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Yacht sailing holidays & skippered tours in Cuba

Discover the magic of sailing holidays in Cuba! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture and gastronomy.




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Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Cuba

13 reviews

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New Year in Catamaran to Salsa rhythm


Birgit H.



Faccio notare che lo Skipper NON è stato "Fabio"
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Flottiglia di Capodanno a ritmo di Salsa con 2 catamarani!





Michele è una garanzia. Questa è la mia seconda volta con lui, e sto progettando di confermalo anche per l'estate 2018.
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Primo Maggio a Cuba! Sole mare e fiesta


Ettore S.



Vacanza stupenda organizzata alla perfezione, anche i brevi soggiorni a terra prima e dopo l'imbarco. Abbiamo visto le tipiche spiagge da cartolina dei Caraibi; fondali dai colori strabilianti che spaziano dal blu intenso al verde smeraldo all'azzurro acqua marina. Le escursioni di snorkeling ci hanno riservato piacevoli sorprese sia per la fauna sia per la flora della barriera corallina: corallo che sembra un ventaglio, ogni tipo di pesce; abbiamo avuto la fortuna di incontrare tartarughe marine, uno squalotto, pesci pappagallo enormi, una murena di almeno due metri, razze e mante, barracuda di ogni dimensione e dulcis in fundo un'aquila di mare. E' stata un'esperienza unica anche per il contatto umano con i cubani incontrati, per lo scambio di visioni differenti del modo di vivere e per la cortesia e disponibilità dimostrataci. Michele è uno skipper affidabile ed esperto che pone la massima attenzione ad ogni dettaglio infondendo sempre fiducia, nonché ormai un grande amico.
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Primo Maggio a Cuba! Sole mare e fiesta


Sabrina D.



Semplicemente perfetto

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8 reasons to choose Cuba to go sailing catamaran

  • Discover the beauty of Cayo Rico: rich fauna, exotic fish, baby blue waters, and stretches of beach and palm trees.
  • Enjoy the freshest of seafood as the sunsets beyond the ocean.
  • Kayak along the mangrove channels of the Quinto Canal.
  • Walk the charming streets of Cienfuegos - widely considered as one of the most beautiful Cuban cities.
  • Relax on the netting of a catamaran as you enjoy the fresh Caribbean sea air.
  • Experience the famous Cuban joy of life culture and different dances!
  • Taste a Cuban mojito - the national cocktail.
  • Fish in some of the best fishing waters around the Caribbean.

The best destinations to visit during your sailing holidays in Cuba:

The Cuban archipelago is made up of over 4,000 islands - with the main island of Cuba and the smaller, pine isle of Isla de la Juventud. Many of the islands are not widely known, this makes perfect for those looking to explore during their sailing holiday. Cuba is often referred to as the “Pearl of the Antilles”, a phrase coined by British painter Walter Goodman in 1873.

Aboard a sailboat or catamaran with a local skipper you will be well-equipped to discover all of the splendours of Cuba. See impressive mountain ranges that fall dramatically into the sea from your yacht. Explore the beautiful valleys and long beaches of fine sand. Experiencing Cuba by sailboat offers you the chance to explore regions that would otherwise be inaccessible. Cuba is a brilliant destination to embark on a memorable sailing holiday adventure.

Playa Flamingo

Located on the island of Cayo Coco, Playa Flamingo is a brilliant beach - one where you can swim, snorkel, and dive alongside the resident flamingos. A truly unique experience to be had during your Cuban sailing holiday.

Jardines de la Reina

This is an archipelago that was classified as a National Park in 1996. It is home to exceptional coral reefs and an active ecosystem of underwater life. The clear waters offers visibility to the striking nature of the key snorkeling and diving spots that lie below.


The beaches of Varadero in Cuba are famous throughout the world. What's more is that nearby you can find a rich abundance of things to do and places to see, including: El Nicho Waterfall, Bellamar Caves, and the Montemar Park that rests at the top of the Zapata Peninsula.

Tips to help you to better plan for your next sailing holidays in Cuba:

All you need to know about your sailing holiday around Cuba aboard a sailboat or catamaran.

The best time of year to explore Cuba by sailboat or catamaran is from October to April. Regarding budget, you can find all inclusive holidays in Cuba starting from approximately €1,300, plus your transport costs to get to and from the departure point, and other expenses that may be incurred, such as the cash float (that helps to cover variable costs eg. harbour mooring). Cuba’s international airports of Havana and Varadero are connected with major international airports worldwide.

Suggested sailing itineraries for your next holiday with a skipper in Cuba:

    A week of sailing around Cienfuegos

    Departing from Cienfuegos, where much of the regions historic monuments can be visited, you embark on to the islands and islets. Sail along to the mystical island of Cayo Largo and the famous, long reaching Playa Mal Tiempo that faces the coral reef of Cayo Rosario. At Quinto Canal stop for a kayak adventure, before returning to your port of Cienfuegos.

    View all sailing holidays in the Caribbean

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