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Caribbean Cruising – The Dreamiest Ports of Call in Cuba

4th August 2017

Sugar-white beaches more beautiful than the mind can conjure; rolling hills dotted with tobacco fields where Cuban cigars are still rolled by hand; classic 1950s cars rolling down streets lined with charming Spanish-colonial architecture. Cuba is a captivating holiday spot to say the least.

It’s charismatic, mystifying and exotically beautiful all at once, and while it satisfies a most niggling sense of curiosity it has this funny way of leaving you feeling slightly perplexed, always craving more.

A Cuban cruise offers the perfect introduction.

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Musician in Old Havana, Cuba.
Music is everywhere in the streets of Old Havana.

It’s an easy, breezy way to get around and step ashore at various ports of call for a taste of the intriguing local history, culture and sights, with ample sunshine-filled hours to soak up those famed stretches of powdery sands and impeccably azure waters.

A Caribbean cruise to Cuba really is as good as it’s cracked up to be – the perfect mix of palm-tree-infused downtime and novel discoveries.

Our pick? Star Clippers – for their traditional fleet of graceful, four-masted tall sailing ships and the fact that they stop at stunning ports often untouched by the larger cruise ship crowd. Here’s a glimpse at some of the dreamiest ports of call in Cuba.


It’s an essential stop on every Cuban travel itinerary. The legendary, often-fantasised-about capital of Havana offers unmatched insight into Cuba’s story, its people and mentality and the character-drenched setting proves unforgettable.

Expect a kaleidoscope of colourful sights to marvel at: beautiful Cuban Baroque buildings, historic forts, interesting museums, renowned restaurants, lively public squares, and the mesmerising cobbled streets of Old Havana, which flaunt the UNESCO World Heritage tick of approval.

Specifically, a trip to the Museo de la Revolucion, Plaza de la Revolucion, Museo Nacional de Bellas Artes, the Morro Castle fortress and a cabaret show at Tropicana top the list of things to do and see.


Mural in Havana, Cuba.
Cuba is full of fascinating discoveries.

So much about Havana though is simply the experience you’ll have meandering the streets. Soak up the atmosphere, turn down a few random corners and see what you find – and don’t be surprised to stumble across locals dancing in the streets many times over and hear Salsa music streaming out of open windows.

Havana serves avid people-watchers well.

Equally fascinating is Havana’s evocative Malecon, especially if you’re rolling along the tarmac in a ‘55 Buick, Chevrolet Bel Air or some other 1950s-era gem of a ride. This seven-kilometre long seaside boulevard is one of the city’s most soulful thoroughfares and the cherished backbone of Havana’s social scene – where musicians, artists, fishers, friends and lovers alike congregate at any time of day or night.

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Classic car in Havana.
Enjoying classic ride through the streets is a must in Havana.

Roll along this stretch on your way from Havana’s Old Town to the more modern, less-touristy area of Vedado for a glimpse at the contrast.

And for the Ernest Hemingway fans, be sure to wind down to the tune of a daiquiri at La Floridita – the “world’s best” as proclaimed by the man himself – or else an iconic Cuba Libre (which translates as ‘Free Cuba’) at La Bodeguita del Medio – another one of his favourite watering holes.  

Punta Frances

It’s a little-visited corner of Cuba, immersed in tales of pirates, treason and gold. So much so that the area around Punta Frances, on Isla de la Juventud (‘Isle of Youth’), has been coined Cuba’s ‘Pirate Coast’.

The story goes that a French pirate named Latrobe buried stolen treasure on one of the island’s beaches after he attacked and captured two Spanish galleons laden with gold and jewels – then he himself was captured by the US military. The treasure has never been found (not that there haven’t been numerous attempts).

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Beautiful Cuban beach.
White sands meet pure waters at Cuba's stunning beaches.

Now the island is commonly called ‘Treasure Island’ and indeed, the classic namesake novel by Robert Louis Stevenson was written here in the flesh.

As a cruiser passing through, chances are the only treasure you’ll find is the natural kind.

Punta Frances is an adored launching pad for scuba diving in Cuba; Punta Frances National Marine Park is brimming with colourful sea life. Within a short boat ride, there are more than 50 dive sites to explore – including dramatic wall dives, a series of tunnels and caves, and dozens of wrecks – in the company of turtles, barracuda and eagle rays.

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Star Flyer cruise ship.
Experience cruising on the Star Flyer.

On land, expect blessed island scenery. There’s no shortage of pristine shores to roll out a beach towel – plus there’s rare wildlife to be spotted in Punta Frances National Park too. 

What makes Isla de la Juventud truly unique however is that it’s not just a mesmerising island for tourists and sightseeing, but it’s also home to around 100,000 Cubans – so you can still get an authentic taste of local Cuban life. Our top tip? Don’t miss El Ranchon – a local beach restaurant dishing up superb seafood.

Cayo Largo

Cayo Largo (‘Long Cay’) is pristine, beautiful and quiet – a natural paradise reserved just for tourists.

Being just 25 kilometres long and three kilometres wide, it maintains a down-to-earth and friendly vibe – perfect for those who like nature and want a non-commercial experience untouched by the ripples of mass tourism.

Naturists will be happy to learn there are a number of clothing-optional stretches perfect for getting that all-over tan. Beautiful Sirena Beach also stands out thanks to its peculiar oolitic sand, which means it always stays cool.

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Coral Cuba scuba diving.
There's a myriad of treasures beneath the water's surface.

Still want more chances to scuba dive in Cuba? There are 32 scuba diving sites and more than 200 sunken ships in the area.

In terms of locals, the only kind you'll meet here are nesting sea turtles, iguanas and enchanting flamingos. 

Cayo Rico

Looking at a map of Cuba, you may not even find Cayo Rico (‘Rich Island’). It’s among the most special, serene and isolated of Cuba’s many hidden gems – another awe-worthy stop in the necklace of coral islets scattered off the southern Cuban coast. 

The best part? You'll almost feel as though you have it all to yourself.

Framed by the same glimmering white shores and clear turquoise waters as Cayo Largo but with even fewer people around, this is the perfect place to play beach-worshipper all day long and hide away in picturesque coves.

Welcome to paradise. 


Sailing into Cienfuegos, you’ll quickly see why it’s dubbed ‘La Perla del Sur’ (‘The Pearl of the South’). It’s one of Cuba’s most beautiful cities and flaunts one of its most magnificent bays – a huge expanse lined by palm trees swaying in a salty breeze that, in Cuba’s heyday, came infused with the sweet scent of freshly crushed sugarcane.

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Palacio del Valle Cienfuegos Cuba.
Palacio del Valle was built in the early 1900s and is now a National Heritage Memorial in Cienfuegos.

Once the heart of Cuba’s roaring sugar industry, Cienfuegos flaunts some of Cuba’s most beautiful architecture thanks to the sugar barons that made their millions here.

They left their legacy in the form of stunning neo-classical facades, 19th century palaces and a superb collection of colonial-era buildings that stand impeccably well-preserved, barely diluted by modern construction.

In 2005 the city’s entire historic centre was declared a UNESCO World Heritage Site. Just one of the many highlights: Tomas Terry Theatre – where world-renowned opera stars Enrico Caruso and Sarah Bernhardt sang in the early 1900s – its gold-leaf mosaics and ceiling frescoes a sight to admire.

But Cienfuegos boasts many claims to fame. 


Cienfuegos is an enchanting seafaring stop on mainland Cuba.

Cienfuegos Botanical Garden is one of the oldest in the Americas, kicked off by a sugar magnate in the early 1900s with a fascination for exotic tropical flora; it’s home to Cuba’s longest street, Prado Avenue, flanked by beautiful buildings; and many would argue that Playa Rancho Luna is one of the country’s best beaches (it certainly won’t disappoint).

Keep looking and you’ll also discover an 18th century fortress, the former plantation of American chocolate baron Milton S. Hershey and waterfalls tumbling into crystal-clear pools in a lush tropical background that peters off into the distance.

There’s so much more to Cienfuegos than meets the eye upon that first glance of it rising on the horizon.

Experience the beauty and fascination of a cruise to Cuba with Star Clippers. Contact your local Travel Associates advisor for more information on Star Clippers sailings in the Caribbean and more.