Photo: Adam Jones from Kelowna, BC, Canada · CC BY-SA 2.0
Cuba · Cuba
Cycling Cuba works because the traffic never came back. The classic line runs west from Havana's crumbling Malecón to Viñales, where limestone mogotes rise out of red-earth tobacco farms, then east through the Zapata wetlands and the Bay of Pigs to Trinidad's cobbled UNESCO core, finishing among the son and trova bars of the southeast. Casa particular hosts feed you lobster dinners and strong coffee, and conversations at every stop reach places tour buses never do. The thing that catches cyclists out is scarcity. There are no bike shops worth the name outside Havana, so bring every spare — tyres, tubes, spokes, chain links — plus cash, because cards fail and rural ATMs barely exist. Ride at dawn to beat the Caribbean heat, and treat pothole shadows with suspicion. November to March is the dry-season sweet spot. Around £900 covers a week of casas, meals and transfers once you have landed; a support vehicle roughly doubles it but rescues the headwind days.
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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