Previously closed off from the world, Cuba has remained frozen in time, giving it a one-of-a-kind culture filled with life, music, and color. Here you’ll find a deep and rich history, gorgeous beaches, and wonderfully unique art and architecture. There’s plenty to do and see on the island, and our Cuba Sailing Itinerary is designed to show you the best of this Caribbean paradise.

Our Guide to the Cuba Sailing Itinerary

The largest island of the Caribbean, there’s an abundance of beauty on the island of Cuba. With over 300 white sand beaches, crystal clear blue waters, and quaint coastal towns, Cuba has exactly what you need for a lovely getaway.

While Cuba may be full of beaches, be sure to enjoy everything else Cuba has to offer. During your trip be on the lookout for crocodile swamps, abandoned coffee plantations and mountainous terrain and trails. Cuba is also home to rural villages and urban cities, where you can find usual art studios, and cosmopolitan luxuries.

With all the wonders that Cuba holds, you can be sure our Cuba Sailing Itinerary will offer a vacation of a lifetime in one of the most vibrant places in the world.

Getting There

The best way to get to Cuba is via plane. You can find many international flights flying into Havana's José Martí International Airport. In recent years air traffic to Cuba has increased so much, you can easily find direct flights from many places in North America, Europe, and South America. Once you land, you will need to take a taxi to downtown Havana. This should cost between 25-30 CUC.

Keep in mind that if you are from North America, Europe, and South America, you will need a Tourist Card from the Cuban Government in order to enter the country. However, you can usually purchase the Tourist Card when you buy your plane ticket. Travelers from anywhere else will need a visa to visit Cuba.


The best time to visit Cuba is between December and May. This time of year will bring sunny, dry weather - for perfect sailing conditions. Weather in Cuba is fairly typical of the Caribbean and heavily influenced by trade winds. We recommend going during the dry season as this is when temperatures are pleasant and humidity is down.


Mooring on the Cuba Sailing Itinerary primarily consists of small cays where you can anchor and "free-swing" for the evening. Without many amenities, these are nice free options where you will be safe and sheltered. Make sure you pack plenty of provisions, so you'll have everything you need for your trip.