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zAll-Inclusive Cuba Cruise by Small Ship - 14 Day

14 days

Cruise roundtrip Miami aboard the mv Victory I

Our People-to-People Discoveries

+ Experience Cuba’s cultural traditions as we introduce you to artisans, painters, singers and dancers all across the island.
+ Immerse in the alluring Afro-Cuban rhythms of Santiago de Cuba and visit the magnificent 17th-century fortress of San Pedro de la Roca.
+ Spend two days getting to know Trinidad where historic buildings of Neoclassical, Moorish and Spanish Baroque heritage provide context for the city’s vibrant culture.
+ Explore Cienfuegos… Known as the Pearl of the South, this lovely coastal town is distinguished by its unusual ensemble of 20th-century, French-inspired villas.
+ Discover the wealth of Colonial-era architecture in Old Havana as you mingle with city residents along its historic cobblestone streets and stroll through lively town squares graced with handsome Baroque landmarks.
+ Visit Finca Vigia, the handsome home where Ernest Hemingway lived and worked.
+ Discover the diversity of Cuba’s privately-owned paladares and savor wonderful island cuisine on our special shoreside dining experiences.
+ Relaxing days at sea are enhanced with enriching talks with our shipboard experts, well-versed in Cuban history, politics, life and culture.
+ Includes 4 UNESCO World Heritage sites

Click Here to see our 15-day Cuba Cruise >>
Click Here to see our 16-day Cuba Cruise >>

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Welcome to Miami + Board the mv Victory I

You’ll be met at the airport and escorted to the Port of Miami to board our ship. Enjoy a briefing and then dinner as we cruise across the Florida Straits. Meals D


On our way to Cuba

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 over the next 2 weeks will enhance your cruise. Fine dining, our Open Bar and the congenial camaraderie of your fellow travelers enhance your day at sea. Meals B+L+D


Cruising around Cuba

Enjoy another delightful day of cruising as we sail around the eastern tip of the island toward our first 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 Santiago de Cuba

From the unique white dress you’ll see worn by Santeria initiates throughout the city to the region’s distinctive styles of music and dance, Santiago de Cuba has a very strong Afro-Cuban spirit. This morning, you’ll learn more about this unique heritage as we begin two full days of guided sightseeing and people-to-people cultural activities. One highlight of this first day is sure to be the Plaza Delores. Once a bustling marketplace, this pleasant and shady town square is home to popular restaurants and cafes – making it a great place to feel the lively rhythms of the city. As our ship will be docked here overnight, our onboard meals may be enhanced with a specially arranged shoreside dining experience to sample the island’s fine cuisine at a family-owned paladar.  Meals B+L+D


Santiago de Cuba + San Pedro de la Roca

Our second day of sightseeing and people-to-people activities in this vibrant town may include an expertly guided tour of San Pedro de la Roca. Built by the Spanish in the 17th century, this massive stone fortress is spectacularly set on a rocky promontory overlooking Santiago de Cuba Bay. Now recognized as a UNESCO World Heritage Site, it is one of the best examples of Colonial military architecture in the Americas and reflects Italian and Renaissance design principles. Early this evening, we continue our voyage along the southern coast. Meals B+L+D


Along the southern coast

Delight in another day of congenial conversation, fine meals and informative talks with our onboard Cuba experts. Meals B+L+D


Our First Day in Colonial Trinidad

The handsome Colonial-era town of Trinidad is another UNESCO World Heritage Site. The main square is a veritable living museum, surrounded by historic buildings that reflect Neoclassical, Moorish and Spanish Baroque influences. Founded in the 16th century, Trinidad’s many architectural landmarks include the historic Palacio Brunet and the Palacio Cantero, built with wealth from the region’s lucrative sugar trade. With a full day to explore ashore, a great place to begin our guided sightseeing is the Museum of Architecture, where you’ll learn not just about the town’s history but also the background behind its UNESCO designation and ongoing preservation efforts. Our elegant ship will be docked here overnight, giving us another opportunity to dine ashore and experience not just island-cuisine but the city’s vibrant street life.  Meals B+L+D


Another Day in Trinidad

With its picturesque setting against the Escambray Mountains that rise to the north of town, we’ll enjoy a second day of guided exploration in this beguiling city. In addition to its architectural wealth, Trinidad like so many Cuban cities boasts a lively cultural scene, which we’ll experience today with more people-to-people activities. The Ballet Folklórico de Trinidad is just one such group that we might spend time with today. Early this evening, the mv Victory I will set sail again on a westerly course toward Cienfuegos. Meals B+L+D


Ashore in Cienfuegos

Established in 1819 and known as the Pearl of the South, this is one of the island’s newest settlements. It’s also a UNESCO World Heritage Site, recognized for its architectural diversity including a fine Colonial district and a collection of early 20th-century palaces set on a thin slice of land that extends into the picturesque bay. We’ll arrive early this morning and spend the day exploring its architectural landmarks, getting to know its people, and experiencing its rich cultural traditions.  Meals B+L+D


Cruising along the Southern Coast

Enjoy another day of cruising as we chart a westward course. Enriching talks from our experts continue along with the convivial camaraderie of your fellow passengers – all enhanced by wonderful meals, free-flowing wine and our Open Bar.  Meals B+L+D


Day at Sea + Evening Arrival in Havana

Having rounded the western tip of the island, today finds the mv Victory I sailing along the north coast toward Havana. Delight in this day of congenial conversation with your fellow passengers, sit down to a fine lunch with free-flowing wine, take advantage of our ship’s Open Bar, and enjoy presentations from our Cuba experts. Early this evening, you’ll want to be on deck as we sail into Havana Harbor. After dinner, we might have a chance to go ashore and take in a lively jazz performance at one of Havana’s celebrated nightclubs.  Meals B+L+D


A Day + Night in 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 - including colorful old buildings with arcades, balconies and delicate wrought-iron gates. You’ll step off this morning after breakfast for an expertly guided tour designed to showcase these landmarks, recognized by UNESCO as a World Heritage Site.
We’ll be docked here for a second night, so there might well be another opportunity this evening to dine ashore in one of Havana’s fine privately-owned paladares… And possibly experience more of Havana’s famous nightlife!  Meals B+L+D


Life + Culture in the Capital

As the capital of Cuba, Havana offers not only its World Heritage architecture, but also terrific opportunities for more people-to-people engagement. Spending time with city residents from a variety of backgrounds will give you a richer, and more nuanced understanding of Cuba at this important moment in the island’s history. Visiting Hemingway’s hilltop residence where he lived and wrote for nearly 20 years and engaging with local artists would also contribute valuable insights into the city’s cultural legacy.  Late this afternoon, our ship will begin its return voyage to Miami. Enjoy a final gourmet dinner onboard, accompanied by free-flowing wine and our ship’s 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 free homeward flight. Meals B

Our people-to-people Cuba voyages are individually programmed and are in compliance with U.S. Government regulations. 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 itinerary prior to departure will detail each day’s full program.

Cuba MapSearch

Port charges are additional at $499 pp. A Cuban visa and medical insurance are required for $126 pp.