Cuba is synonymous with political intrigue — from the Cold War and the Bay of Pigs invasion to Fidel Castro and the Cuban Revolution. Now you can explore Cuba’s history and its shape-shifting relationship with the world on Vantage’s Cuba 360°: A Circumnavigation of the Cultures of Cuba. This adventure aboard the mv Victory I takes you directly from Key West to Havana, where music, art deco, and classic cars will transport you to the 1950s. You’ll explore the ruins of Trinidad’s sugar industry, tour the historic Bay of Pigs, and visit the Moncada Barracks in Santiago de Cuba — the very site that launched the Cuban Revolution. Of course, no journey to Cuba is complete without enriching People-to-People exchanges, one-of-a-kind forays into an electrifying arts scene, and a legendary performance by Buena Vista Social Club.
Smell the sea air and spicy cigars on this unforgettable journey through Cuba’s colonial and contemporary history. But act quick to reserve your spot — these departures are limited!
Fly to Miami and begin your Cuban adventure
Welcome to Miami! Tonight your Cuban adventure begins when you embark the ms Victory I and cast off for Key West, enjoying an orienting and informative Welcome Reception along the way.
Key West trolley tour, San Carlos Institute, free time to explore
Glamour meets rusticity today when you enter Key West, the southernmost city in the contiguous United States. Discover this paradisiacal island on a trolley tour that brings you to historic Old Town, home to Mallory Square, the island’s foremost waterfront district where street performers, locals, and sunset lovers gather nightly for a sherbet-colored show over the Gulf of Mexico. You’ll also visit Duval Street, lined with salt-worn pubs, cafés, galleries, and a true taste of authentic Key West flavor. Speaking of flavor . . . you’ll enjoy lunch at a local restaurant, during which you can sample a few local delicacies, including conch fritters and key lime pie.
Next, get an early taste of Cuba with a walking tour to the San Carlos Institute. Founded by Cuban exiles, this museum, gallery, library, theater, and school is a repository of Cuban history and culture, and a perfect introduction to what’s in store as we set off for Cuba this evening.
But first, enjoy free time to explore Key West on your own. Perhaps you’ll visit the French-colonial Ernest Hemingway House — currently the permanent home to several six- and seven-toed cats famously descended from Hemingway’s own pets — or the Truman Little White House. Once a getaway for several U.S. presidents, the building became the official wintertime White House for President Harry S. Truman, who conducted business and met with world leaders here over 11 visits totaling 175 days.
Exploring the cultural hotbed of Havana, Hemingway’s island retreat, and a Buena Vista Social Club show
Here we are at the epicenter of Cuban life and culture in the extraordinary city of Havana. As we near Havana’s harbor, look for the dramatic El Morro fortress guarding the harbor entrance. Unforgettable Moment: An exploration of Habana Vieja (Old Havana) brings us to the four main colonial-era squares, including the exquisitely restored Plaza de Armas and the Plaza de Catedral, with its asymmetrical cathedral constructed in the 1700s. As you explore, note the changes underway in Havana, including the restoration of long-neglected colonial façades and the opening of bright new shops and restaurants. Cultural Discovery: A series of exciting People-to-People visits brings Cuban art and culture into the fore. First we’ll tour an arts studio before lunch at a local paladar, then step back in time with a ride in some classic American cars.
Unforgettable Moment / Cultural Discovery: Wheeling through town in these stylish vintage vehicles, 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: We’ll return to ship to freshen up for dinner and an exclusive evening performance of the world-renowned Buena Vista Social Club. This iconic ensemble will revive the music of pre-revolutionary Cuba inside Havana Café.
Enjoy the Caribbean breeze with a day at sea
Enjoy your time aboard the mv Victory I as we make our way toward Trinidad through stunning turquoise waters. Our days are sure to be filled with ideal weather, so take this opportunity to enjoy some downtime — perhaps relaxing on the ship’s observation and sun decks, watching spectacular Caribbean views unfold.
Enjoy another day at sea as we near Trinidad. Enjoy a treatment inside your onboard salon and spa, cozy up with some mojitos on the observation deck, or soak up the sun on the outdoor lounge chairs. Historical and cultural talks with our onboard expert Cuban lecturers will enhance your experiences on land.
Trinidad’s local color, sugar history, and vibrant artistic life
Discover the magic of colorful Trinidad and its sobering Valley of the Sugar Mills, a living museum of the once-bustling sugar industry that prompted UNESCO to name this region a World Heritage Site. Smell the whiff of Cuban cigars on a walking tour of Old Trinidad, where you’ll discover rows of Spanish colonial buildings, including Plaza Mayor, the heart of the city, as well as its cobblestoned streets, horse-drawn carts, and the jangling echo of music, which is never far away in Cuba. Cultural Discovery: Before lunch at a local paladar, meet a local artist on a special People-to-People visit that sheds light on how working artists flourish in and are inspired by this region.
We’ll then explore the ruins of San Isidro de Los Destiladeros. Once a humming sugar mill, this now-defunct hacienda is an essential stop for understanding Cuban history, beginning with the thousands of Spanish-imported African slaves who lived here in squalid conditions and propelled the sugar industry to global prominence at a staggering human cost. You’ll see how vast an empire the sugar industry once was when we pause for photos at a “mirador” overlooking the Valley of the Sugar Mills, a series of three interlocking towns home to 75 former sugarcane mills.
Cultural Discovery: Next, meet a member of one of Trinidad’s most artistic families. Since Modesto Santander learned pottery from a Spanish immigrant in the 19th century, the Santander family has been synonymous with the clay pottery of this region. On another enlightening People-to-People visit, you’ll visit the Santander studios and learn how the family trade has been passed down through generations.
Cuban history in a cup at a coffee plantation
This morning, we’ll ascend by coach to Topes de Collantes, a nature reserve in the Escambray Mountains. We’ll scope out these lush rainforests, which are home to more than 40 orchid species and Cuba’s national flower, the mariposa, or butterfly lily. More than 40 varieties of coffee also grow here, and we’ll next visit a nearby working coffee plantation in yet another People-to-People visit that showcases the history — and flavor — of this tasty Cuban staple.
Cultural Discovery: As you’ve probably already realized, traditional Cuban coffee is nothing like the stuff you brew back home each morning. For one, Cuban coffee is smaller but packs a mightier wallop; that’s because it’s really espresso that’s been topped off with foam made from coffee whipped with sugar. Known as cafecito — that’s “little coffee” in Spanish — this Cuban brew is a tiny representation of a nation that has constantly made do with very little.
Discovering the architecture and art of Cienfuegos
Wake up today in Punta Gorda, a mansion-lined peninsula in Cienfuegos, Cuba’s “Pearl of the South.” On a morning walking tour, discover this UNESCO World Heritage Site’s colorful architecture, lively farmers’ markets, and Cienfuegos Boulevard, the city’s main thoroughfare dotted with monuments and storefronts. The architecture here may remind you of New Orleans, and for good reason — French immigrants from Bordeaux and Louisiana settled this city in the 19th century.
Cultural Discoveries: Before lunch on board, some free time will bring you to several artist studios and galleries. Later, another People-to-People encounter will introduce us to the Writers and Artists Union of Cuba (UNEAC) and its role in preserving and promoting Cuban arts. You’ll also get a unique insider's look at the local art scene when we visit the workshop of renowned engraver Rafael Cáceres.
Historical Bay of Pigs drama, exclusive Cienfuegos Orchestra performance
To the west of Cienfuegos lies the infamous Bay of Pigs, site of the failed U.S. military invasion to topple Fidel Castro. Today, the bay is home to craggy blonde beaches, seafood shanties, and a coral reef that belies the intense events that took place here in 1961. During a guided visit to the Girón Museum, we’ll learn more about this historic conflict and how it went awry. Cultural Discoveries: Tonight, we’ll experience more local Cuban culture when we attend an exclusive performance by the Cienfuegos Orchestra.
Enjoy another day at sea as we cruise to Santiago de Cuba. Maybe you’ll sit down for a traditional afternoon tea service, or enjoy the sun and tropical Caribbean views from a relaxing spot on the sun deck.
Santería in Santiago, and a visit to the site that launched a revolution
Home of legendary rum and birthplace of the revolution, Santiago de Cuba has soul. Most of Santiago’s population is descended directly from Haitian and African slaves brought in the 18th century to man sugar plantations. Today, Cuba’s second-largest city is more like Havana’s little sister, a spunky outlier and cultural capital that bestowed the world with the musical genre son, from which salsa derived. There’s an undisputable magic here, and it’s not just the Santería practiced by many of Santiago’s denizens, but an infectious vitality evident in the city’s numerous bars and clubs, rife with live music.
Cultural Discoveries: Another memorable People-to-People experience brings us to Casa del Caribe — two former mansions converted into a cultural research institute — to learn about Afro-Cuban culture and the island’s popular religion of Santería. Meet local practitioners and even get a divination reading from one of the local espiritistas but, either way, dispel your notions about what you think you may know about this religion — the truth will surprise you.
Afterward, we’ll head to the unlikely spot where the Cuban Revolution launched — the Moncada Barracks. Here, Castro led a group of 135 rebels to Batista’s second-largest military garrison in an attack ridden with snafus — and death on both sides. Unforgettable Moment: We’ll hear the story behind the attack before visiting the 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. After our guided tour, we’ll have lunch at a local restaurant.
Then it’s on to the home of Conquistador Diego Velazquez de Cuéllar, who established Santiago in 1515, as well as the grand Cathedral of Santiago and Parque Céspedes. The city’s main square is a haven for vibrant, musical street life and the perfect way to cap off your first afternoon in Santiago.
History inside Sanfa Ifgenia Cemetery, Santiago’s arts scene
A second day in Santiago unveils even more surprises and fabulous People-to-People exchanges. Over at the Santa Ifigenia Cemetery, see the formidable mausoleum where Cuban poet, essayist, and revolutionary José Martí is buried right next to 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.
Next, we’ll head over to the Complejo Cultural Meneses, a local arts organization that hosts the annual Festival del Caribe, a weeklong bash featuring music, dance, and outrageous costume. Cultural Discovery: Afterward, we’ll take in an exclusive performance by Cutumba, a local folklórico dance and percussion group. After lunch on board, enjoy leisure time to explore Santiago on your own.
A day at sea
Our Cuban adventure winds down with two days of tropical cruising as we skirt Cuba’s northern coast, bound for Miami. Watch as the mountains along the eastern end of the island gradually give way to verdant hills and coffee plantations.
Enjoy a final day at sea
Take this final day at sea to soak up some Caribbean sun, enjoy classic Cuban fare in the mv Victory I’s restaurants, chat with friends you’ve made along the way, and simply enjoy the breeze.
After breakfast on board, you’ll disembark in Miami and transfer to the airport for your return flight home.
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.