Jeannine Williamson takes a luxurious Cuba cruise on an old-fashioned clipper to see the Caribbean island in style

Cuba Cruise

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 boxescycles 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.

In this instance, the ship was as atmospheric as the destination, and an integral part of the experience. Swedish entrepreneur and sailing enthusiast Mikael Krafft fulfilled a boyhood dream when he launched the Star Clippers line in 1991, recreating a modern version of the beautiful trading ships that ruled the waves in the 19th century.

I was aboard Star Flyer, the first in the fleet.

After a day in Havana, and the glamour of a guided tour in a bright pink 1950 Cadillac, the movie-scene feeling rolled on as we set sail for the first time.

With a chilled glass of champagne to hand, we stood on the teak deck to watch the 16 sails unfurling on four masts stretching up to 226ft.

Star Flyer is motorised but where possible it’s under sail, which was around 70% of the time on our 1,039 nautical mile Havana to Cienfuegos cruise, which also took in small Cuban islands in the Canarreos archipelago, plus Grand Cayman and Jamaica.

Climb the rigging

Carrying 170 passengers and 77 crew, the ship is relaxed and informal, and it was a surprise to find we could visit the bridge at any time and chat to the captain and officers, except when Star Flyer was navigating in and out of port.

In between stops, most passengers chose to relax on the sun deck, with its two small pools, or in the cosy brass and wood-trimmed library and lounge.

Entertainment is low-key, but the daily programme includes plenty to do, from an early-morning exercise class through to talks from the captain, water sports, quizzes,a singalong with the resident musician and, one of my favourites, a stargazing session.

If you’ve got a head for heights, don’t miss the chance to climb the rigging to the crow’s nest.

Egged on by the crowd that had assembled on deck, strapped into a safety harness and armed with the hint to look straight ahead rather than up or down, I reached the platform 100ft above the sea to be rewarded with some of the most unforgettable views of the whole trip.

Out and about

Excursions were on offer at every port, along with the option to take free tenders to small Cuban islands to walk or laze on the beach. One day, chefs and waiters came with us and set up a barbecue.

Another highlight was an included trip to the town of Trinidad, which built its wealth on the sugar industry. Again, it was like stepping back in time as we wandered past pastel-coloured buildings, old men playing dominoes in the street and the trademark classic cars.

Most nights we’d gather in the Tropical Bar, swapping tales of the day’s seafaring or land-based adventures. Unsurprisingly, there was never a shortage of things to talk about.

Getting there

Star Clippers offers a variety of seven- to 11-night Cuban cruises between Havana and Cienfuegos, with an overnight stay on board in one or both cities. A nine-night cruise is priced from £1,705, including all meals. Holidays including flights and transfers can also be arranged.

For further details and departure dates, call 0808 231 4798, or visit

Woman’s Weekly travel offer

Cuba, Central America & The Caribbean Cruise

47 days from £3,279pp

Departing 29 October 2017 – book before 31 May and save up to 40%.

Cross the Atlantic to discover the treasures of the Caribbean, Cuba, Costa Rica, Panama and Colombia.

To book, go online at or call 0330 160 7857 quoting code IWW