Arrive in Havana, the colonial capital of Cuba. With its beautiful balconies, wrought iron railings, and idyllic inner courtyards, a stroll through Old Havana, a UNESCO World Heritage Site, brings you right to the heart of life in the city. Old American limousines cruise past magnificent colonial buildings on the wide boulevards and the Malecón Promenade is a popular place to walk at sunset. In the legendary Tropicana club, where stars like Frank Sinatra and Josephine Baker once appeared on stage, the flamboyant, high-spirited shows still create the same mood today as they did when it opened in 1939.

On day 2, enjoy a tour of the old town before boarding your ship, the Sea Cloud. Settle in to your cabin as the ship sets sail.

Enjoy the ship's luxurious amenities as she sails for the Isla de la Juventud, Cuba.

The "Isle of Youth" is the largest of Cuba's lesser islands. It was a refuge for notorious privateers like Sir Francis Drake and Henry Morgan, and is said to have been the inspiration behind Robert Louis Stevenson's famous novel, "Treasure Island". Nowadays, you can treat yourself to some sun here and let the Caribbean waves wash round you. The beaches are almost untouched and are still a well-kept secret. The treasures in the sea around the island were designated as a nature and marine reserve in 1980.

Visit Cayo Largo del Sur, a small resort island in Cuba, off the south coast of the northwestern part of the main island in the Caribbean Sea. The cay is about 25 kilometers (16 mi) long and 3 kilometers (1.9 mi) wide and is the second largest island in the Canarreos Archipelago. 

Cienfuegos, a UNESCO World Heritage Site since 2005, is known as the Pearl of the South. The city owes its grand, romantic architecture to the French colonists who first settled there. The beautiful old town of Trinidad de Cuba is a true gem, with lovingly restored colonial facades, sleepy lanes, and a turquoise sea. This friendly town has an important past as the center of sugar cane cultivation. Experience its charming coastal setting, lovingly restored facades, and gentle pace of life in any of the town’s beautiful squares and old, narrow streets. This small town has a well-deserved place on the UNESCO World Heritage Site list.

Enjoy Playa Ancón, a precious ribbon of white beach on Sancti Spíritus' iridescent Caribbean shoreline. It is usually touted – with good reason – as the finest arc of sand on Cubas's south coast. An optional excursion to Trinidad is offered.

Enjoy this day offshore, relaxing and taking in the smell of the fresh ocean breeze up on deck.

The El Morro fortress towers high above the bay and was almost completely destroyed by the pirate Henry Morgan. Santiago de Cuba, an architectural gem, is proud not only of its reputation as the birthplace of the revolution, but also of its musicality. If you go for a walk, sooner or later you find yourself in an authentic Salsa bar. The whole city has music in its blood, and nowhere else do people make so much music or dance so much. The rhythms of the Salsa, Son and Rumba are just as thrilling in clubs, bars and schools as they are in the famous Buena Vista Social Club. 

Port Antonio was once the world's banana capital. The pretty little town, surrounded by sugar cane fields and banana plantations, impresses travelers with its delightful beaches. The Rio Grande, on which you can take a boat tour, is the island's largest river and channels its course over 37 miles of green solitude through the jungle and into the sea. Historically, bananas and other fruit were carefully transported on bamboo rafts along the waterway to the port. Nowadays, the rafts have been equipped with bench seats and are used for excursions. 

Enjoy the ship's luxurious amenities as she sails for the Dominican Republic.

During the sugar boom of the late 19th century, La Romana developed into a lively working-class city and eastern sugar center. The third largest city in the Dominican Republic now has many faces. The streets are laid out in a grid formation with colorfully painted houses. Between these and the golf courses and luxury villas of the prominent Casa de Campo flows the Rio Dulce, which runs into the sea. Native Taino art plays a large role, both in the city's archaeological museum and in what is perhaps the country's most beautiful cave, Maravillas. This was a cult site for the native Taino people and lies 35 meters below ground. The numerous cave paintings are more than 1,000 years old and have been exceptionally well preserved.

Arrive in Santo Domingo in the morning and disembark after breakfast. On this island, which is part of Hispaniola, Columbus founded the first Spanish colony in America. Santo Domingo, the present capital of the Dominican Republic, is the first and oldest European-founded city in the New World. "Old" in the New World still means relatively young - it corresponds to Renaissance visions of the ideal and was the model for many cities in Latin America. A visit to the historic old city is like a journey through time. The splendid stone buildings are testament to the era of the colonial conquests and have been designated as World Heritage Sites under the protection of UNESCO.