CHILE CYCLING TOUR OVERVIEW

From Santiago’s sunlit plazas to Osorno’s snow-clad summit, this four-week odyssey through Chile is a journey across landscapes. We begin in the legendary wine valleys of Chile, where Jesuit missionaries planted the first vines and revolutionary spirits once rode. We follow the coast south to Pichilemu’s surf-pounded shores and Curanipe’s timeless fishing streets, before turning inland to cross the volcanic Andes into Patagonia — a land of smoking peaks, ancient forests, and wild beauty. Descending to the adventure capital of Pucón, we weave through the Lake District, ferry to the mythic islands of Chiloé, and return to circle Lago Llanquihue for the grand finale: the climb up Volcano Osorno, where the month’s epic ride gathers in one sweeping view. This is Chile at its most vivid — a country to be cycled, savoured, and remembered.

Conquistadors & Carmenère - Santiago, the city once founded by Pedro de Valdivia as the spearhead of Spain’s conquest of Mapuche lands, now a metropolis where glass towers and colonial churches face off like wary rivals. Southward, the route unwinds through the wine valleys of Casablanca, Maipú, and Colchagua — their ordered ranks of vines recalling not only the Jesuit missions who first cultivated them, but also the gaucho and peasant labourers whose hands have shaped the land. Here, the sun is generous, the soil rich, and the air perfumed with the promise of Carmenère and Cabernet! Che Guevara, in his youth, rode through these valleys on La Poderosa, a young medical student still yet to be transformed into the icon of rebellion; the same mountains and plains that framed his journey still roll past our wheels.

The Edge of the Continent - From the vinous heart of Chile, we turn west to meet the raw, salt-stung Pacific. The coast at Pichilemu, Chile’s surf capital, is less a beach resort than an elemental arena where ocean meets land in thundering dispute. Southwards to Curanipe, the coastline wears a wilder face — cliffs that might have served as perches for watchful Chono or Lafkenche fishermen to thrilling modern hotels set amongst the rugged beaches, rocks and dunes. This is a realm where nature insists on primacy; roads cling to the contours of headlands, sea fog curls inland, and every evening ends with a sunset fit to stir a conquistador’s painter.

Into Patagonia - From the sea, we pivot inland, cutting a diagonal towards Patagonia — a place that has always belonged as much to myth as to geography. Climbing through forests older than the Inca, we approach Lonquimay, its volcanic slopes crowned in snow, ringed by monkey puzzle trees that could be props from a Tolkien set. This volcanic wonderland shaped and fuelled the revolutionary thoughts of Ernesto ‘Che’ Guevara - he cuts a fascinating figure - equally revered and reviled around the world. Here we cross into Patagonia and the rest of the world feels very far away. The air is thinner, the silence deeper, the road a ribbon between mountains that smoulder quietly. Patagonia announces itself not with fanfare, but with the unshakable sense that here, nature has the final word.

Lakes, Legends & Lava - We descend to Pucón, where the perfect cone of Villarrica volcano looms over an adventure town alive with kayaks, mountaineers, and the scent of woodsmoke. From here, the Lake District unfolds: glacial waters still as mirrors, each framed by snowy peaks - it is magic cycling. A ferry carries us to Chiloé, where wooden churches rise like stranded ships and the sea’s myths are spoken as everyday truth: ghost ships, sea spirits, and ancient mariners who still shape the tide. It is a unique unforgettable place.

The Finale- Osorno's Summit - Back on the mainland, we circle Lago Llanquihue, its vast blue waters shimmering under the gaze of Osorno - the volcano whose snowcap gleams in the sun. To climb its slopes by bicycle is to confront both geology and legend — for in its symmetry there is something of the gods that the Mapuche feared and honoured. This final climb is a rite of passage — a long, elegant sweep of tarmac rising into the sky. At the summit, the view unfurls — lakes, volcanoes, and the green quilt of Chile stretching to the horizon. It’s the perfect finale to our epic odyssey!