Sail to paradise and back again on a cruise around the Cuban islands of the Canarreos Archipelago.

After getting your fill of Havana’s vibrant Old Town and spicy nightlife, leave it all behind on a voyage around the stunning Canarreos Peninsula. Each uninhabited island provides a new adventure, from sun and sand and crystal waters, to monkeys, iguanas and cute little hutias. The balmy waters are a snorkeler’s dream, with loggerhead turtles, manta rays and countless colours of fish all on display. Or simply throw down a towel and soak up the sun on some of the best beaches in the world.

Our Bahamas sailing tours

9 Days From R26,410

Set sail across the Caribbean Sea to visit the untouched and idyllic islands of Cuba. A...

Highlights of sailing in Cuba

Havana

The living time-capsule of Havana is one of the most unique cities of the modern world. Walk streets lined with classic American cars and crumbling colonial architecture. Experience Havana’s beautifully preserved Old Town, Habana Vieja, and drive down the Malecon, a 7-kilometre (4 mile) seaside strip.

Cayeria Los Majaes

Cayeria Los Majaes is a small group of islands ideal for basking on sun kissed beaches and snorkelling clear waters. The pools surrounding the islands are less than a metre deep, with temperatures that average around 30C (86F). A myriad of marine life frequents the warm waters, and you might even spot the large colony of iguanas that live on the shores.

Cayo Alcatraz

It’s not hard to imagine the white sands and clear blue waters of Cayo Alcatraz. As tempting as it may be to simply catch some sun on the beach, the shallow surrounds of this uninhabited island are perfect for snorkelling, offering a chance to find stingrays and manta rays alongside a kaleidoscope of colourful fish.

Cayo Cantiles

Cayo Cantiles is largely uninhabited, save for the three workers who tend to the monkey sanctuary. The island has been named a biological centre for preservation, and although it’s earned the nickname ‘Monkey Island,’ you’ll also get the chance to spot iguanas, and the curious hutias that call the island home.

Our boats

Orana 44

This spacious catamaran provides smooth sailing through Cuban waters. The sundeck up top is perfect for basking with a cocktail, while the twin-hull provides plenty of room below deck as well. The Orana 44 has four twin-share cabins complete with ensuite, a communal saloon with panoramic windows and a cockpit ready-made for drinking and dining.

Learn more about Orana 44

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Read more about Cuba