Walking holidays in Cuba

Since discovery by Christopher Columbus in 1492, Cuba has seen colonisers come and go, dictators overthrown, and some of the Cold War’s most dramatic events played out on its shores. Despite all this turmoil, Cuban life carries on to a soundtrack of swaying palms, traditional salsa music, and the satisfying clink of a glass or two of rum. 

A time capsule capital 

Once the hangout of American mobsters, literary legends, and stars like Frank Sinatra and Ava Gardner, Havana harks back to a bygone era. Like a huge open-air museum, Old Havana has been awarded UNESCO World Heritage status and tempts with classic 50s cars, Art Deco buildings, avant-garde street art, and lashings of faded grandeur. 

Our Cuba walking holidays include sightseeing at all the capital’s top spots, plus a free day to explore on your own. Drop by some of Ernest Hemingway’s favourite watering holes for a drink and see where the legendary American author wrote classic novels, For Whom the Bell Tolls and The Old Man and the Sea with a visit to Finca Vigia – his former home turned museum. 

And while daytime in Havana puts sightseeing centre stage, come evening it’s all about indulging in rum cocktails and mixing with the locals as they dance to rocking Cuban rhythms. 

Explore beyond the beach 

Though it’s the Cuban capital that gets all the love, this paradise isle has plenty of places that are equally attention worthy. Take a trip to Trinidad where lofty colonial mansions of sugar barons stand perfectly preserved and stop by Santa Clara to see the mausoleum of Cuba’s iconic black bereted revolutionary hero, Che Guevara. 

Out in the countryside, Viñales steals the spotlight. This rural stunner is all steep-sided limestone hills (known as mogotes), sun-browned tobacco fields, and cigar-chomping farmers who use oxen carts over classic cars. Expect sunrise hikes in the hills, cigar rolling demonstrations, and meals made with fresh organic produce. 

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