Cuba Sailing Itinerary

Discover the Largest Island in the Caribbean and Step Back in Time With Our Cuba Sailing Itinerary

Cuba Sailing Itinerary

Sail through the Caribbean Island of Cuba

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, perfect for a Cuba sailing itinerary. 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 a Cuba Sailing Itinerary

The largest island of the Caribbean, beauty is abundant 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 Cuba sailing itinerary.

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 you can find on a Cuba sailing itinerary.

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 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.


  • Weather

    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 on a Cuba sailing itinerary during the dry season as this is when temperatures are pleasant and humidity is down.

  • Mooring

    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.


Top 7 Places to Visit in Cuba

Cuba Sailing Itinerary

Day 1


One day one, you’ll pick up your yacht at home base in Cienfuegos, to start your Cuba sailing itinerary. One of the most colorful spots in Cuba, French colonial architecture is sure to wow. Appointed as a UNESCO World Heritage site in 2005, Cienfuegos is Cuba’s “Pearl of the South.” Restaurants and bars are abundant in this elegant city.

Recommended Restaurants and Activities: 

Day 2

Cayo Largo

On to the next stop, on day two of your Cuba sailing itinerary – Cayo Largo! Once upon a time, this bay was a pirate pit stop; it’s rumored to hold buried treasure. If you believe that, you can spend the day exploring beneath the water’s surface! Playa Sirena is the perfect beach for snorkeling and sunbathing.

Cayo Largo is said to have Cuba’s best beaches, spend some time exploring and see which beach you like best!

Recommended Restaurants & Activities:
  • Playa Paraiso, Cayo Largo, Cuba
  • Bar de Plage Chiringuito, Cayo Largo, Cuba

Day 3

Cayos Los Ballenatos

On day three of your Cuba sailing itinerary, make your way to Quinto Canal first. Here you’ll find a natural pool, filled with water warmed by the sun. Next, you can sail to Cayos Los Ballenatos, where there is a magnificent coral reef. We recommend you spend some time snorkeling, immersing yourself in the vivid undersea culture.

Return to Quinto Canal or Cayo Largo for a good overnight anchorage.

Recommended Restaurants & Activities:
  • Parque Nacional Cienaga de Zapata, Cuba

Day 4

Cayo Rosario

After a busy day at Cayos Los Ballenatos, head to Cayo Rosario. This uninhabited island is a great spot for total rest and relaxation. Enjoy the wildlife of Cuba, as this is also a well-known iguana residence.

Cayo Rosario gets its name from the long stretch of fine pink sand. Take a stroll and keep your eyes peeled for shells.

Recommended Restaurants & Activities:
  • Snorkeling and Diving, Cayo Rosario

Cuba Sailing Itinerary

Cuba is Filled With Beautiful Beaches and Places to Discover on a Cuba Sailing Itinerary

Day 5

Cayo Estopa

Day 5 of your Cuba sailing itinerary, it is now time to spend the day in Cayo Estopa. Another pink sand beach, you’ll love relaxing here with iguanas roaming the beach. Day Five is a day best spent chilling out and exploring all the natural beauty Cayo Estopa has to offer.

Recommended Restaurants & Activities:
  • Swimming and Snorkeling, Cayo Estopa, Cuba

Day 6

Cayo Largo

It’s time to return to Cayo Largo. One of the best things to do on the island is dining on the beach. Here there are plenty of beach restaurants and grills where you can enjoy super fresh and delicious seafood!

Normally a tranquil sanctuary, devoid of wild clubs or discos, the village in Cayo Largo will have a weekly fiesta on Fridays during the summer months. Be sure to partake in the merriment and fun, as Cayo Largo is known for its easy-going, down-to-earth atmosphere.

Recommended Restaurants and Activities:
  • Taberna del Pirata, Cayo Largo Marina, Cayo Largo, 25300, Cuba

Day 7


On the last day of our Cuba sailing itinerary, it’s time to head back to Cienfuegos to check out. You can return your boat at the base.

If you’d like to extend your vacation, there’s plenty to do in Cienfuegos. We recommend you stay and explore the city. Or if you have the time, you can return to the main island. There, the best places to see include La Havana, the capital, Viñales, a tiny town in the west of the island, and Trinidad, said to be the most historic city in Cuba – apart from Havana. 

Recommended Restaurants and Activities:

Call Us Today To Book Your Cuba Sailing Itinerary

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