A Guide To Sailing In And Around Cuba

Cuba is incapable of doing things by halves. Its port cities are bursting with Latin drama: the salsa, the mojitos, those cigars. Of course, there’s a dramatic history to uncover in its crumbling colonial architecture, too. For the nature lovers? The most biodiverse spot in the Caribbean brings with it Unesco-protected coral reefs teeming with more shark species than you knew existed. World-class diving happens in topaz waters, and there are miles of untouched coastline to explore. In a word, thrilling.

Sail around the Cuban coast in style, or spend longer discovering the Ocean Atlas by joining us on a Sailing Trip in the Bahamas or British Virgin Islands.

What to see and do

Before setting sail from Cienfuegos, it pays to have a look around. The Pearl of the South has some knockout architecture, best enjoyed with a stroll down waterfront Punta Gorda, followed by the neoclassical Paseo del Prado. Rum-infused sundowners at waterside Club Cienfuegos complete a special day.

The largest of Cuba’s coral cays, Unesco-hotspot Cayo Largo is destination one for snorkelling. The prettiest of the reefs is just off Playa Sirena, where you’ll bump into rays and a hammerhead shark or two. Onshore, flamingos and hummingbirds are arresting, but it’s the noble turtle that steals the show, nesting on beaches whiter than your charter’s sails.

Playa Sirena beach is up there with Cuba’s finest

And, of course, the capital Havana. Walk towards the first vintage American car you see and enjoy a chauffeured cruise along the legendary Malecón esplanade. Have your driver drop you at Hamel Alley in central Havana. It’s the best spot to imbibe the Afro-Cuban culture through street art and live rumba.

Best mooring locations

Marlin Marina Cienfuegos is the launchpad for your Cuban yachting adventure. While you’re there, be sure to spend some time at Club Cienfuegos, whose ostentatious architecture and white-glove service lend a golden-age atmosphere.

Marlin Marina is a quality mooring locale in Cienfuegos

If you drop anchor anywhere, stop between Cayo Anclitas and the Los Jardines de la Reina archipelago. What’s known as the Galapagos of the Caribbean, is an uninhabited wilderness with over 50 diving sites. Otherwise, don’t miss paradisiacal Varadero on the Hicacos Peninsula, where you’ll find Cuba’s most beautiful beaches.

Where to eat and drink

Between food shortages, and the insipid meals of its state-run restaurants, Cuba was known for its dismal dining scene. Things improved dramatically when private restaurants or paladares were first permitted in the ‘90s, though, and now quality cocina criolla is out there. Just up the road from Marina Hemingway in Havana is the venerable old La Fontana. It serves the city’s best barbecue food (careful, as portions are huge) and pairs it with live jazz. Not far away is El Rum Rum, which does a lip-smacking seafood stew. It also has both a wine and cigar sommelier. On the south coast, Cienfuegos’s Doña Nora on the Prado, dishes French flavours with silver service.

Paladar La Fontana is a private restaurant established in 1995 in Havana’s Miramar district

Where to get groceries

If you’re looking to load up before setting off from Cienfuegos, the nearest minimarket is Punta Gordo on the Paseo, which stocks dry goods in bulk, depending on availability. For fresh fruit and veg, you’re best off heading to the farmer’s market near Plaza José Marti.

Key annual sailing events

The only sailing event of note in Cuba is the Conch Republic Cup, a one-way, week-long regatta every May, from Florida’s Key West to Havana. American political pressure forced a hiatus in 2003, but the race – which aims to foster good relations between the two countries – started up again in 2016.

A race in full swing during Key West Race Week

Climate and weather

Reliable trade winds blow from the east, with a tendency to the north in winter and south in summer. Wind speed averages at 10 to 15 knots in winter and 5 to 10 knots in summer. Cuba’s tropical climate makes it agreeable year-round, though for consistent blue skies visit in spring. Hurricane season in Cuba runs from June to November, though Cuba experiences the lowest frequency of hurricanes in the Caribbean.

How to get there

The quickest and easiest way to Cienfuegos from Havana’s José Martí international airport is by car, which takes about three hours. If you’re travelling relatively light and want to keep spending down, take the direct trains (seven hours) or buses (five hours). The latter runs twice daily (7am and 10:45am).

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.