Cuba conjures up images of classic cars, mojitos and salsa music, but for so long, the island – the largest in the Carribbean – has been somewhat of a question mark for travellers. For decades, it was a mystery. Tourism all but stopped after the revolution in 1959, only to start again in the early 90s, after the collapse of the Soviet Union.
It was only eight years ago, that President Obama lifted the travel ban for Americans, marking a new era for tourism on the island. Today, the country still raises eyebrows. ‘Is Cuba safe?’, my friends asked as I detailed my planned adventure across the country for two weeks.
‘I’m sure it’ll be fine,’ I had hastily replied. Talk about an understatement. I was so captivated by the place that I intentionally missed my flight back to London, and stayed an extra week in paradise.
And don’t just take my word for it: Cuba has just been named by Condé Nast Traveller in their list of the best 25 places to go in 2025 with the publication citing its ‘UNESCO-protected cities, gelato-colored classic cars — and its loquacious, quick-witted locals’ as reasons to visit.’ I began my journey in Havana, touching down in the capital in late February 2024. I had signed up for a group trip experience with WeRoad, who had planned five stops on our itinerary including villages and cities that would showcase all that Cuba had to offer.
So, if you’re planning a road trip with a difference, here’s how to spend three weeks in Cuba. W.