Fly to Cuba, transferring through the countryside to Santiago de Cuba
You’ll fly from Miami to Holguín, and then transfer to Santiago de Cuba just in time for a Welcome Dinner at the hotel. Fidel Castro and his comrades-in-arms launched their revolution from Santiago, making this historic city a fitting locale to begin your journey across Cuba.
Please note: Arrive to your destination 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
Explore Santiago de Cuba today. One of the first European settlements, Cuba’s second-largest city is today home to legendary rum and music, as well as a revolutionary history.
Embark on a tour of the historic district that includes the home of Conquistador Diego Velazquez de Cuéllar, who established Santiago in 1515. You’ll also visit the Santa Ifigenia Cemetery, where Cuban poet, essayist, and revolutionary Jose Martí is buried beside a more familiar name — Fidel Castro. Before he ignited a revolution and rose to prominence as Cuba’s fiery prime minister, he was a misbehaved schoolboy in Santiago.
Following lunch in a local restaurant, visit citadel of San Pedro de la Roca, known locally as El Morro (Spanish for "fortress"), which was named a UNESCO World Heritage site as the most complete and best-preserved example of Spanish-American military architecture. 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 birthing many of Cuba’s most famous musical styles and musicians.
Visit El Cobre shrine, tour Bayamo by horse and buggy, then arrive at our Holguín beach resort
Departing on the first overland leg of our cultural journey, you’ll 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 the country’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, home to the ruins of the region’s once-thriving sugar plantations. Cultural Discovery: Enjoy lunch in a local restaurant, then tour Bayamo’s historic district in a horse-drawn carriage. From there, continue on to your deluxe resort in Holguín, where you’ll have time to enjoy the town’s blonde beaches.
Exploring Holguín, paper factory visit, and Neon Theater performance
Take in the sweeping expanse of Holguín and the surrounding sea from Loma de la Cruz — Hill of the Cross — on a city tour. Cultural Discoveries: At a working paper factory, see how traditional letterpress equipment is used to produce books and other materials that are nothing short of artworks. You’ll also attend an illuminating performance by the Neon Theater, which uses both puppets and black light to weave an innovative and unforgettable show. Enjoy the rest of the day at leisure at your deluxe beach resort.
Explore the squares of Camaguey by bike taxi, then visit local artists’ studios
A morning drive takes us to Camaguey, where the labyrinthine streets of this historic city center — now a UNESCO World Heritage Site — were built 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 ride along, take note of the tinajones — large red clay pots on doorsteps, which have become a symbol of this 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 for 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 that’s internationally lauded for its unique blend of classical and contemporary dance.
Afterwards, visit Rancho King, the Cuban outpost of the legendary King Ranch of Texas. Enjoy a rustic farmer’s 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 of whom hail from families that have worked the ranch for generations. In addition, we’ll visit a rural community and learn more about the country 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
Discover Trinidad, the “Museum City of Cuba” today. This meticulously preserved colonial city rightfully earned its UNESCO designation with cobblestone streets, stately palaces, and palm-studded plazas. Unforgettable Moment: On a walking tour, admire the town’s colorful colonial architecture as you make your way to the charming Plaza Mayor for a peek inside the cathedral. You’ll also visit the studios of artists inspired by Trinidad’s timeless 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 more colonial gems in Remedios. With its 15th-century founding, the town is rumored to be the second-oldest settlement on the island. Cultural Discovery: Board a vintage train for a ride to the Sugar Museum, where open-air exhibits showcase the history of slavery and machinery at these one-time 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 became the site of the revolution’s decisive battle after Guevara-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. Enjoy dinner at your hotel tonight.
Tour the UNESCO city of Cienfuegos, then transfer overland to Havana
Head out on a walking tour of Cienfuegos, Cuba’s so-called “Pearl of the South.” A seductive cove protected by its own bay, Cienfuegos is also a UNESCO World Heritage Site thanks to its unique architecture evocative of a more tropical Paris — a side effect of its 19th-century settlement by French immigrants. During your visit, you’ll see the Tomás Terry Theatre, 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 day-care center visit, exploring Havana Vieja, and arts and crafts visits
This morning, enjoy an overview of the city from San Felipe Castle, the fortress built to protect Havana from sea raiders. 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 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 and 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 — 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. A visit to a local clinic sheds light on how the staff provide healthcare on a daily basis. We’ll also stop by 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, you’ll view the El Morro fortress, which guards Havana’s harbor.
In the afternoon, we’ll tour the Hotel Nacional de Cuba, an icon from the “Rat Pack” era and once the Caribean’s most glamorous destination. Stopping into the bar for a cocktail, we’ll see photos of the personalities — from movie stars to mobsters — who once frequented the Nacional. Enjoy an evening at leisure.
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 the most iconic of Cuban products. Afterwards, we’ll make our way to Finca Vigía, Ernest Hemingway’s beloved island retreat of over 30 years. This figurehead of American literature wrote two of his most celebrated novels — For Whom the Bell Tolls and The Old Man and the Sea — right here, becoming a hero amongst Cubans for residing in working-class San Francisco de Paula. 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 working order in the decades since. Today, they’re 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.
Please note: Arrive home rested and refreshed! Convenient gateway city stopover options mean you can break up longer flights easily — just ask our Flight Experts for assistance.
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. The hotel ratings are based on the hotel and a leading travel industry authority on hotels throughout the world.