Learn more about our Travel Heath Advisory Update and 2020 Oberammergau.

Across Cuba: From Santiago de Cuba to Havana - 2020

Miami • Santiago de Cuba • Holguín • Camaguey • Trinidad • Cienfuegos • Havana
Save up to 10%
The earlier you reserve, the more you can save with SmartPay!SM
Leader in Solo Travel
FREE Single Supplements on every departure, limited availability — reserve now!
The earlier you reserve, the more you can save with SmartPay!
After decades of stasis, Cuba is still basking in the tropical limelight on the international stage. Travel with Vantage on an exhilarating land tour of this storied island nation — now with added dates to accommodate popular demand and new travel guidelines! — and experience a Cuban revelation of cultural, natural, and historical glory as you journey the length of the country from Santiago to Havana. Along the way, you’ll feel the rhythm of Cuban life during performances by musicians, dancers, and theater groups; trace the pungent waft of world-famous cigars to colonial city squares and neoclassical marvels; and engage with cowboys, locals, and artisans in unforgettable support exchanges. Explore the soul of Santiago, support and interact with local Cubans in their parks and markets, and meander the maze of Camaguey’s UNESCO-listed lanes before unveiling Trinidad’s charms, trekking Cienfuegos’ Old Town, and spending a remarkable four nights in Cuba’s indisputable epicenter — Havana.

From its timeworn flourishes to Hemingway’s legacy, Havana has enraptured imaginations for decades. There, you’ll visit underserved youth at day-care center, explore Hemingway’s beloved island retreat, and soak in the local color of Habana Vieja. With its cocktail of relics, revitalization, and — yes — rum, Cuba is as intoxicating as ever.

What memories will you bring home on this adventure? Check out our photography page for inspiration, tips and tricks, and more. Explore now!

Santiago de Cuba to Havana

Close All

DAY 1:

Fly to Miami for an overnight

Begin your thrilling adventure with a flight to Miami. Upon arrival, you’ll board a free shuttle to your hotel, located nearby for utmost convenience. We've arranged a chartered morning flight to Holguín to comply with new Cuba flight regulations — however, we're still more than welcome to visit and explore this vibrant country! Feel free to ask your Adventure Leader for some great restaurant recommendations in Miami if you'd like a night out on the town.

DAY 2:

Fly to Cuba, transferring through the countryside to Santiago de Cuba

In the early morning, you’ll take a shuttle to the airport and have a chartered flight from Miami to Holguín. Then, we'll transfer to Santiago de Cuba and stop along the way for a snack at a local farm and interact with the locals. It's a wonderful way to begin your journey into Cuba and support the Cuban people while enhancing your understanding of Cuban culture. In the evening, celebrate your arrival with a Welcome Dinner at the hotel.

Included Meals:

Breakfast & Dinner

DAY 3:

Explore historic Santiago by day, including Parque Cespedes, 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. 

You’ll also get a chance have more meaningful interactions with during a walking tour of Parque Céspedes, which is one of Santiago’s most important political and religious sites.

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, where you’ll have a chance to meet and chat with the band. 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.

Included Meals:

Breakfast  & Lunch

DAY 4:

Visit El Cobre shrine, tour Bayamo by horse and buggy and experience the everyday lives of Cubans, then arrive at your Holguín 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: Here, you’ll enjoy lunch in a private restaurant, before continuing your support of Cuba’s private business sector on an exploration of Bayamo’s historic district by horse-drawn carriage. You’ll make stops throughout town and have plenty of opportunities to meet and interact with locals — this truly is an authentic way to experience the everyday lives of Cubans! From Bayamo, you’ll continue on to your deluxe resort in Holguín.

Please note: On 1/11, 01/25, 02/29, 03/28 and 08/29 departures, travelers will stay at the Iberostar Holguin instead of the Paradisus de Oro.

Included Meals:

Breakfast, Lunch & Dinner

DAY 5:

Exploring Holguin, 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, meet and greet local artists who will demonstrate 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. You’ll also learn how the initiative helps local children learn about the arts, music, and more.

Enjoy the rest of the day at leisure at your deluxe beach resort. Tonight, support the local economy during a visit to another paladar. These family-run restaurants are everywhere in Cuba, and a delicious way to learn about local life and cuisine.

Please note: On 1/11, 01/25, 02/29, 03/28 and 08/29 departures, travelers will stay at the Iberostar Holguin instead of the Paradisus de Oro.

Included Meals:

Breakfast, Lunch & Dinner

DAY 6:

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. You’ll have the opportunity to hop on and off your bici-taxi, in case you want to engage local vendors and purchase fruit or other handcrafted souvenirs. During your tour, also 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.

Included Meals:

Breakfast  & Lunch

DAY 7:

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.

Included Meals:

Breakfast  & Lunch

DAY 8:

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.

Included Meals:

Breakfast, Lunch & Dinner

DAY 9:

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. Tonight’s dinner brings us to another local paladar for another taste of authentic Cuban home cooking.

Included Meals:

Breakfast, Lunch & Dinner

DAY 10:

Tour the UNESCO city of Cienfuegos, then transfer overland to Havana and visit the Mercado Agropecuario

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. Cultural Discovery: In Havana, we’ll set out on a visit to the Mercado Agropecuario, where locals come to purchase their weekly groceries. Here, you’ll have the chance to interact with local vendors, sample some foods, and ask questions about traditional Cuban ingredients.

Included Meals:

Breakfast  & Lunch

DAY 11:

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.

Included Meals:

Breakfast  & Lunch

DAY 12:

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. 

Lunch is at a local paladar, where you’ll participate in a hands-on cooking demo and have the chance to learn about local foods from a local. This is a great way to see how the ingredients you viewed and sampled in the Mercado Agropecuario are put to use!

Afterward, visit the studio of Kadir Lopez, a local artist who restores vintage neon signage as part of his Havana Lights Project. The project is a provocative way to force Cubans to look up and notice the restored signs and forgotten architecture.

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.

Included Meals:

Breakfast  & Lunch

DAY 13:

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.

Included Meals:

Breakfast, Lunch & Dinner

DAY 14:

Depart Havana and fly home

Transfer to Havana’s international airport for your return flight to the U.S.

Included Meals:


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.

Meet Your Vantage Team

Contact Vantage

CALL 1-800-848-5773

View Journey Map

Be prepared for
your journey with
our Adventures
get your gear

Across Cuba: From Santiago de Cuba to Havana - 2020

Call us to reserve your next vacation:

Earn up to $1,200 cash and
a FREE trip as a Vantage
Chat with an Expert
Promo Code: WB50500
Please provide this promotion code to your Vantage call center agent.