2019 Colorado Academy Cuba Program

Dear Families, Friends, and Travelers – Welcome to the 2019 Colorado Academy Upper School Cuba Program! We have created two webpages dedicated to this once in a lifetime experience so that travelers are as informed as possible throughout the process. This page, the Pre-Enrollment page, is meant to share exciting details, highlights, and pertinent info which participants will want to know before enrolling. Once enrolled, the Post-Enrollment page is intended to prepare travelers for participation on the adventure ahead. Please be sure to review the information thoroughly and get excited for Cuba!
Travel Dates: May 26, 2019 - June 1, 2019
Group Organizer(s):
WTT Contact:
Deadline(s): Interested travelers should enroll by November 9th

Cuba Cultural Journey

A mere 90 miles off the coast of Miami, Cuba was once a popular destination for American tourists until politics, revolution and international intrigue got in the way. Today the island nation is a mirage in the minds of most travelers, a mysterious yet romantic place where cigars, antique cars, baseball and a bearded dictator loom largest. Cuba is place of dichotomies that leave your mind spinning: iconic revolutionaries and disillusioned expatriates, white sand beaches and industrial yards, decaying infrastructure and a highly educated population. The paradox of its proximity and isolation seems only to add to Cuba’s charm.

We are thrilled to offer a program that will see our participants digging deep into the history and modern reality of Cuba. We will meet with local community and government leaders, visit with farmers, hike along mountain trails, dance salsa and much more. Viva Cuba!

Cultural Journeys

Cultural Journeys

Cultural Journeys allow travelers to gain insights into the heritage, history and modern realities of their destination by offering a broad diversity of experience. We rely on the expertise of our local staff to plan itineraries which not only explore the prominent sites but also make time for the lesser-known local gems and are intentional about regular interaction with local people.

Program Highlights

Check out some of the featured experiences of your program!

Have the adventure of a lifetime with your friends

Wander through Habana Viejo, the crumbling and iconic section of this famous city

Visit the cities of Santa Clara, Cienfuegos and Trinidad, a gorgeous beachside town!

Listen to live music on the streets of Havana and engage with local musicians

Meet with renowned local historians to learn about Che Guevara, Fidel Castro and the roots and consequences of the revolution

The Itinerary

We do everything possible to run safe, engaging, and immersive programs for our travelers, but given the unpredictable nature of international travel we must remain flexible in our planning. Changes to a schedule are uncommon but if inclement weather pushes us off course or an unexpected opportunity arises which travelers are excited about, we reserve the right to adjust programming in the best interest of the group. 

DateDay LocationActivity Lodging
May 23SaturdayDenver, CO & Havana, CubaAfter a night time arrival in Havanna we'll head straight to our casas for dinner and a short orientation meeting. Havana Casa Particulares
May 24SundayHavanaThis morning we'll enjoy a tour of Old Havana, focusing specifically on some of the more interesting architecture and public spaces. After lunch we have the unique opportunity of visiting a boxing gym and drumming workshop, both of which cater to teens. Havana Casa Particulares
May 25MondayHavanaAs much as any other country on earth, modern-day Cuba is tightly associated with two personalities: Che & Fidel. How did a medical doctor and avid traveler turn into two of the world's most famous revolutionaries? Today we'll delve into the story of the friendship that changed the history of Cuba forever with visits to the Cuban Revolution Museum, Che Guevara's home, la Plaza de la Revolucion.

In the afternoon we'll visit Fusterlandia, a neighborhood which was claimed by a community of artists and converted into folk art kingdom. We'll also meet with Emprendadores, a local group of young entrepreneurs. Did we mention you'll be rolling through Havana the entire day in classic convertibles?
Havana Casa Particulares
May 26TuesdayHavana & Las TerrazasThis morning we're off on a day trip to Las Terrazas, a UNESCO Biosphere Reserve and secluded eco-village of artists, coffee growers and ecologists about one hour from Havana. We'll visit Hotel Moka, one of first ecological hotels in the world, and check out an old coffee plantation. We'll also do a beautiful hike in the surrounding hillsides which culminates with an relaxing dip in some natural swimming holes. Then we head back to our casa particulares in Havana for the night night. Havana Casa Particulares
May 27WednesdayHavana, Santa Clara & TrinidadAfter breakfast we are off to Santa Clara! On the way you'l check out Finca Vigia, where Hemingway spent much of his time. We'll also visit Muraleando which is an inspirational community arts center. After lunch we arrive at Che Guevera's Mausoleum and the famous, if quirky, train museum. This day will provide the group an opportunity to engage in open debate about Che and his role in Cuban revolution, the circumstances of his death and his legacy throughout wider Latin America.

After our afternoon in Santa Clara we head to the idyllic town of Trinidad, a one of a kind, perfectly preserved Spanish colonial town and UNESCO World Heritage site on the southern coast of the country.
Trinidad Casa Particulares
May 28Thursday Trinidad & CienfuegosWe'll take a walking tour of the city this morning before heading to the Playa Ancon for the afternoon. After sunset we'll enjoy a celebratory dinner before our flight back to the States the following day. Cienfuegos Casa Particulares
May 29FridayCienfuegos, Havana & DenverToday we're up early for breakfast and a departure back to the airport in Havana for our flight home.Your own bed, eventually!


In order to provide a safe and memorable experience, we follow strict guidelines when choosing program accommodations. Walking Tree partners with locally-operated, three-star equivalent hotels and guest houses which are centrally located, clean and safe. 

Below are the accommodations we anticipate using on your trip, subject to availability. 
Casa Particular

Staying in casa particulares is the best and most memorable way to travel through Cuba. One of the few places where free enterprise is allowed to flourish, these homes are managed by Cuban families who also serve as the hosts. Many of the homes are quite impressive!

Safety and Support


I thought all in all it was a great experience and wonderful program!! My daughter speaks about her experience daily. She had a ball!!

Parent of Jaylah, traveler on 2017 Program to Costa Rica

Your Adventure Includes

Program Tuition Excludes: Premiere travel insurance, baggage fees, airline minor fees, passport/visa fees, laundry, souvenirs, and activities not listed on itinerary.

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Resource center

Resource Center

Why should high school students travel abroad? What happens if a participant gets sick? How quickly do we need to enroll? We’re sure you have plenty of questions and we’ve got you covered! Visit our Resource Center to discover the answers to your most pressing questions and contact us anytime with additional questions.

Learn More