With a warm climate, friendly and hospitable people, scenic vistas and steady winds, Cuba offers plenty to see and experience. Explore spots along the coastline perfect for sailing, swimming and scuba diving, as well as Cuba's rich culture and history.

Cuba, the largest Caribbean island, is a wonderful place for a sailing adventure, drawing a growing number of visiting yachts each year with its old-world charm, fascinating history and vivacious lifestyle. With a pleasantly warm climate, friendly and hospitable people, many scenic vistas along its coast, and steady winds, the westernmost island in the Greater Antilles archipelago offers plenty to see and experience on a Caribbean cruise. Situated 145 km south of Key West, Florida, Cuba is the third most visited tourist destination in the Caribbean, behind the Dominican Republic and Puerto Rico.

Yacht charter is a popular way of visiting the island, both because sailboats offer a lot of flexibility in planning an itinerary and because the local infrastructure levels and accommodation options still lag behind the enormous demand and finding a place to stay is not always easy. However, Cuba has plenty to offer to visitors, with numerous spots along the coastline perfect for sailing, swimming, scuba diving and various beach activities, as well as a rich musical tradition and many unique cultural peculiarities.

  • Visit Havana and learn to dance the salsa, mambo or rumba, try the famous Copellia ice cream, take a ride through the colourful streets of Habana Viejo in an American classic car from a lost era, and visit the Museo de la Revolución and the Museo Nacional de Bellas Artes
  • Sail to the Canarreos Archipelago to relax on pristine deserted beaches, enjoy the delicious fresh seafood dishes, explore the sparking reefs, and watch the rays in the water and iguanas on the scenic beaches lined with rustic shacks
  • Swim with dolphins and enjoy a Cuban cigar and delicious cocktails while resting in the shade of a palm tree on the majestic Playa Sirena in Cayo Largo del Sur and visit the Cayo Largo Turtle Sanctuary to see baby turtles released to the sea
  • Take a boat trip to the UNESCO-protected city of Trinidad and visit the Topes de Collantes nature park with stunning caves, canyons, grottos, falls, natural pools and the World Heritage Site of Valle de los Ingenios

Cuba enjoys a subtropical climate and has two distinct seasons. The best time to visit is from November to April, when the cooler, dry season provides good sailing conditions with steady trade winds. The weather throughout the rest of the year is mostly rainy, humid and quite hot. The hurricane season lasts from June to November and peaks in late summer. The southern coast of Cuba is more sheltered, with little variation in weather, and offers comfortable sailing conditions for most of the year.

Cuba has about 20 marinas and nautical centers along its coastline. However, visitors can only enter at one of the designated ports of entry. These are Marina Los Morros in Cabo San Antonio, Marina Hemingway in Havana, Marina Gaviota in Varadero and Marina Puerto Vita on the north coast and Marina Santiago in Santiago de Cuba, Marina Cienfuegos in Cienfuegos, and Marina Cayo Largo in Cayo Largo del Sur. Other popular anchorages, including Baracoa, Maria La Gorda and Manzanillo are not ports of entry.

Yacht traffic is quite heavy in the northern marinas, so it is advisable to reserve a berth prior to arrival. The marinas on Cuba’s southern coast are smaller and even more crowded, so chartered boats may need to get on a waiting list before docking. The busiest southern ports are situated in Cienfuegos and Trinidad, where many charter companies have their bases. Marina Hemingway with the National Yacht Club is the island’s largest marina. Situated west of Havana, the marina offers a range of amenities for sailors, including a laundry service, showers, pool and jacuzzi, a small hotel and several restaurants serving Cuban and Spanish cuisine. Havana is only a short taxi ride away.

Sailing itineraries typically take travellers either southeast or southwest of Cienfuegos, the island’s main yachting hub. The south-easterly route, with stops at Trinidad, Cayo Blanco de Casilda and the Jardines de la Reina archipelago, is taken by those looking to explore the country’s culture and history, as well as enjoy the warm tropical sun. The anchorages at Cayo Bréton, Cayo Caballones and Cayo Cuervo are beautiful places to go swimming and snorkelling.

A south-westerly sailing itinerary is ideal for those simply looking to explore the tropical islands and amazing beaches in the Canarreos Archipelago, with popular stops including Cayo Guano del Este, Cayo Largo del Sur, Quinto Canal, Cayo Rosario and Cayo Estopa.

Cuba offers a wealth of cultural delights and a diverse range of attractions and sights to explore. With about 4,000 islets and cays, the country is a scenic blend of stunning sandy beaches, mountains, tobacco fields and colourful old buildings and houses that appear frozen in time. The UNESCO- protected cities of Havana and Trinidad are particularly well known for their impressive architecture and picturesque cityscapes.

Havana is one of the most popular tourist hotspots in the Caribbean. La Habana Vieja, the Old Town, is a World Heritage Site and offers a unique experience of the local street life. Prado, the street that divides the Old Town and Centro Habana, and El Malecón, the city’s waterfront, are the most popular promenades. Havana’s other attractions include the Royal Force Castle, the region’s oldest bastioned fortress, the Havana Cathedral, Fortaleza de San Carlos de la Cabaña, an 18th-century fort, the Partagás Cigar factory, Cámara Oscura, offering 360-degree views of the city, and the superb eastern beaches (Playas del Este). The city’s most popular museums are the Museum of the Revolution, Museo Nacional las Bellas Artes and the Havana Club Rum Museum.

Once known as Al Capone’s favourite vacation spot, Varadero is the place to go for spectacular beaches. The resort town is situated on the Hicacos Peninsula off Cuba’s northern coast. It is home to Tropicana Matanzas, the country’s best-known cabaret, Parque Josone, a landscaped park offering everything from music to camel rides, Delfinario, a popular dolphin show, and the large, impressive Bellamar Caves.

The Jardines del Rey archipelago off Cuba’s north coast includes the popular beach resort islands Cayo Coco and Cayo Guillermo. Cayo Coco is home to Playa Pilar, one of the world’s most stunning white sand beaches.

The historic city of Trinidad, a living showcase of the 17th century colonial Cuba, is situated next to Topes de Collantes, a nature park that harbours the World Heritage Site of Valle de los Ingenios (Valley of the Sugar Mills), a series of three valleys with more than 70 former sugar mills from the
18th and 19th century. Santiago de Cuba, the country’s second largest city and birthplace of the revolutions started by Fidel Castro and Che Guevara, has a picturesque historical center with a vibrant central park accessible by foot. The main attractions just outside the city are the UNESCO-protected San Pedro de la Roca castle and Baconao Park, featuring 200 life-sized dinosaur statues, 2,500 miniature car models, a Taino village and countless other attractions showcasing centuries of Cuba’s natural and political history.

Founded by the French, Cienfuegos offers a slightly different experience than the rest of Cuba. The two main tourist areas are the city center, Pablo Nuevo, and the Punta Gorda peninsula, which harbours many homes from the 1950s. Other attractions include an 18th-century fortress, a lake full
of flamingos, and dolphin shows for kids.

The Canarreos Archipelago is one of the most popular destinations in Cuba. Consisting of about 350 islets, the archipelago offers a quieter, more rustic ambience than other sailing destinations in the country. The islands are perfect for snorkelling, relaxing on the beach, watching a colourful variety of fish and trying some of the world’s most delicious seafood dishes. The most popular destinations in the archipelago are Cayo Largo del Sur and Isla de la Juventud.

Cayo Largo del Sur has a strong, well-developed tourist infrastructure and is home to Playa Sirena, a spectacular 2 km long beach with calm waters and plenty of natural shade under palm trees. Located near the marina, the Cayo Largo Turtle Sanctuary offers visitors a unique opportunity to see turtles nesting and watch baby turtles as they are released into the sea.

Home to the endangered Cuban crocodile, Isla de la Juventud is very popular with beach goers and divers. The island is known as the site of many battles in the 16th and 17 centuries and its coves and caves are the birthplace of many pirate legends. Far less developed than other destinations in the country, the island is perfect for those looking for a remote, sheltered getaway spot as an alternative to resort-heavy tourist hotspots along Cuba’s coast.

+ Boat listings

Check In

Check Out


Boat Type

Producer & Model

Equipment & Extras

Price ANY

Year ALL

Sort by

Length ALL

People ANY

Cabins ANY

Show availability:

More results