Photo: Yomangani · Public domain
Havana · Cuba
Cycling Cuba from Havana to Santiago de Cuba along the Carretera Central runs the length of the island: the sugar country east of Matanzas, the colonial cores of Trinidad and Camagüey — Trinidad's Valle de los Ingenios still holding its ruined mills and the Manaca Iznaga bell tower — and the musical heartland of Santiago, where son cubano developed. The 1,100-kilometre route crosses the island's mountainous spine beside the Sierra Maestra, where Fidel Castro's guerrilla campaign began. The tobacco country of the Viñales Valley is worth a loop of its own, but it lies in Pinar del Río, west of Havana and in the opposite direction from this ride — add it before you turn east rather than expecting to pass through it. The combination of extraordinary music, Caribbean cuisine and 1950s American car culture is unlike anywhere else on Earth.
Prefilled for 1 November 2026 — the next best-season window. Search on partner sites — opens in a new tab.
Tour operators & guided experiences via Viator
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