Cuba 9 Night Enhanced Voyage

February 1, 2019 - February 11, 2019

Join the Theodore Roosevelt Medora Foundation on an exciting 9-night Cuba Cruise! Cruise around the island nation of Cuba, stopping at key ports to sample Cuban culture, cuisine, and have people-to-people experiences unavailable anywhere else! Visit the colonial gem of Santiago, where Joe Wiegand will discuss Theodore Roosevelt’s Roughriders, the charge up San Juan Hill, and Spanish-American War, and more!



Contact us or give us
a call 1-800-833-8787
Meet your tour guides
Joe Wiegand

Joe Wiegand entertains audiences nationwide with his portrayal of President Theodore Roosevelt. He has performed for audiences in all 50 states- including a performance at the White House! Since 2012, he has portrayed TR in Medora, ND for the Theodore Roosevelt Medora Foundation. Joe's Theodore Roosevelt shares stories full of adventure, laughter, and inspiration!

  • Local English-speaking guides for shore excursions
  • Presentations by host Joe Wiegand, Theodore Roosevelt reprisor
  • Hosted Cocktail Party

Day 1: Miami, FL

Feb. 1, 2019

Fly from your hometown to Miami, Florida
Overnight in Miami.

Day 2: Embark on the Azamara Journey

Feb. 2, 2019

Enjoy a leisurely morning at the hotel with a noon departure to the pier to board the beautiful Azamara Journey.
TRMF Welcome Social Hour

Day 3: Havana, Cuba

Feb. 3, 2019

Havana is a study in contrasts. A stroll down the Prado through the historic neighborhood of Old Havana, provides a glimpse into the city’s 16th-century heritage.

Day 4: Havana, Cuba

Feb. 4, 2019

Wander along Havana’s beloved oceanside boulevard, the Malecón; enjoy an authentic Cuban lunch at a local paladar, and browse or shop at the Almacenes San José Artisans’ Market.

Day 5: Havana, Cuba

Feb. 5, 2019

Enjoy one more day amongst Havana's architecture and culture.

Day 6: At Sea

Feb. 5, 2019

Enjoy an enhanced educational session onboard with Joe Wiegand, Theodore Roosevelt portrayer. Spend the day sailing in style aboard your boutique hotel at sea.
In the evening, savor excellent cuisine and enjoy shows at the Cabaret Lounge or Living Room.

Day 7: Cienfuegos, Cuba

Feb. 7, 2019

French charm and stunning architecture meet fiery Caribbean spirit on the palm-lined streets and sandy shores of Cienfuegos. At the same time lively and laid-back, warm Caribbean breezes swirl around neoclassical, art nouveau and art deco buildings, and sweeping botanical gardens are bursting with tropical beauty.

Day 8: At Sea

Feb. 8, 2019

Relish a restful day at sea and enjoy an educational session with Joe Wiegand, who will speak about the Rough Riders who were officially known as the 1st United States Volunteer Cavalry Regiment. They had been raised for the conflict in Cuba which would become known as the Spanish – American war. This was a relatively short campaign which ended with a United States victory over Spanish forces, the signing of the Treaty of Paris in December 1898, and the direct United States control of Cuba for several years.

Day 9: Santiago de Cuba, Cuba

Feb. 9, 2019

The 26th President of the United States, Theodore Roosevelt (Joe Weigand) will join us on a private excursion to San Juan Hill. Interpretation provided of the history, battle and ride up San Juan Hill!

Day 10: At Sea

Feb. 10, 2019

Relax on our final full day at sea. Indulge in a treatment at Sanctum Spa, stay ship shape with a class at the fitness center, or lounge by the pool.
TRMF Farewell Social Hour

Day 11: Arrive in Miami and disembark

Feb. 11, 2019

Pricing and Information


Pricing is per person, based on double occupancy


Club Oceanview Stateroom Club Verandah Stateroom
$3,849.00 $4,249.00



Included in your Cuba Cruise Package:

  • 9-night cruise aboard the Azamara Journey
  • Pre-night hotel stay in Miami
  • Transfers between the airport, hotel, and cruise ship
  • All cruise port taxes
  • Gratuities onboard the ship
  • Beverage package
  • Presentations onboard by host Joe Wiegand, Theodore Roosevelt portrayer
  • Private excursion to San Juan Hill in Santiago


Not Included in your Cuba Cruise Package:

  • Cuba tax of $75/person must be paid directly by travelers at embarkation.


Deposit of $400/person due to secure your stateroom.

Second Payment of $600/person due July 31, 2018.

Final payment due September 26, 2018. 

Cancellation Charges Without Traveler’s Protection Plan (TPP):

91 days or more prior to departure: Deposit Amount
90 days to day of departure: 100% of the total tour