Cuba... Under Sail

For a holiday to remember, take a luxurious cruise on an old-fashioned clipper to see the Caribbean island in style.

- Jeanine Williamson

Stepping out of the cruise terminal, I feel as if I’ve walked straight on to a film set. A street vendor on a bike laden with wooden boxes cycles slowly past a crumbling colonial building, men in white fedora hats stroll along the waterfront deep in conversation and every other car seems to be a 1950s American classic or a battered old Soviet vehicle.

Welcome to Havana, an open-air museum jam-packed with Pontiacs, Oldsmobiles, Chevrolets and all manner of cars imported to the country before the late communist leader Fidel Castro took power in 1959 and most US imports were stopped. Although things are gradually starting to change, to outside eyes it remains an enthralling country and is completely different from anywhere else in the Caribbean.

On-board comfort

For all its charms, travelling around Cuba can be challenging. A shortage of good hotels makes accommodation hard to find, service can be hit and miss and even the best-laid plans are subject to the idiosyncrasies of local bureaucracy. This makes cruising a fantastic way to soak up Cuban colour and culture, coupled with plenty of creature comforts back in your floating home.