Travel to Cuba and embark on an incredible sailing trip around the Canarreos Peninsula.

Spend eight unforgettable days sailing through the island paradise of Cuba. After being captivated by the time capsule that is Havana, venture offshore on a yacht for a Cuban encounter few people get to experience. Take in an array of natural wonders and get up-close to marine- and wild-life while sailing from Cienfuegos around the islands of Cayo Guano, Cayo Largo, Cayo Cantiles and many more. Uncover heavenly, untouched islands, swim in crystal-clear waters, snorkel over stunning reefs and spend days soaking up the chilled out vibe of irresistible Cuba. Find out why this vivacious country, so blessed with natural beauty and an abundance of cultural delights, is one of our favourite destinations.

Havana, Cuba
Havana, Cuba
Physical rating
Cultural rating
Min 15
Group size
Min 1 Max 8
Carbon offset
0kg pp per trip


  • Discover the vibrant contrasts of Havana
  • Wander cobbled laneways in timeworn Habana Viejo
  • Bask on the white sands of breathtaking Cayo Largo
  • Choose to visit Cayo Largo’s inspiring turtle sanctuary
  • Snorkel in the marinelife-rich waters of Cayeria Los Majaes
  • Say hello to the resident iguanas of Cayo Rico
  • Visit the fishing village of Cayo Cantiles
  • Indulge in delicious Cuban food at beachside restaurants


Get acquainted with Cuba's capital city, Havana. Walk through the crumbling splendour of World Heritage-listed Habana Vieja (Old Havana), or head to the Malecon to watch waves crash dramatically against the seawall. Alternatively, find a cafe, kick back with a Cuba Libre and soak up the procession of classic cars, the whiff of fragrant cigars and the constant sound of salsa, all melding effortlessly in this incredibly unique city.
Journey to Cienfuegos, a charming waterfront city known as the ‘Pearl of the South.’ Jump on board the yacht and set sail to Cayo Guano, where a lush tropical paradise, blue waters, coconut trees and some of the best sunsets on earth await.
Spend the next four days sailing the idyllic islands of Cuba, which are set among the world-renowned beauty of the Caribbean Sea. Visit Cayo De Dios and discover hidden beaches, untouched sands and pristine blue waters. Grab snorkelling gear to witness some of the Cuba’s magnificent underwater scenery and, if lucky, you may even spot a turtle or two. Relax and chill out on the deck of the yacht, bask in the glorious sunshine and soak up the laidback vibe of the Caribbean. Discover Cayo Largo, an island that boasts some of Cuba’s most beautiful coral reefs and where sugar-white sands dissolve into turquoise waters. Unveil the hidden gems of Cayo Los Majaes, Cayo Rico, Cayo Estopa and Cayo Cantiles, all of which stand out for their natural beauty. During the day, hit the water for a spot of swimming, snorkel with curious marine life, laze on white-sand beaches, relax on the boat and taste the flavours of Cuba. In the evenings, enjoy island style barbeques and unwind with new friends beneath shimmering stars.
We make the most of our last day on board with one last swim in the crystal clear turquoise before heading back to Cienfeugos.
Enjoy a final breakfast on board the yacht before heading back to Havana, where this unforgettable sailing adventure ends.
View trip notes to read full itinerary


8 breakfasts, 6 lunches, 6 dinners
Boat, Public bus
Guesthouse (1 night), Overnight boat (7 nights)


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Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

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Our Cuba Sailing Adventure trips score an average of 4.14 out of 5 based on 7 reviews in the last year.

Cuba Sailing Adventure , November 2015

Cuba Sailing Adventure , April 2015