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Around Cuba by Small Ship - 14 Days

14 days

SAVE up to 50% + FREE 1-Category Upgrade

Extended Stays in Port + Deeper Cultural Engagement + More Exploration

+ Begin your immersion in Cuban history even before leaving the USA at the historic San Carlos Institute in Key West; founded by Cuban exiles in 1871, it played an important role in the island’s independence from Spain.
+ Discover the wealth of Colonial-era architecture in Old Havana, Trinidad and Cienfuegos.
+ Visit Finca Vigia where Ernest Hemingway lived and worked for 20 years.
+ Experience Havana nightlife as it was in the 1950’s as we join the living legends of the Buena Vista Social Club for a concert at the historic Capri Hotel.
+ Meet the fishermen of Cojimar, the seaside village that inspired The Old Man and the Sea.
+ Experience Cuba’s cultural traditions as we introduce you to painters, artisans and dancers in their workshops and studios.
+ Savor island cuisine on our special shoreside dining experiences at some of Cuba’s finest privately-owned paladares.
+ Tour Cuba’s oldest surviving mansion and visit the 17th-century stone fortress of San Pedro de la Roca.
+ Relaxing days at sea are enhanced with enriching talks with our shipboard experts, well-versed in Cuban history, politics, life and culture.

Visit 5 UNESCO World Heritage Sites c

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Welcome to Miami + Board the mv Victory II

You’ll be met at the airport and chauffeured by private car to the Port of Miami to board our intimate ship for this exclusive cruise around Cuba. This evening, enjoy a Welcome Reception and Dinner before an informative talk with our shipboard Cuba experts – a great introduction to the journey ahead.  Meals D


A Stop in Key West

The southernmost point in the United States, Key West is beloved by visitors and residents for its vibrant street life. You can also experience colorful chapters of Cuban and American history here. This morning, we’ll explore all of this on a narrated Trolley Tour and a visit to the San Carlos Institute. Founded by Cuban exiles in 1871, and fondly dubbed La Casa Cuba by Jose Marti, the Institute helped to unite the exile community in the fight for Cuba’s independence from Spain.

After lunch the afternoon is free to enjoy as you wish. Duval Street is famous for its bars, cafes and shops. It’s a great place to stroll at your own pace. Hemingway fans may want to stop by Sloppy Joe’s, one of the author’s favorite hangouts. The Ernest Hemingway Home & Museum is another option. It’s located at 907 Whitehead Street in the heart of Old Town Key West. Step back in time and tour the rooms and gardens that witnessed the most prolific 10-year period in his writing career.  Meals B+L+D


Discover Old Havana

Havana was founded in 1519 and within a hundred years it had emerged as one of the Caribbean’s wealthiest ports and an important ship-building center. Although it’s now a vibrant city with more than two million residents, its historical core still retains a wonderful mix of Baroque and Neoclassical architecture. Focusing first on Old Havana c, our guided tour takes us along the city’s cobblestone streets and through its four main town squares – each with its own distinctive charm and fine Colonial-era landmarks. We’ll also drive along the waterfront Malecón, past the University of Havana and through Vedado – an upscale district where classic, mid-century Havana chic has been seemingly frozen in time.

We’ll end our sightseeing at the San Jose Craft Market; it’s one of the best places in the city to shop for Cuban art and handicrafts and offers a chance to engage with local artisans and merchants.

This evening after dinner, we’ll go ashore to experience a bit of Havana nightlife as it was in the 1950’s! The city is rich with music history and no group is more famous than the Buena Vista Social Club. In the atmospheric Salón Rojo at the landmark Capri Hotel, we’ll join the living legends of the Social Club for an unforgettable concert.  Meals B+L+D


Life + Culture in the Capital

After breakfast, we’ll head outside of town to Finca Vigia, the handsome hilltop home where Hemingway wrote two of his most famous works – For Whom the Bell Tolls and The Old Man and the Sea. Peering through its open windows, you’ll see hundreds of the author’s personal belongings almost exactly as he left them when he departed Cuba for the last time in 1960.

Then continue to Cojimar, the picturesque seaside village that inspired The Old Man and the Sea. Spending time with local fishermen is another rewarding cultural encounter. After lunch, we’ll be treated to a private rehearsal with MALPASO - followed by a chance to meet with the talented performers of this independent dance company, founded in 2012 by a trio of renowned Cuban dancers.  Meals B+L+D


A Leisurely Day at Sea

This relaxing day is enriched by talks with our shipboard experts; delving into a wide variety of topics from politics and the arts to the continually evolving relationship between our two nations, our shipboard program will enrich your cruise. Fine dining, our Open Bar and the congenial camaraderie of your fellow travelers enhance this day at sea.  Meals B+L+D


On our way to Cienfuegos

Enjoy another delightful day of cruising as we sail along the island’s southern shores toward our second Cuban port of call. Enriching talks with our shipboard Cuba experts continue along with wonderful meals and our Open Bar.  Meals B+L+D


Ashore in Cienfuegos

This morning, our exploration into the life and traditions of the Cuban people continues at a farmers market. See the variety of local fruits and vegetables for sale and experience an authentic slice of island life. Then we’ll tour Cienfuegos c, recognized by UNESCO for its rich architectural diversity, which we’ll explore first in Punta Gorda. Driving along this thin slice of land that extends into the bay, we’ll discover a fine collection of early 20th-century palaces – many built by wealthy Americans during the Batista regime. Back in the center of town, we’ll enjoy a walking tour through the finely preserved Colonial district.

After lunch onboard, we’ll return ashore for more People-to-People activities: Our first stop is at UNEAC, an organization of Cuban writers and artists. We’ll meet with its director to learn how the center is helping its members to follow their talents and passions. UNEAC Members even include school-age children, and we’ll be treated to a performance by these young musicians. Then we’ll explore the neighborhood, stopping into galleries and studios to engage with the artists.  Meals B+L+D


Valley de los Ingenios + Colonial Trinidad

After breakfast we’ll journey into the Valley de los Ingenios c, a UNESCO World Heritage Site that offers insight into the history of Cuba’s sugar cane industry. At the San Isidro de los Destiladeros Archaeological Site, dating back to the pre-industrial age, we’ll see the original hacienda, a 3-story bell tower and slave quarters. Erected in 1750, the graceful majesty of the 7-story Manaca Iznaga Tower belies its original purpose to observe and control the slaves toiling away in the surrounding sugar cane fields. Today, an ascent to the top reveals the Valley’s pastoral and timeless beauty.

Next we’ll meet with the skilled artisans of the generations-old Santander Family Pottery Studio whose works adorn Trinidad’s historic town square. Over lunch at a local paladar, we’ll have a chance to engage with the owner and staff of this privately owned restaurant. In the afternoon, we’ll enjoy a walking tour through the Colonial heart of Trinidad c. Cited by UNESCO as a World Heritage Site, the town’s historic buildings include the Palacio Brunet and the Palacio Cantero, built with wealth from the region’s lucrative sugar trade.

Our guide will also introduce us to the life and works of Yudit Vidal Faife, a local painter who has exhibited her works throughout Cuba and Europe. We’ll also visit the gallery and workshop of Lazaro Niebla Castro, a wood carver of rare skill, vision and passion.  Meals B+L+D


A Day at Sea

Enjoy another day of cruising as we chart a eastward course along Cuba’s southern coast. Enriching talks from our experts continue along with the convivial camaraderie of your fellow passengers – all enhanced by wonderful meals and our Open Bar.  Meals B+L+D


Santiago de Cuba + San Pedro de la Roca

Fidel Castro launched the Cuban Revolution in Santiago in 1953 and declared victory here six years later. But the town’s importance goes back hundreds of years earlier to its days as a center of Spanish Colonial power. Starting with these earliest days, we’ll tour the 16th-century mansion of Diego Velázquez, the Spanish Conquistador who served as the first Governor of the island. It’s now a fine museum filled with period furnishings.

We’ll have lunch at El Morro, set on a seaside bluff with spectacular views. Nearby is one of Cuba’s most famous UNESCO World Heritage Sites: The Castillo de San Pedro de la Roca c. Built by the Spanish in the 17th century, this massive stone fortress is spectacularly set on a rocky promontory overlooking Santiago de Cuba Bay; it is widely recognized as one of the best examples of Colonial military architecture in the Americas.

Before returning to ship, we’ll spend time at Casa del Caribe, founded 35 years ago to preserve Caribbean culture. Spending time with the Casa’s members offers a chance to learn about their spiritual beliefs and daily life.  Meals B+L+D


History + Culture in Santiago de Cuba

Our first sightseeing stop this morning will be at Santa Ifigenia Cemetery. Home to impressive burial crypts and mausoleums, this is a great place to learn about the historical figures buried here including the Cuban national hero José Martí. Our tour will be timed to coincide with the Changing of the Guard – a moving spectacle of pomp and ceremony!

We’ll also enjoy a performance by Ballet Folklórico Cutumba. Blending African, European, Haitian and Cuban styles, this company has performed around the world. After the performance, we’ll have time to meet with the dancers. In the afternoon, we’ll visit Revolution Square, a park-like plaza dominated by a monumental bronze statue of Lt. General Antonio Maceo astride a rearing stallion. At the Moncada Barracks, we’ll learn about the events that unfolded here on July 26, 1953 when the 26-year-old Fidel Castro set out with 122 followers to attack the military barracks.  Meals B+L+D


A Delightful Day of Cruising

Enjoy this relaxing day at sea and another chance to engage with our shipboard Cuba experts. Today’s talks and discussions will help you to contextualize all that you have learned and experiences thus far.  Meals B+L+D


A Final Day at Sea

Delight in another day of cruising as we continue our homeward journey toward Miami. Enjoy our final shipboard talks, wonderful meals, congenial conversation with fellow passengers and our Open Bar.  Meals B+L+D


Disembark in Miami

After breakfast, you’ll disembark in the Port of Miami. We include your return transfer to Miami Airport for your homeward flight. Meals B

Our people-to-people Cuba voyage is individually programmed and fully compliant with all current U.S. Government regulations for U.S. Citizens traveling to Cuba. Many of the places we visit and the cultural experiences we provide are not in standard touristic venues and are not always available. Thus, your final sightseeing itinerary may vary slightly from what is presented here.


FREE Cabin Upgrade  

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a free 1-category cabin upgrade.
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Prices above reflect 50% discount. Port charges are additional at $499 pp. A Cuban visa and medical insurance are required for $126 pp.

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