A mere 90 miles from Miami, Cuba was once a popular destination for American tourists until politics, revolution and international intrigue got in the way. Today the island is a mirage in the minds of most travelers, a mysterious yet romantic place where cigars, antique cars, baseball and bearded guerrilla fighters loom largest. Cuba is place of dichotomies: decaying cities occupied by a highly educated population, socialist fervor overlaid with a fascination of America. Cuba's charm is undeniable and we are thrilled to offer a program that pushes participants to dig into history and confront the truths and exaggerations of the island's reputation.

We recognize the extraordinary role that meaningful international travel can play in shaping the lives of young people, and strive to create itineraries which push travelers to see themselves and the places they visit in a new and exciting light.

Walking Tree organizes programs for teachers and their students.
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Sample Itinerary

Walking Tree Travel specializes in customized group travel. The itinerary below is from a recent program and is provided here as an example of just one of many experiences that are possible in this destination.

After a night time arrival in Havana we'll head straight to our casas particulares for dinner and a short orientation meeting.


This morning we'll enjoy a walking 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.


As 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?


This 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.


After 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.


We'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.


Today we're up early for breakfast and a departure back to the airport in Havana for our flight home.


Teacher Spotlight

Spanish Teacher, Colorado

"I just saw some of our students from the Cuba trip and they were raving about it! Thanks again for all of your efforts in making this a great trip- I can confidently say it was the best trip with students I’ve been on."

All-Inclusive Program Tuition

$2,990 + Plane and world iconInternational Flight

Program Types in this Destination

Service AdventuresConservation ExpeditionsCultural Journeys

Don’t see your area of interest highlighted in the itinerary above?
Plan your own customized trip today!

Program Tuition Includes

All accommodations

Three meals per day

Ground transportation

Drinking water

Full time leadership team

Group activity and entry fees

Taxes and tips

Estimated airfare*

Not included: Baggage fees, Airline minor fees, Passport/visa fees, Laundry, Souvenirs, Activities not listed on the itinerary.

*Estimated airfare: In order to give our travelers the best possible price, we break out airfare from the Program Tuition. We will still handle all booking and ticketing via our flight partner who has access to special fares not available to the general public. Families will be invoiced for the flight once we are able to secure the best airfare for the group.

Global Leadership Activities

Walking Tree Travel has developed tools that will help our travelers mature as global leaders before, during, and after their travel program. These simple, engaging activities are meant to spark discussion, frame the group’s experience, and prepare participants to travel ethically and effectively on our programs now and on their own into the future. Our activities also encourage students to take initiative as leaders in their local communities to make a difference at an immediate level, helping them to understand the impact they can have when they combine cultural understanding with personal and social responsibility.

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