Your Sailing Itinerary in Cuba. One-Week Route

The magic of the Caribbean extends between the two Americas and Cuba offers an incredible sample of its charming: intense blue waters, white-sand beaches, and palm trees emerging from the shores. Undoubtedly, it is a faithful portrait of the most tropical sea in the world, in which it is summer every day of the year. What better way to enjoy it than following a sailing itinerary in Cuba and its famous Cays?

Actually, it is not only the island of Cuba that worth a visit since all around there are more than 4.000 islets called Cayos and the Juventud Island, where you can relax and get in touch with nature. On its large surface, it encloses 600 beaches and a stunning natural diversification that encompasses mountains, plains, caves, rocks, forests, and 14 national parks. Then, if you also wish a more “urban” experience, you can meander through its rural villages or more cosmopolitan cities.

Do you want to learn more details about what Cuba and discover why it is a renowned sailing destination? Then, keep reading this sailing itinerary in Cuba that starts from Cienfuegos and explore the most beautiful Cays. But first, let’s have a look at the sailing conditions!


Cuba has a sub-tropical climate with two distinct seasons, the dry season, which is the winter, and the summer, or the rainy and muggy season from May to November. The mean temperature in winter is 77º F (25º C) whereas in summer it can reach up to 82º F (28º C). June, July, and August are the hottest months when the heat is intense, and the humidity can be unpleasant. Cuba is heavily influenced by trade winds, but September and October are the months with the highest probability of hurricanes.

Sailing Conditions

The best time to navigate in Cuba is from November to May when you can find the best sailing conditions. Winds blow almost from north-east between 15-20 knots, but they can vary from 5 to 30 knots.

One-Week Sailing Itinerary in Cuba

Day 1. Cienfuegos

red vintage car with Cuban cigars on the floor

This sailing itinerary in Cuba kick-off couldn’t be better because at the colourful base of Cienfuegos you will find your boat. After the check-in, we strongly recommend a walk across its vibrant streets. The “Pearl of the South”, as it is called Cienfuegos, has been appointed as a Unesco World Heritage since 2005. Besides the recognizable French colonial architecture, it displays a great variety of street food, traditional and trendy boutiques, top-quality restaurants that fill up its sidewalks and bustling waterfront.

If you have time, we also suggest renting a typical Cuban taxi to visit a bit of the inland. The Nicho waterfalls could be a great option to have your first Cuban dip! If you want to start sailing straight away, you can directly head to Cayo Guano del Este anchorage. Here, admire its famous lighthouse and swim in its shallow water plenty of coral to start your first session of snorkelling of your sailing trip.

Day 2. Cayo Largo

The next day head to the mysterious Cayo Largo. Why mysterious? Because it’s rumoured that once upon a time it was a pirate shelter where they buried hidden treasures. Wheater it is a pure legend or if there is a kernel of truth, one thing is sure: that once arrived at Cayo Largo you will already find one of the real treasures of the Cuban archipelago!

Cayo largo is a small limestone cay plenty of wonderful beaches. Make sure to visit Playa Sirena and Playa Paraiso, but then keep exploring to discover which one you will like most. The Cay offers many scenic restaurants and bars on the various seafronts where you can try a delicious grilled fish.

Cayo 3. Cayo Los Ballenatos

Beach of Cuba with a colourful boardwalk and palm trees on both sides

On to the next day if this sailing itinerary in Cuba! Follow Quinto Canal where you will find a sandbank surrounded by a natural swimming pool. Sail onward, because what is waiting for you today is Cayo Los Ballenatos.  Take some time to do snorkelling because it seems it has been created for delighting marine life enthusiasts. here you can overnight, but you can spend the night at Quinto Canal or at Cayo Largo.

Day 4. Cayo Rosario

On day 4 make for another popular snorkelling and diving destination, Cayo Rosario. This Cay is an uninhabited island, or better, it is inhabited only by iguanas. But besides being the iguana’s home and of a variety of tropical fish and shells, it is popular for its long stretch of pink sand beach. If you have ever wanted to totally relax on a desert island, well, you’ve found it! Now we’re halfway through our sailing itinerary in Cuba, but don’t worry because you’ll have other opportunities to sunbathe on another idyllic island.

Day 5. Cayo Estopa

sandbank in Cayo Largo surrounded by shallow crystal clear water

Welcome to Cayo Estopa! It is a small island with a shallow beach of a coral reef. Here you can swim and do some great snorkelling for then going to Cayo Rico, another uninhabited island with only a “hamlet” of iguanas and one restaurant near the jetty famous for its lobster.

Day 6. Cayo Largo

Return to Cayo Largo and if you haven’t visited it before, visit the “Sea Turtle Hatchery”. This is a sea turtle rescue centre where you can learn more about this endangered species and their protection. But don’t live Cayo Largo without eating in one of its restaurants on the beach where you can order fresh shrimps and lobster.

Day 7. Cienfuegos

Our sailing itinerary in Cuba has come to an end. It’s time to head back to Cienfuegos and do the check-out at the base.

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