Sailing in Cuba


‘The clouds were building up now for the trade wind and he looked ahead and saw a flight of wild ducks etching themselves against the sky over the water, then blurring, then etching again and he knew no man was ever alone on the sea.’
~ The Old Man and the Sea, Ernest Hemingway
Sailing in Cuba is an unchartered adventure with more challenges than your average Caribbean island, but much more adventure on the high seas. If you prefer to sail your own vessel, it is a six-hour fair weather journey from Quay West to Cuba, taking you through the Gulf Stream, across the shadows of container ships accessing the Panama Canal and in sight of the mountains of Matanzas. As you approach Havana from El Morro castle we will be waiting to take care of all your requisite paperwork and customs formalities. It is such a civilised way to arrive in Havana. If you prefer to be skippered, you can charter yachts manned by experienced captain and crew (including luxuriating on a 60-meter custom-built Benetti with a Michelin-starred chef, starlit cinema, spa and private nightclub). Discover deserted sand specks and drop anchor for the night in a protected canal to lie on the deck and watch the sky ablaze. Watch in awe as your skipper dives into the water, harpoons a lobster and prepares a fresh feast before your eyes.

Cuba Private Travel is one of the most experienced luxury private travel companies on the Caribbean island of Cuba. Our owner and managing director is the respected local expert, Irish born Johnny Considine, who lives in Havana and has more than fifteen years experience arranging vacations in Cuba.
We hope that exploring the travel ideas on our website will inspire you to come and visit the beautiful island that we know and love...

The best tailor made travel and vacation experts in Cuba

‘The Irish born Cuba expert
lives on the island 8 months of the year and has the edge on the gold rush happening now...’
‘Johnny Considine is on pretty much first name terms
with the whole population and putting your holiday in his hands means you can travel with the gusto of a backpacker...’

The best things to do in Cuba and our travel tips

The Cuba Private Travel team has access to the very best in Cuban art, music, literature, dance, environment, history and architecture as well as Cuba’s most outstanding beaches and accommodation. By listening to you, the independent traveller, we are able to create tailor-made travel itineraries for your vacation that take you to the heart of Cuba’s culture, landscape and people. Cuba Private Travel’s bespoke itineraries are fully U.S. Treasury Department compliant and include access to personal guides, experts, interpreters and, of course, a 24-hour concierge.
Delve deeper and be inspired about what to do in Cuba and discover some of the best travel advice for the island...

Travel Ideas

Concierge Suggestions

Havana Gazette