Start your journey off in colonial and colourful Havana, exploring the wonders this incredible city has to offer. Uncover more historic sites at Trinidad, a town boasting an old and charming Plaza Mayor and a lively atmosphere. Observe stunning wildlife in the Cayman Islands and enjoy the endless beaches Cuba has to offer. End your journey in UNESCO World Heritage Site of Cienfuegos, a city filled with magnificent colonial buildings. 

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Why We Love It

Experience close encounters with tame stingrays in Grand Cayman, home to the famous Atlantis submarine tour.

Visit the intriguing sites of Trinidad - charming Plaza Mayor, a lively bar in an 18th century church and a cave nightclub.

Explore Cayo Largo, the second largest island of the Canarreos Archipelago, a marine wildlife sanctuary for many species.

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Day by day Itinerary

Star Clippers Sailing: Havana - Cienfuegos

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Day 1


Arrive in Havana and explore the city.

Day 2


Continue exploring the city today.

Day 3

At Sea

Today is spent sailing at sea.

Day 4

Punta Frances - Isla de la Juventud

Oddly enough, there are both black sand and white sand beaches on Isla de la Juventud (once named Isle of Pines, because of the lumber that is harvested here). Punta Francis’ beach is the most famous, especially for diving and snorkeling. Isla de la Juventud was at one time a favorite haven for pirates and adventurers - Francis Drake, John Hawkins and Henry Morgan found refuge on these shores - prompting Robert Louis Stevenson to base his Treasure Island here. There are fascinating caves containing over 200 ancient Indian pictographs. You can also visit the skeletal remains of a huge 3-domed, semi-circular prison, now abandoned, where Fidel Castro was held before the revolution.

Day 5

Cayo Largo

With 28 kilometers of white sand beach, only 3 Kilometers wide and containing just a few small resorts, Cayo Largo recalls the Caribbean that used to be. The 2nd largest island of the Canarreos Archipelago is a marine wildlife sanctuary for many species. You’ll find turtle kraals where palm-sized hatchlings are raised to adult size and released to the sea, visit an island where iguanas roam freely and then bask in a natural swimming pool of the ocean, surrounded by dunes of flour-fine sand.

Day 6

Cayo Rico

Continue exploring Cayo Largo with a visit to Cayo Rico.

Day 7

George Town, Grand Cayman

It's amazing to realize that this once unknown small Caribbean island is now the center of once of the world's largest banking economies, the home of uncounted billions in offshore assets. Tax-free, duty-free and largely restriction-free, Grand Cayman is a magnet for money. Shopping is a full-time occupation here. But there is another side to Grand Cayman, where endless beaches, quiet lagoons and laid-back beach bars beckon. Grand Cayman was the first island to offer close encounters with tame sting-rays, and it is also the home of the famous Atlantis submarine tour.

Day 8

Cayman Brac, Cayman Islands

Christopher Columbus discovered Cayman Brac in 1503. He named it and departed, little knowing what wonders lay beneath the island’s shores. In Bloody Bay,1000 feet of nearly vertical cliff wall descend to the ocean floor, making it one of world’s premier diving experiences. It was first explored and made famous by Jacques Cousteau, but today even novice divers can marvel at the amazing variety of fish, corals and other marine life that make their homes in nooks, crannies and cavities at every depth on the wall. If you prefer your sightseeing above, a pond on Cayman Brac holds a huge rookery of red-footed boobies – probably the largest in the world.

Day 9

At Sea

Spend today sailing at sea.

Day 10


When you gaze at the lovely neo-classical homes and elegant public buildings lining the Prado, Cienfuegos mile-long main boulevard, you can see the Empire origins of this gracious city on the Bahia de Cienfuegos. Founded in 1819 by French immigrants, Cienfuegos is a World Heritage Site which, because of the relative isolation of Cuba, has escaped the ravages of many modern cities. Architectural highlights of the city and nearby Punta Gorda include the fanciful Palacio de Valle, the Jagua Fortress, the luxuriant Jardin Botanico, the Cathedral and the Victorian-era yacht club.

Day 11


End your journey off in Cienfuegos.

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