Fly from Miami to Cuba, then transfer through the countryside to Santiago de Cuba
Today we fly from Miami to Holguín, then transfer to Santiago de Cuba just in time for a Welcome Dinner at the hotel. Fidel Castro and his fellows in arms launched their revolution from Santiago, making this historic city tucked between the Sierra Maestra mountains and an enclosed bay a fitting place to begin your journey across Cuba.
Please note: Arrive to your destination or home rested and refreshed! Convenient gateway city stopover options mean you can break up longer flights easily — just ask our Flight Experts for assistance.
Explore historic Santiago by day, then dance the night away at the Casa de la Trova music hall
Santiago de Cuba was one of the first European settlements in Cuba, dating to 1514. It’s also where Fidel Castro and his fellows-in-arms launched the revolution, making this scenic city tucked between the Sierra Maestra mountains and a protected bay a fitting place to begin your journey.
Today’s tour of the historic district includes the house of the city’s founder, Diego Velázquez. You’ll also visit the peaceful Santa Ifigenia Cemetery, where Cuban poet, essayist, and revolutionary José Martí is buried in a fortress-like mausoleum.
Following lunch in a local restaurant, visit the Morro Castle, the daunting Spanish fortress also known as Santa Pedro de la Roca that was built to repel invaders at the bay’s narrow entrance. Cultural Discovery: After dinner on your own, it's time to put on your dancing shoes! Cuba’s hottest musicians will have you up on your feet as we head for the famed Casa de la Trova nightclub. Although music is everywhere in Cuba, Santiago’s squares, clubs, and performance halls are renowned for having given rise to many of Cuba’s most famous musical styles and musicians.
Visit El Cobre shrine, tour Bayamo by horse and buggy, then arrive at our Holguin beach resort
Departing on the first overland leg of our cultural journey, we soon arrive in the old copper mining town of El Cobre. Cubans of all walks of life make the pilgrimage here to pray at the tiny but ornate statue dedicated to Cuba’s patron saint, Our Lady of Charity of El Cobre. Among the gifts left at the sanctuary is Hemingway’s gold Nobel Prize for Literature, which he dedicated to the Cuban people. Continue through the mountains to Bayamo, a sugar plantation town that witnessed some of the earliest uprisings against Spanish colonial powers. Cultural Discovery: Enjoy lunch in a local restaurant, then tour Bayamo’s nicely restored historic district in a horse carriage. From there, we continue on to our Deluxe all-inclusive resort in Holguín, where we'll have time to enjoy the beach.
Exploring Holguin, paper factory visit, and Neon Theater performance
Your city tour begins with an overview of the city and the sea from the Loma de la Cruz overlook. Then, admire Holguín’s three colonial plazas as we explore this pleasant city. Cultural Discoveries: Visit a fascinating paper factory that makes handmade paper and uses traditional letterpress equipment to produce books and other material that are themselves works of art. You’ll also attend an amazing performance under blacklight at the innovative Neon Theater. Enjoy the rest of the day at leisure at your all-inclusive beach resort.
Explore the squares of Camaguey by bike taxi, then visit local artists’ studios
A morning drive takes us to Camaguey. It’s said that the twists and turns of the labyrinthine old city center — now a UNESCO World Heritage Site — were built that way to confuse pirates. You’ll get a unique view of the old city on a tour by bici-taxi, the bicycle-powered rickshaws used for local transport. During your tour, take note of large red clay pots on doorsteps — called tinajones, they’re a symbol of the city. We’ll also stop to visit several artists in their studios. Enjoy lunch in a restaurant overlooking one of the historic squares, then enjoy free time to start exploring.
Ballet company rehearsal, Cuban cowboy encounter at Rancho King, and rural school visit
Cultural Discovery: Start the day by dropping in on a rehearsal of En Dedans Ballet Company, a troupe internationally known for its unique blend of classical and contemporary dance.
Afterwards, we visit Rancho King, the Cuban outpost of the legendary King Ranch of Texas. Enjoy lunch in the ranch dining room, tour the grounds in a horse-drawn cart, and watch skilled vaqueros perform a roping demonstration. Cultural Discoveries: You’ll also have a chance to meet some of these Cuban cowboys, many from families that have worked the ranch for generations. In addition, we’ll visit a rural community and have the opportunity to learn about rural life in this part of Cuba. You’ll have the remainder of the afternoon and evening at leisure in Camaguey.
Discover the UNESCO city of Trinidad, then ride to bayside Cienfuegos
First stop today, as we continue to make our way up the island, is a meticulously well-preserved colonial city nestled among green hills. With its UNESCO designation and cobblestone streets, stately palaces, and trim plazas, Trinidad is often referred to as the “museum city of Cuba.” Unforgettable Moment: On a walking tour, admire the fine colonial buildings as you make your way to the charming main square for a peek inside the cathedral. You’ll also visit the studios of artists and craftspeople that find inspiration in Trinidad’s lost-in-time atmosphere. Afterwards, we’ll proceed to Cienfuegos, another picturesque city with a fascinating history.
Historic Remedios and Sugar Museum, Che Guevara Mausoleum, and more
Discover another colonial gem, the charming town of Remedios, which was founded early in the 15th-century. Cultural Discovery: Board a vintage train pulled by a steam locomotive for a ride to the Sugar Museum, where open-air exhibits showcase the process once used to refine “white gold” from the sugarcane grown in vast plantations. Enjoy lunch in a local restaurant, then continue to Santa Clara to visit the mausoleum dedicated to Che Guevara. In 1958, Santa Clara was the site of the decisive battle of the revolution, when Che-led troops ousted government forces. The revolutionary hero was reinterred at the mausoleum in 1997 after his remains were recovered from a mass grave in Bolivia, where he was executed while helping lead an uprising there. You’ll have the evening free in Cienfuegos.
Tour the UNESCO city of Cienfuegos, then transfer overland to Havana
Enjoy a walking tour of Cienfuegos' graceful Old Town, which has been designated a UNESCO World Heritage Site for it’s French neoclassical architecture and 19th-century city planning. During your visit, you’ll see the Tomás Terry Theatre, the Government House, and the Catedral de la Purísima Concepción. Then it’s on to Havana, where you can settle into your Deluxe hotel, located in one of the most elegant areas of New Havana, just steps from the famous malecón seafront boulevard.
Sister Teresa Vaz daycare center visit, exploring Havana Vieja, and arts and crafts visits
Enjoy a morning at leisure today. Vantage Cares: Visit the Sister Teresa Vaz center, our Vantage Cares site in Cuba. The dedicated staff provides day care and other services to the underserved youth of Havana. In addition to supporting the day care center, Vantage provides uniforms for the center's thriving youth soccer program. Afterwards, explore Habana Vieja (Old Havana) on a walking tour that takes you among the four main squares dating from the colonial era, including the beautifully restored Plaza de Armas and the Plaza de la Catedral, with its gem of a cathedral. You’ll also be able to see for yourself the changes taking place in Havana, from the restoration of colonial façades to the opening of shiny new shops and restaurants. Cultural Discoveries: We’ll drop into a silk-screening studio, where you can meet the artists. Afterwards, enjoy lunch at a noted Havana paladar, a restaurant in a family home. We’ll also stop in Havana’s famed arts and crafts market — it’s the perfect place to pick up last-minute gifts.
Examining Cuban healthcare, historic Colón Cemetery, and legendary Hotel Nacional tour
Cultural Discoveries: Despite the very modest living standard of most islanders, Cuba is renowned for its excellent medical care. Visit a local clinic to see how the dedicated staff provide healthcare on a daily basis. We’ll also visit the historic Colón Cemetery, where elaborate mausoleums create a city of the dead. Look for monuments dedicated to famous Cuban baseball teams, and the soaring memorial to firefighters who perished in the great fire of 1890. Afterwards, providing the counterpoint to the beginning of your Cuban adventure, you’ll view Havana’s great El Morro fortress, built by the Spanish to protects the city from its cliff-top perch.
In the afternoon, we’ll tour the Hotel Nacional de Cuba, an icon from the “Rat Pack” era and once the most glamorous destination in the Caribbean. Stopping into the bar for a cocktail, we’ll see photos of the personalities, from movie stars to mobsters, who once frequented the Nacional.
Visit a cigar factory, see Hemingway’s home, explore the Fusterlandia art zone, and ride a vintage “Yank tank” to our Farewell Dinner
Cultural Discovery: Stop by a cigar factory in the morning, where you’ll learn about this most iconic of Cuban products. Afterwards, visit Finca Vigía, Ernest Hemingway’s beloved island retreat. He worked on some of his most famous novels here, including The Old Man and the Sea and For Whom the Bell Tolls. The Nobel Prize-winner loved Cuba and the feeling was mutual — he’s considered national hero to this day. Cultural Discovery: A different sort of artist becomes the focus of our next visit, as we view the mind-boggling ceramic and sculptural artwork of José Fuster, who transformed an entire neighborhood into a vivid alternative reality known as “Fusterlandia.” You’ll have the remainder of the day free, perhaps to do some last-minute souvenir shopping in Habana Vieja.
Unforgettable Moment: We’ll gather once again in preparation for a Farewell Dinner that begins with a ride in a vintage American car. Before the 1962 embargo, Chevies, Fords, Dodges, and other classics from the 1950s prevailed on the island nation. Ingenious Cuban mechanics have kept many of these "Yank tanks” in meticulous running order in the decades since. Today, they are one of the most distinctive sights on a vibrant island that often seems frozen in time. But as you raise a glass in farewell to our fellow travelers and the Cuban people, you can count yourself lucky to have visited this island nation people before it changes forever.
Depart Havana and fly home
Transfer to Havana's international airport for your return flight to the U.S.
Important Notice: The above day-by-day itineraries are preliminary and therefore subject to change. If changes occur while on tour, you will be notified by your Vantage Adventure Leader or regional expert.
Please Note: The hotels listed are preliminary and subject to change. Although we contract our hotels a year in advance, unforeseen situations do occasionally occur. Should it be necessary to change a hotel, one of equal quality and value will be substituted. You will receive verified hotel information with your final itinerary. That hotel ratings are based on the Hotel and a leading travel industry authority on hotels throughout the world.