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  • Time to explore the hidden treasures of this island nation
    Two Perfect Weeks in Cuba
    Time to explore the hidden treasures of this island nation
See the dates
  • 15 night cruise
  • Expert lecturers and group leaders
  • Multi - day calls & overnights
  • Visit Finca Vigía, Hemmingway's home
  • 3 UNESCO sites
  • 16 Days
Port charges
  • $499
Cuba fees & charges
  • $126
  • Victory 1
Book by Jan 31, 2018 to get 2 passengers for the price of one! ( based on double occupancy)

Cuba 360° Cruise - Two Perfect Weeks in Cuba

Experience Cuban culture the most authentic way possible – through its people.

On this circumnavigation cruise of Cuba, get acquainted with Cubans in their daily lives, from the beautiful Santiago de Cuba to the colonial architectural haven of Trinidad, to the colorful, cultural city of Havana , and much more. Engage with people directly in discussions about their lives and work, culture and traditions. Meet with Cuban historians, artists, musicians and naturalists and experience this diverse island through their eyes.

Take advantage of our inaugural year savings:

2 for 1 Pricing on the Best Small-Ship Cuba Cruise

37% less than our competitor's best offer

Learn more about this offer.


20 Apr 2018
Miami to Miami
  • Cat E
    $3,999 p/p
    $7,998 before 2-for-1 Promo
  • Cat D
    $4,999 p/p
    $9,998 before 2-for-1 Promo
  • Cat C
    $5,449 p/p
    $10,898 before 2-for-1 Promo
  • Cat B
    $5,749 p/p
    $11,498 before 2-for-1 Promo
  • Cat A
    $5,999 p/p
    $11,998 before 2-for-1 Promo
  • Cat AA
    $6,249 p/p
    $12,498 before 2-for-1 Promo
  • Owner's Suite
    $6,799 p/p
    $13,539 before 2-for-1 Promo
For a full description of the cabins, please see the ship page.


Click on each day to see additional details on the destination and the exciting excursions that are included in your cruise fare.
Day 1
Embarkation Miami, Fl
Cuba Cruise Starting in Miami
Cuba Cruise Starting in Miami

This afternoon guests will embark on the Victory I for an iconic round trip journey from Miami to circumnavigating Cuba, and returning to Miami.  This evening, enjoy a Welcome Reception as well a highly informative talk of the journey that unfolds in front of us.

Day 2 - 3
At Sea
Cuba Cruise - Hotel Ambos Mundos
Cuba Cruise - Hotel Ambos Mundos

While sailing over the Cuba, enjoy relaxing days at sea with engaging, cultural and historical talks with our expert Cuba lecturures. Enjoy the exceptional food and free flowing wine and spririts though out your day. 

Day 4 - 5
Santiago de Cuba
Cuba Cruise - Castillo Santiago
Cuba Cruise - Castillo Santiago

Fidel Castro proudly began the Cuban revolution in Santiago in 1953, and triumphantly announced victory here in 1959. Aside from its revolutionary history, Santiago represented a center of colonial power, boasting an array of important buildings and residents. We’ll visit the Cathedral of Santiago, completed in 1526, and incredibly, destroyed four times by earthquake in 1678, 1766, 1852 and 1932. The Cathedral is located in Cespedez Park, where you’ll find even more well-preserved Colonial architecture. 


We’ll explore the Castillo de San Pedro de la Roca—better known as El Morro—inscribed on the UNESCO World Heritage List as “the most complete, best-preserved example of Spanish-American military architecture.” This multi-level stone fortress built into the rocky promontory of El Morro has guarded the entrance to Santiago de Cuba Bay since 1638. Continuing on, we’ll tour the Cementerio de Santa Ifigenia to observe some of the most beautiful burial crypts in Cuba. We will learn about Jose Marti, a Cuban National Hero whose writing inspired Cuba’s bid for Independence from Spain. He led an invasion force in 1895 and was martyred in battle well before independence was finally won in 1898.


Your People to People experience includes a visit to Casa del Caribe - two former mansions converted into a cultural research institute - to learn about Cuba’s popular Afro-Cuban religion, Santeria. You can meet local practitioners, and even get a divination reading from one of the local espiritistas.  That is, if you are interested in the opinion of the Lucumi deities.


We will continue our discovery of Spanish/Cuban luminaries at the former home of Diego Velazquez, one of the most famous painters of the Spanish Golden Age of the 17th Century. His home, now a museum, is the oldest standing example of colonial architecture in Cuba.  We will enjoy a light lunch at a local Palador (family restaurant), then there will be plenty of free time to explore Old Santiago on your own.


We will continue our People to People tour of Santiago de Cuba by experiencing Afro-Franco-Haitian and Cuban folkloric dance, courtesy of the dance troop, Cutumba. They combine the choreographies of gaga, merengue-haitiano, tumba francesa and rumba to the rhythmic sounds of the island. We will then board a bus tour of Antonio Maceo Revolution Square and Moncada Barracks where, former Cuban President, Fulgencio Batista led a 1952 coup d’etat to begin his reign as dictator until the 1959 revolution, led by Fidel Castro. We will also visit El Cobre Sanctuary where the highly-revered Virgin of Charity (Virgin Mary) statue is housed. It is said that she assists her people and is credited with many miracles. 

Day 6
At Sea
Day 7 - 8
Cuba Cruise - Dancer in Trinidad
Cuba Cruise - Dancer in Trinidad

Our tour of Casilda and the larger Trinidad area begins with a visit to Manaca Iznaga Sugar Cane Plantation where you can try the Guarapo - the sweet juice of the sugar cane. We will continue to a majestic Mirador overlooking of the Valle de los Ingenios. This UNESCO Heritage Site - which is actually a series of three interconnecting valleys consisting of San Luis, Santa Rosa, and Meyer - is home to three sugar mills in-production from the late 18th century until the late 19th century. 


Your People to People tour includes a connection with one of the most artistic families of Trinidad. Ever since the 19th century, when Modesto Santander learned pottery from a Spanish immigrant, the Santander family has been synonymous with the clay pottery of the region. You’ll visit the pottery studio and learn how the family trade has been passed down through generations.


Trinidad is a meticulously well-preserved Spanish colonial city, with rich architecture, cobblestone streets, palaces and plazas. As a result, it is sometimes referred to as the “museum city of Cuba.”  Walk through the town with a representative of the Office of the City Historian, interacting with artisans like Lazaro Niebla, who preserves his heritage through beautiful reverse wood carvings of his elders and ancestors. You’ll also visit the Casa del Crochet, a collaborative project of 35 local women. Next, you can stop in to see Yudit Vidal and her Pincelada Colonial Cuban Art Gallery to browse local artist’s handiwork.


Finally, we’ll survey the Museo Romantico (Romantic Museum), where we are transported back to sugar plantation life.  Housed in one of the former private mansions, you can see a well-preserved example of how 18th Century plantation owners would have lived. 

Day 9 -10
Cienfuegos, Cuba
Cuba Cruise to Cienfuegos
Cuba Cruise to Cienfuegos

Cuba’s Perla del Sur (Pearl of the South) has long seduced travelers from around the island with its elegance, enlightened French spirit and feisty Caribbean panache.  If Cuba has a Paris, this is most definitely it.  Arranged around the country’s most spectacular natural bay, Cienfuegos is a nautical city with an enviable waterside setting. Founded in 1819, it’s one of Cuba’s youngest settlements, but also one of its most architecturally interesting, a factor that earned it a UNESCO World Heritage Site listing in 2005. Geographically, the city is split into two distinct parts: the colonnaded central zone featuring the elegant Paseo del Prado and Parque Martí; and Punta Gorda, a thin knife of land slicing into the bay with a clutch of eclectic early 20th-century palaces, built primarily by Americans under the Batista regime.  


We’ll take in the unique UNEAC (Writers and Artists Union), which features lovely outdoor gardens hosting local music performances. Also on the Jose Marti park, we’ll find the Tomas Terry Theater, built in 1888 by the generous donation of Venezuelan industrialist Tomás Terry, featuring Carrara marble, gold-leaf mosaics, and ceiling frescoes. As part of your People to People tour, you’ll get to meet the Chorus of Cienfuegos, which performs at the theater. Their repertoire includes Renaissance, Baroque, Classical, Romantic and contemporary choral works.


Cienfuegos - Bay of Pigs


A coach will take us to Playa Giron, one of the two landing sites for the 1961 Bay of Pigs invasion - a doomed effort by 1,500 Cuban expatriates to unseat Fidel Castro, shortly after the revolution. Our trip to the local museum will give us the Cuban perspective on the CIA-sponsored invasion.

Day 11
At Sea
Day 12-15
Cuba Cruise - Havana Capitol Building
Cuba Cruise - Havana Capitol Building

Havana is buzzing with an eclectic, sophisticated mix of museums, galleries, music, and dance.  Frequent open-air festivals take full advantage of the island’s sunny Caribbean climate. Our first day in the city, we’ll visit Havana Vieja (Old Havana), a UNESCO World Heritage site, and the charming colonial squares of Plaza San Francisco, Plaza de Armas, Plaza de la Catedral (Cathedral Square) and Plaza de la Revolution (Revolution Square). If you’re interested in the arts, Museo de Bellas Artes (Museum of Fine Arts) will acquaint you with over a century of Cuban fine arts, while our People to People tour will introduce you to what’s happening in today’s Cuban art scene.  We visit projects like Muraleando, a community art project born out of the difficult period of the early 1990’s after the collapse of the Soviet Union and its support for Cuba.  You’ll meet contemporary artists like world-renowned, Kcho, or the unique barbershop/arts center, Arte Corte.


Your People to People experience also connects you with a private dress rehearsal of the unique dance ensemble “Havana Queens” - combining classical ballet, flamenco and modern dance with Rumba and Salsa influences - inviting you to join the unique Caribbean rhythm of the Island. Havana’s rich musical history is best embodied by the Buena Vista Social Club - an actual member’s club which closed in the 1940’s, but the music lives on thanks to sthe band by the same name.  If we’re lucky, we will meet Omara Portuondo, the sole surviving member of the original band.


The second day, we will drive to the outskirts of Havana to visit Finca Vigia, Ernest Hemingway’s home in Cuba. This beautiful property is where the Nobel Prize-winning author lived with his third wife Mary for over 30 years.  See the home in perfect condition with Hemingway’s personal belongings as he left them.  Walk the grounds to see his private writing studio, swimming pool, and beloved fishing boat, Pilar.  The boat is featured in his novel Islands in the Stream. This is also where he wrote several novels such as For Whom the Bell Tolls and The Old Man and the Sea. We’ll even drive to Cojimar, the fishing village where he kept his boat, and which served as the setting for The Old Man and the Sea. 


Use your spare time to catch a ride in Cuba’s most iconic tourist attraction, the 1950’s classic cars.  After the 1959 revolution, Cubans were forbidden to buy foreign vehicles, so the entire country has become a rolling car museum. While ’55 and ’57 Chevy’s dominate the scene, you’ll find well-preserved Buicks, Fords, Oldsmobiles and Plymouths ready to take you back in time. 

Day 16
Miami, Fl
Cuba Cruise - Disembark in Miami
Cuba Cruise - Disembark in Miami

Arrive in Miami. After breakfast on board, disembark for the airport for your flight homeward bound.

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