, one of the nine Guanche kingdoms into which Tenerife was divided. The word "Chasna", of aboriginal origin, gives its name to this whole southern district of the island and has been interpreted as "step" or "terrace", in reference to the stepped relief that rises from the coast towards the summit. For the ancient Canarians, the pine forests and mid-altitude lands of Chasna were a place of grazing and seasonal transhumance, where livestock found fresh pasture in summer; that pastoral vocation would shape the character of the place for centuries.

After the island was incorporated into the Crown of Castile at the end of the 15th century, the area was gradually settled thanks to livestock, the timber of its pine forests and, above all, the water of its springs, a scarce and precious resource in the south. Tradition attributes the founding of the village to the Catalan settler Pedro Soler and his wife Juana de Padilla, daughter of the owner of the lands of Chasna, Juan Martín de Padilla, who around 1533 built a hermitage dedicated to Saint Peter the Apostle. That temple, raised to parish status in 1568, became the heart of the hamlet and the seed of today's historic centre, with its cobbled streets and traditional Canarian architecture.

Vilaflor holds one of its most famous titles thanks to its location: with its town centre lying at around 1,400 metres above sea level, it is considered one of the highest inhabited towns or settlements in Spain and the highest in the Canary Islands. The fact deserves a precise note: by total surface area there are municipalities whose territory reaches greater heights —on this very island, La Orotava encompasses the summit of Teide— but no consolidated urban centre in the islands sits as high as that of Vilaflor, earning it the reputation of "the highest town in the Canary Islands". This altitude shapes its climate, its landscape and its way of life.

On 21 March 1626, the most universal historical figure of the municipality was born in Vilaflor: Pedro de San José Betancur, known as the Holy Brother Pedro (Santo Hermano Pedro). A shepherd in his youth across these mountains, he emigrated to Guatemala, where he devoted his life to the sick, the poor and education, founded the first convalescent hospital and the first popular school in Spanish America, and created around 1656 the Order of the Brothers of Our Lady of Bethlehem (the Bethlemites). He died in Santiago de los Caballeros in 1667; he was beatified in 1980 and canonised by Pope John Paul II in 2002, becoming the first Canarian saint and the first Central American saint. His devotion still links Tenerife and Guatemala today.

Vilaflor's identity is inseparable from its natural surroundings. The municipality opens onto the Corona Forestal Natural Park, the most extensive protected area in the Canary Islands, home to one of the finest Canary pine forests (Pinus canariensis) on the island. There stands the famous Pino Gordo, a monumental specimen about 45 metres tall and nearly 9 metres in girth, several centuries old, a symbol of the town to the point of appearing on its coat of arms. Nearby lies the so-called Lunar Landscape of Los Escurriales, a cluster of chimneys and needles of white volcanic tuff sculpted by erosion, almost extraterrestrial in appearance.

Today Vilaflor de Chasna —its official name recovered in 2014 by adding its ancient Guanche toponym— is an essentially rural town of around 1,900 inhabitants that has turned its hallmarks into an economic engine. The Fuentealta natural mineral water, bottled in the municipality since 1975 from a spring in the highlands, and the high-altitude wine protected by the Abona Designation of Origin —with some of the highest vineyards in Europe— are its emblematic products. To these are added traditional agriculture, the craft of "rosetas" (Canarian openwork lace), and a tourism based on nature, hiking and pilgrimage that finds here silence, pine forests, clear skies for stargazing, and the living trace of a saint.