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Sailing trip through Cuba​

Travel time

15 days

distance

Stations

4 places

Activities

10

Travel type

Sailing trip

Juan Carlos
CUBA TRAVEL SPECIALIST

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Get ready to experience the best of Cuba, where tropical landscapes and turquoise waters come together for the perfect getaway. Our exclusive sailing trip package offers a seamless combination of land exploration and ocean adventures, giving you the chance to dive into Cuba’s vibrant culture before setting sail through the Caribbean’s crystal-clear waters.

Introduction

Picture yourself gliding through the turquoise waters of the Caribbean, passing by tiny islands with white, palm-fringed sandy beaches—this is what a sailing trip in Cuba is all about. With a coastline stretching over 3,570 miles (5,745 km), Cuba is a sailor’s paradise, dotted with hidden bays and countless offshore islands. These waters are home to the world’s second-largest coral reef, making the journey as vibrant as it is scenic. Aboard a comfortable catamaran, you’ll experience the best of Cuban island life. Swim on pristine, white-sand beaches, watch the sun dip below the horizon in unforgettable Caribbean sunsets, and dive into crystal-clear waters for some of the best snorkeling and diving imaginable. It’s the ultimate tropical adventure—what more could you ask for?

HIGHLIGHTS

Your recommended itinerary

On your sailing trip, you will first explore the old town of Havana and can choose from many activities in the capital to enjoy its full charm. As you continue to Trinidad and Cienfuegos, you will discover the Cuban colonial style and be able to admire some of the most beautiful buildings in the country. On the 8th day, your sailing trip begins with a trip through the numerous small island groups of the Canarreos archipelago. Be prepared for lots of swimming and snorkeling!

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Day 1-4 : Havana - Rome of the Caribbean

CULTURE

COUNTRY & PEOPLE

SOCIALISM

We will be waiting for you at the airport to take you to your accommodation. A long-haul flight can be very tiring. After your flight, take your time to arrive and acclimatize.

On day 2, we recommend an exciting city tour through Havana. You will explore the famous old town on a city tour with a German-speaking guide before getting to know the outskirts from the window of a genuine vintage car after a delicious lunch. A must when visiting the capital!

The third day is at your leisure. Let yourself be overwhelmed by the charm of Havana. The Rum Museum of the Havana Club, the market hall with many stalls or the famous Malecón – we know many great places and have the right tips for you. Today you can also take a trip to the tobacco valley in Viñales or to the orchid garden in Soroa.

Day 5-6 : Trinidad - UNESCO World Heritage Site

COUNTRY & PEOPLE

CULTURE

BEACH

On day 4, you leave Havana and drive towards Trinidad. Trinidad offers the potential for numerous excursions, but you can also spend a good day on the beach. You should definitely not miss a walk through one of the most interesting colonial cities in Cuba. Or maybe you would like to be driven around in a bicitaxi? Plan the days as you wish and enjoy the really special atmosphere in Trinidad. The city has been declared a national monument and UNESCO World Heritage Site.

Day 7-8 :Cienfuegos - Pearl of the South

WATER ACTIVITIES

RELAXATION

CULTURE

You will then continue on to Cienfuegos. Cienfuegos will certainly surprise you as you pass through, as the urban style stands out from that of other Cuban cities. Some of the most beautiful buildings in the country can be admired here. You can also expect a phenomenal view over the most spectacular natural bay in the country. The nautical city is one of the newest settlements in Cuba and has so far been relatively untouched by tourism.

Day 8-15 : Your sailing trip begins today!

WATER ACTIVITIES

This route starts in Cienfuegos and heads west past numerous small island groups in the Canarreos archipelago, which are ideal for diving, snorkeling and swimming. The return to Cienfuegos begins from the last stop, Cayo Largo. This option is ideal for those who do not have more than a week for a sailing adventure.

Day 15 : Return flight from Havana

FLIGHT

Unfortunately, your sailing holiday comes to an end today and you will travel with our private transfer to Havana airport, where you will begin your return journey to Germany. You will fly home full of new impressions and wonderful memories. Have a nice flight!

Travel FAQ

Frequently asked questions from our travelers

For many travelers from the US, Cuban food may seem carb-heavy, with a focus on meat and limited servings of fresh vegetables, salads, and fruit. Spicy, sour, and salty flavors aren’t common in Cuba, but sweet treats are easy to find. That said, Cuba’s food scene offers plenty of gems, especially at paladares—private, family-owned restaurants known for their rich and flavorful dishes. Be prepared, though—prices at paladares can be a bit steep compared to what locals typically pay.

Hotel dining is usually more affordable, but the quality can be inconsistent. A warm welcome often comes with a mojito in hand, and you’ll find that this iconic Cuban cocktail typically costs around $2.25 to $5.75. Local beer is budget-friendly, ranging from $1.10 to $2.65, and a good bottle of Cuban rum can be yours for as little as $7.50.

When it comes to water, while some travelers drink tap water without issues, we recommend sticking to bottled water just to be safe. You’ll find canned and bottled drinks at stores for $0.45 to $1.40, while in bars and restaurants, prices range from $1.00 to $2.90. Whether you’re sipping on a mojito or tasting Cuban desserts, get ready for a culinary adventure!

Yes. You will also need a document written in Spanish confirming the validity of this international health insurance.

Without this, you may be refused entry. Ask your insurance company; they can issue you with this confirmation. We can recommend Hanse Merkur, ADAC, ERV or Allianzversicherung, for example. Experience has shown that nobody usually wants to see the document, but if you unexpectedly have to see a doctor, it is important to be able to present the receipt.

You can read more about the entry requirements here .

Climate information: You should expect a hot, subtropical climate in Cuba all year round. A constant wind moderates the heat. In summer there is more rainfall than in winter and temperatures are around 25-30°C. In winter around 20-25°C.

Best time to travel: November to April.

The main travel season in Cuba is from mid-November to mid-April. The temperatures are a little lower during this time than in the other months, although there are generally very little temperature fluctuations in Cuba. The temperatures are between 25°-28° with a water temperature of 25°. From November to around March/April it is also tobacco season and you get a great insight into the tobacco harvest.

Cuba can experience heavy rainfall, tropical storms and sometimes landslides from June to November (hurricane season). We recommend that you follow regional weather forecasts and heed the advice of local security authorities during your trip.

Current information is available online at www.nhc.noaa.gov and www.weather.com.

You can find more information about the best time to travel here .

For round trips within the country, foreign tourists primarily consider buses (Viazul), organized bus tours, but also rental cars, although bus trips are less problematic in terms of road safety.
Cuba is suffering from power shortages. In order to save electricity, power cuts are carried out, especially outside of the tourist centers (important for individual travelers!), which can also lead to disruptions in the water supply and communication.
Cubans require a permit from the authorities for any kind of private business. For this reason, and because of the risk of robbery, private taxis that do not belong to an official taxi company and are not marked accordingly are expressly warned against. Likewise, you should ask for official permission before staying in private homes (even if you are an acquaintance), otherwise both parties (host and guest) risk getting into trouble with the police.
Casas Particulares: In Cuba it is different from most countries in the world. A Cuban is not allowed to simply accommodate tourists in his house. To do this, locals in Cuba need a license. Anyone who acquires this license is allowed to rent out rooms in their house and call their home a “Casa Particular”. All Casas Particulares are registered and can be recognized by the white/blue sign on the outside wall. Here, as in every hotel, all travelers are noted. The families need your ID and your tourist visa for this. The state hotels are an alternative if you are looking for a place to sleep. But not for gaining an insight into Cuban culture.
Travelers should make copies of their documents and keep valuables in different places or in a safe.
It is best to avoid taking photographs of queues of shoppers, dilapidated houses, etc., as the people involved may react angrily. In addition, military facilities (restricted areas and buildings) and official vehicle convoys may not be photographed. Not all military facilities or restricted areas in Cuba are fenced off or clearly recognizable as such. Instructions or requests from guards and security personnel should be followed without fail.
Smoking is prohibited in enclosed public spaces (e.g. shops, cinemas, offices, taxis, buses). In restaurants, smoking is only permitted in specially designated smoking areas.
“Even if small quantities of drugs are found for personal use, drastic penalties can be expected. Possession of small quantities by foreigners is also punished as drug smuggling. The penalty for this is four to thirty years in prison, and in particularly serious cases the death penalty is imposed. For criminal prosecution following traffic accidents, see above under road traffic.
Visitors should refrain from political activity, as this can be punished with long prison sentences.”

If you have any questions or problems during your trip, first contact the emergency numbers provided in your travel documents. You can reach our office in Havana at this number. If you have any questions for the Cuban Embassy, ​​you can use the following contact details:

In Germany

Embassy of the Republic of Cuba

Stavangerstrasse 20, 10439 Berlin

Email: consulberlin@t-online.de

Homepage: www.botschaft-kuba.de

In Austria

Embassy of the Republic of Cuba

Kaiserstrasse 84 Vienna 1070

Email: secembajador@ecuaustria.at

Homepage: www.ecuaustria.at

In Switzerland

Embassy of the Republic of Cuba

Gesellschaftsstrasse 8, Bern 3012

Email: consulcuba.berna@bluewin.ch

For emergencies that need to be dealt with locally, such as if you have lost your passport, you can always contact your respective embassy in Cuba:

German Embassy Havana

Embassy of the Federal Republic of Germany

Calle 13, No. 652, esq. B, Vedado, Havana, Cuba

Phone: +53 7 833 25 69

Emergency telephone number: +53 5280 5942 (can also be reached via SMS and WhatsApp if necessary)

Swiss Embassy in Cuba

Embassy of Switzerland

5ta Avenida no. 2005, between 20 and 22, Miramar, Playa, Havana, Cuba

Phone: +53 7 204 26 11

Austrian Embassy Havana

Embassy of Austria

Avenida 5ta A No. 6617, esq. a calle 70, Miramar, Havana, Cuba

Phone: +53 7204 28 25

It is advisable to take a supply of cash in euros with you. You can also withdraw money from ATMs using credit cards. However, depending on the current availability of cash, this can involve waiting times. It is therefore advisable to carry enough cash with you. With the right credit card, withdrawing money abroad is even free of charge. It is advisable to take several credit cards with you. In general, Visa cards work better at ATMs than Mastercards. If withdrawing money from ATMs does not work, it is possible to withdraw money at the bank counter by presenting your passport. However, this often involves long queues. Credit cards from US credit companies are generally not accepted at ATMs. It is therefore advisable to stock up on enough cash, as you should not rely on the number and functionality of ATMs in Cuba.

Set Sail on a Cuban Adventure

The sea is undeniably a key part of Cuba’s magic, captivating visitors with its beauty and tranquility. If you’re seeking a truly exclusive experience, we recommend pairing your trip to Cuba with an unforgettable sailing journey along its stunning coastline.

Sailing in Cuba is your gateway to tropical paradise. Picture yourself gliding through crystal-clear waters, surrounded by rich marine life, vibrant coral reefs, and secluded islands boasting pristine, white-sand beaches. Each moment offers a new discovery—whether you're swimming, snorkeling, or simply soaking in the view from your boat.

However, this sense of solitude and untouched beauty is largely preserved due to Cuba’s strict sailing regulations. But don’t worry! We’re here to help you navigate these rules and ensure that you experience this idyllic adventure in the most seamless and stress-free way possible.

Let the Caribbean breeze guide you to your dream Cuban escape!

Take the wheel.

Please keep in mind that the Caribbean has rough waters and reefs abound, so if you want to travel in a relaxed manner, it is best to rent a boat with a crew.
Rent a boat with crew
Leave the worries mentioned above to them and dedicate yourself fully to one of the best experiences of your life. In this case, the ports are determined in advance and an itinerary is planned. In return, however, you will receive the attention of an entire crew who will even help you prepare meals. Take a look at the possible options and choose the one that best suits your dream vacation.
Forget all your worries and relax. The climate in Cuba is perfect for those who like water activities. This is especially true between November and April. The average temperature is usually 25 degrees, in some places a little higher. Another advantage of exploring Cuba by boat is that this tour will certainly take you to places away from mass tourism.
Sailing tour from Havana
In the capital city of Havana you can find several companies offering sailing trips. These are located either in the port of Havana or in the popular “Marina Hemingway”. For some people this is the starting point for their adventure trip along the Cuban coast. Just remember that regardless of which port you choose, the authorities there will certainly have some guidelines for shipping permits and other formalities for you.
From Havana you can discover the charms of Guanahacabibes National Park. Most travelers arrive by land, but visiting from the sea offers a much more exclusive experience.
With its shallow waters and numerous lakes, it is not surprising that this is a popular spot for sea turtles. There are conservation projects for these animals and they are present in large numbers at certain times of the year.
The corals there are very fragile and the marine flora and fauna are particularly protected, so you will probably need a special permit to sail there. While you are in the area, you might as well plan a visit to Maria La Gorda. It is rumored to be one of the most beautiful places in all of Cuba.

The hawksbill turtle in Cuba is a rare species.

The most beautiful sailing destinations
There are several destinations in Cuba that you can visit by catamaran. One of the most exciting places to sail in Cuba is the Canarreos archipelago. It is located south of the central part of the country. The fact that there are not many sailboats is one of the reasons why a trip here is very special.
Various cays of this archipelago, such as Cayo Largo and Cayo Cantiles, as well as spectacular places such as Playa Sirenas and Canal Quinto, are waiting for you here. Don't miss this opportunity!
Cayo Largo is one of the most famous cayos in this archipelago, thanks to its fine white sand and crystal clear waters where you can observe numerous marine species.
This is the ideal place for snorkeling and diving. Of course, it is also suitable for other water sports. Sport fishing is also allowed on this type of excursion. But it is just one of the many activities offered in conjunction with a boat trip in Cuba.
From Cienfuegos you can take sailing trips to Cayo Guano, Punta del Este or Cayo Sal.

Discover Cuba on a sailing trip with Cuba Buddy.

This type of excursion, which lasts around 8 hours or more, usually includes extras such as a nightly dinner, scuba diving equipment and other water sports. These itineraries also often offer the opportunity to swim with dolphins, kayak in the mangrove canals or swim in natural pools.
A little further east of the island, you can walk along the coasts of Maisí, famous for the La Concha lighthouse. You can even see the lighthouse from your deck. It is a landscape unique in Cuba, characterized by its rugged surroundings.
The sailing trips in Cuba are exclusive and offer you the opportunity to go on an adventure, a romantic trip or a family trip. No matter what you choose - we are sure that you will have a great experience!
Private yacht in Cuba
If you own a private yacht, you can enter Cuba through any of the eight international ports with a customs service.
• Marina Hemingway (Havana)
• Marina Dasena (Varadero)
• Cienfuegos Marina
• Cayo Guillermo Marina
• Santiago de Cuba Marina
• Puerto de Vita (near Guardalavaca in the province of Holguín)
• Cayo Largo del Sur
• Cabo San Antonio (westernmost tip of the province of Pinar del Río)
Boat owners should contact the Cuban Coast Guard on VHF 16 and 68 or the tourist network 19A . Once in the country, you can continue to sail around the islands of the archipelago with prior authorization from customs authorities. Always follow the laws established for navigation in Cuba.

Sail between beautiful islands in the turquoise Caribbean.

Yacht charter in Cuba
It is also possible to charter a private yacht in Cuba . A few companies offer multi-day trips from the Bay of Cienfuegos to the south of the archipelago on catamarans with up to 16 seats. For more information, check out our sailing trip or contact Cuba Buddy. This is one of the best ways to get to know the great variety of islands in this region of the archipelago with two main destinations:
To the east is the Canarreos archipelago - a group of hundreds of islands of various sizes, where you can find some of the most beautiful and secluded beaches in the Caribbean . Many of these small islands were colonized by pirates during the colonial period, as in the case of Cayo Largo del Sur. It is said that the famous pirate captain Henry Morgan buried the treasures he had stolen after sacking Port-au-Prince in 1666 here. On these small islands with fine white sand beaches and crystal clear waters, you have a good chance of seeing animals such as turtles or dolphins. When visiting the Canarreos archipelago, you can also visit Cayo Blanco del Sur: an island that FIdel Castro gave to the GDR in 1972 and which was renamed after Ernest Thämann, the leader of the German Communist Party.

Charter a catamaran and enjoy your trip!

To the west lies the Jardines de la Reina archipelago - a famous archipelago full of islands and labyrinths of mangroves, making the region an ideal reserve for Caribbean fauna. This area is considered one of the best diving areas in Cuba - especially diving with sharks is one of the main attractions.
Activities on the boat
Marinas Marlin is the Cuban company that controls all tourist activities on the water. In their nautical centers, which are spread throughout the island, they offer many different water sports activities. The wide range of offers allows you to get to know the Cuban seas in many different ways. Below we will present some of our favorites:
• Sail along the coast of Havana. This 3-hour excursion allows you to circumnavigate this beautiful city from the sea. Enjoy the sunset in the bay with a view of the historic Spanish forts that were used to defend the city. This activity is very special because it is the only opportunity for you as a traveler to move on the waters off the capital.
• If you are in Varadero, we recommend the Seafari to Cayo Blanco. A catamaran trip from the famous Varadero peninsula towards the island in question. On the way there you can snorkel and then enjoy the wonderful beach on the cayo.
• In the beautiful city of Cienfuegos, we recommend you take a boat trip around the bay. During this excursion, you will learn about the history of the city and the importance of the bay for its growth. You will also visit several fishing villages and see the Jagua Fortress, which was used to protect the entrance to the bay from enemy attacks. You can also admire the sunset from the boat, which will definitely be an unforgettable experience.
• Cayo Guillermo is one of the most beautiful places in Cuba. It is located in the famous Jardines del Rey and impresses with its wonderful white beaches and the endless mangrove forests full of marine fauna. You can explore this area in a small boat, accompanied by a guide. He will tell you interesting features of the local fauna. He will also take you to the best snorkeling spots with colorful and fascinating underwater world.

Here all you have to do is soak up the sun, feel the warm sea breeze on your skin and enjoy the view of the breathtaking coastline!

• From Cayo Guillermo and Cayo Coco there is a great boat trip to Cayo Media Luna. Sailing through these shallow waters is one of the most incredible boating experiences you can have in Cuba. The water is so shallow and crystal clear that you can see the seabed covered with sand, fish and starfish the whole time. Cayo Media Luna is a small island surrounded by beaches in the middle of the sea. So enchanting that the famous writer Ernest Hemingway was inspired to write his novel "Islands in the Stream". Because of the shallow water you will find several shipwrecks here that invite you to explore with snorkeling or diving. Truly a true tropical paradise!
• From Playa Pesquero or Guardalavaca you can sail to the beautiful Saetía Key. A catamaran will pick you up at the marina of the respective location and take you on a tour of Nipe Bay, one of the largest bays in Cuba. Before you arrive on the island, you have the opportunity to snorkel extensively on the coral reef. At the end of the trip you can spend a few hours on the cayo, which is certainly one of the most beautiful islands in Cuba with its rock formations that merge with the sea and form many hidden beaches.
• The Bahía de Santiago is also one of the most beautiful bays in Cuba and its international nautical base offers many sailing experiences inside and outside the bay. We recommend the snorkeling tour to the Oquendo. One of the ships sank in the Spanish-American War, which ended Spanish rule in Cuba and thus the Spanish Empire. You can watch the sunset from a catamaran at the entrance to the bay - it will certainly be an unforgettable memory of your Cuba trip.
Sailing opportunities with locals
As mentioned above, the laws governing sailing in Cuba are very strict, so if you want something a little more authentic, here are two tips where you can sail surrounded by locals and experience the local culture.
Sailing in Havana
In Havana there is a boat that crosses the bay and connects the old part of the city with the other towns. One of them is Casa Blanca, an old fishing village on the shores of the bay. The Lanchita de Casablanca, as this crossing is called, offers a regular connection every 30 minutes at a cost of 1 Cuban peso. If you want to experience this adventure, you can cross the bay to Casablanca and then go up to El Cristo de La Habana, from where you can enjoy one of the best views of the city.
Sailing in Santiago de Cuba
In Santiago de Cuba there is a similar service that connects the city of Santiago with Cayo Granma. A small island with a great view of the entrance to La Bahía, the San Pedro de la Roca fortress and the city of Santiago. Here you can sit with the residents of the cities to watch the sunset or just experience the daily life of a Cuban. It can be one of the most authentic and beautiful experiences you will have in Cuba.

Our travel suggestions

We are travel specialists for individual trips to Cuba! From vintage car trips, family trips to diving trips, discover our travel suggestions here and ask us about your personal Cuba trip.

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