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 $2,385

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

Reviews

Egypt Experience, September 2018

Brittaney Hastings

Best of Argentina, Uruguay & Brazil, September 2018

Divya Ragoobeer

Highlights of Central Europe, August 2018

Vanessa Dela Paz

Best of Alaska, September 2018

Hans Oliver

Andorra: Hike, Bike & Raft , September 2018

Julia Buckel

Inca Trail Express, September 2018

Megan Gilbertson

Egypt Adventure, September 2018

Hayley Baird

Cape Town to Vic Falls, August 2018

Kevin Barker

Jordan & Egypt Express, September 2018

Rhia Catapano

Mount Toubkal Trek , August 2018

Lisa Sipocz

Cycle Tanzania, September 2018

Tom Palmer

San Francisco to Las Vegas, September 2018

Duncan Shaw

Vegas to San Fran, September 2018

Bernhard Trost

Vegas to San Fran, September 2018

Alister Galpin

Vegas to San Fran, September 2018

Lucy McAuliffe

Vietnam Express Southbound, August 2018

Mark Rose

Explore Jordan, September 2018

Rosemary Cozens

Balkan Adventure, August 2018

Cornelia Kea Hoppe

India's Golden Triangle, September 2018

Melanie Eggleton

Egypt Experience, September 2018

Cameron Rosenbalm

Gorillas & Game Parks, August 2018

Jennifer Richards

Balkan Adventure, September 2018

Patricia Keane

Amalfi Coast: Hike, Boat & Kayak, September 2018

Mary Begg

Stone Town to Vic Falls, August 2018

Laura Jojoa Cruz

Best of Turkey, September 2018

Marion Kelly

Peru Encompassed, August 2018

Noel Carter

Egypt Experience, August 2018

Melissa Haluszczak

Morocco: Hike, Bike & Horse Ride, September 2018

Jonathan Mann

Bangkok to Singapore, August 2018

Heather Hill

North Morocco Adventure, September 2018

Patricia Wallenburg

Explore Jordan, September 2018

Rosemary Cozens

Beijing to Moscow, July 2018

Ruilin Shi

Bali & Lombok: Hike, Bike & Raft, September 2018

Sebastian Dille

South Africa Family Safari with teenagers, August 2018

Brenda Maguire

Okavango Experience, August 2018

Julie Lowe

A Taste of Scandinavia, July 2018

Louise Dickson

Read more about Cuba