Cuba Sailing Destinations

Cuba, after Covid exploring the island by yacht

So many things we would love to do after covid! Cuba is one of those places that is on many people’s travel bucket list. We love the Caribbean vibe and rich culture that Cuba offers, not to mention its stunning natural beauty and beaches to explore.

Mid-autumn to mid-spring

If you seek to enjoy Cuba in a not so typical tourist way, we invite you to take a sailing trip here. The best time to sail is mid-autumn to mid-spring since the summer months often experience more humid temperatures in this climate.

Red car in cube with tubber logo

The best time to sail is mid-autumn to mid-spring

It is hard to know where to start when planning a sailing vacation; however, Havana is a perfect starting place for visiting Cuba. The Hemingway Marina will always have a place for you to dock. The first time you arrive, you will be required to fill out some information so that you are ready to go and have the proper permits with you. 


There is a beautiful National Park located on Cuba’s Western tip that you simply cannot miss. You have to have a permit to sail around the Guanahacabibes National Park, but it is worth it for the view. The waters are shallow, and you will be able to see tons of turtles and other wildlife. Mind the coral reefs while you visit this part of the coast. 

Crystal clear waters and sandy beaches

A series of small islands past the Island of Youth (Isla de la Juventud) offer very secluded beaches. Be sure to stop at Cayo Largo and experience this former pirate hideout. The crystal clear waters and sandy beaches are so picturesque, and you can enjoy a day of adventure here. 

As you sail across the southern coasts past the Bay of Pigs, you can sail up to Cienfuegos’ port, which is also lovely and has a rich history behind it. You will notice a lot of unique architecture throughout and discover awesome beaches and more coral reefs here too. 

cuba Sailing

Simply breathtaking

Don’t miss the UNESCO world heritage town of Trinidad in Central Cuba. It is a few miles East of Cienfuegos and you can dock at the Casilda marina then walk or take a cab to the town. The colonial architecture here is simply breathtaking!

The port town of Manzanillo is another locale that we recommend you visit. This town is particularly famous for its Cuban cigars. Santiago de Cuba is the second biggest city in Cuba, so don’t miss out on the sights and endless adventures that are waiting for you here. Sailing around Eastern Cuba, you will eventually reach Maisi, which has a stunning lighthouse surrounded by a beautiful rocky landscape. 

The Northern coast of Cuba

The Northern coast of Cuba is an adventure of its own. There are so many beaches and coves that aren’t visited by the tourist crowds. Cayo Romano is one of those places and happens to be the largest cay in the Jardines del Rey archipelago. We recommend stopping here before heading back to Havana to end your trip.

Cayo Romano Lighthouse Cuba

Rent a boat with skipper in Cuba

Having a skipper on your chartered boat is a better option than getting a bareboat yacht here. Caribbean waters can be choppy at times, and a skipper will know how to navigate around the coral reefs surrounding the island. Be sure to prepare the boat with all the necessary supplies before you sail around this tropical paradise.