Cuba in 2-3 days
Unless you’re coming from Mexico or are on a tour of the Caribbean it seems a bit foolish to travel all the way to Cuba for a long weekend. However, if that’s the case then make straight for Havana. Spend a day mooching around Havana Vieja (the old town), another immersed in history at the Museo de la Revolucion and the Plaza de la Revolucion. On your final day, after a night out in Vedado take your hangover to a nearby beach like Playas del Este.
In 7-9 days
Choose between heading east or west after two days in Havana. Go west for lazy days spent sunbathing at the idyllic Cayo Levisa, exploring the tobacco plantations of Vinales and diving the vivid coral at Maria la Gorda. Head east for a Che Guevara pilgrimage to Santa Clara, the raucous nightlife and colonial treasures of Trinidad and finally a few days relaxing on the white sands at Varadero.
Two weeks +
Combine both of the above or get a flight from Havana to the sleepy coastal town of Baracoa or Cuba’s second city Santiago de Cuba and make your way back to the capital overland. Pass through laid-back Bayamo, historical Camaguey and the blissful islands of Cayo Coco and Cayo Guillermo before picking up the pace again in Trinidad.