Upper School Trip

Key Details

  • Approximate Trip dates: March 14 (late evening departure)-28, 2017
  • Group size: 12 students
  • Estimated Cost: $2700–$2900 (Note: cost does not include recommended vaccines and medications.  Please see the CDC website for health recommendations and check with your doctor and insurance carrier about costs.)
  • Trip leaders: Aline Garcia-Rubio, Chris Mateer, Zulema Young-Toledo (student leader)

Student Information Sessions in Library 4: lunch, September 21, and co-cu, September 22

Evening Information Session: 6:30pm, September 28, 2016, Vollum 2

Trip application

Financial assistance request form 

Olive Bridge Endowed Fund for Global Education form

Program Overview

What do you imagine when we speak of Cuba?

“Nestled like a jewel among the glittering waters of the Caribbean, it has been home to mobsters and poets, artists and revolutionaries (Ché Guevara, Fidel Castro and Jose Marti, amongst others).

Cuba is a fixture in the American imagination, a place of legend and mystery, of crushing poverty and unfettered spirit. Its troubled and codependent relationship with the United States has made it eternally relevant, and now, as America prepares to relax its embargo, Cuba, once more, is calling.” (from CUBA, Castro, Revolution and the End of the Embargo. Lightning Guides, 2015)

We will use the lens of the arts –-painting, film production, photography, music, poetry, printmaking and narrative to witness, explore and experience this socialist country and its evolution.

We will share, interact and engage with artists on Cuban soil. Our group will bring together our creativity and artistic talents to understand Cuba and its people. We will explore Cuban’s point of view on the relationships between the United States and their nation. We will use art as a mechanism for normalizing relationships with the people of the island.

Spanish fluency and artistic talent are not prerequisites for students on this journey. Flexibility, curiosity, collaboration and creativity are.


More Information:

Some have described Cuba as “a prince in a poor man’s coat: behind the sometimes shabby facades, hold dust lingers.” Traveling in Cuba is exciting and especially so during this transition time (after more than half a century of embargo and tense relationships with the United States, things are quickly changing). In Cuba, time has moved at a different pace and Western ideas cannot be taken for granted. The architecture of its colonial cities is delightfully preserved so that walking in Havana brings back a different era. There is a slice of Spanish baroque, some French classicism, some art deco and a bit of European Art Noveau. While the people of Cuba have been dealt a difficult life, they are joyous and proud; they are outstanding musicians of son, salsa, rumba and trova who mix African drums and the Spanish guitar. Cubans live in an intricate culture of color and story-telling, poetry, dance and a rainbow of people who have created visual arts that cannot be found elsewhere. We will seek to understand the people, history, strife and pride of Cuba through their art and through our own creative endeavors alone and with others during our time on the island.

During our time in Cuba, we will focus mainly on Havana: Habana Vieja, Centro Habana, Vedado, Marianao and Jaimanitas. While taking in the history and daily life of people in the capital city, we will place an artistic lens on our daily explorations, interactions and creativity. In an effort to see more of Cuban life, we will visit a nearby beach, to experience Cuban life in that setting; we will travel to el Valle de Viñales, a rural valley that offers flat topped hills, with green tobacco fields and various viewpoints that show the beauty of that rural island. We will also stop at Las Terrazas, an ecovillage established during the 60’s when Cubans concerned about deforestation and sustainability built an ecologically minded town and populated it with artists, musicians and coffee growers. Cuba is riddled with more than 20,000 caves; cave exploration is available at all levels; we will leave the difficult treks to speleologists but will visit La Gran Caverna de Santo Tomas, near Viñales.



San Cristobal de la Habana was founded in 1514, in the south coast of Cuba by Spanish conquistador Narvaez. The city was moved twice due to mosquito infestations in the first five years and wasn’t permanently established until 1519. Havana was the most westerly and isolated of Diego de Velazquez’ original villas and life was hard at that time and in the following era, with French pirate invasions and local slaves razing the city.

Once Mexico and Peru were conquered the pendulum swung in Havana’s favor. The location of the island in the entrance to the Gulf of Mexico offered a strategic location for treasure fleets and the regrouping of colonizers. In 1607, Havana replaced Santiago as the capital of Cuba. 

The city continued to be sacked by French pirates and the Spanish built forts to reinforce a protective ring. In the late 1600s and early 1700s, a strong wall around the city was added. These defenses kept pirates at bay but did not defend against the British, who got embattled with the Spanish in the Seven Year’s War.

In June of 1762, the Brits attacked Havana from an unexpected angle and took the city but taking hold of La Chorrera and El Morro. The British held Havana for 11 months. The Spanish negotiated Florida in exchange for Havana in 1763 and created a program to upgrade the city’s defenses eventually making the city the most fortified urban center in the New World.

The British occupation resulted in Spain opening Havana to freer trade and by 1818, the number of trading cities had expanded allowing Cubans to ship sugar, rum, tobacco and coffee to any part of the world. The XIX century brought steady progress: railway, public lighting, the telegraph, urban transport systems, telephones and electricity.

By 1902 the city had a quarter million inhabitants and had expanded west along the Malecon, into the wooded glades of Vedado (vetoed). A large influx of Americans arrived during the start of the Prohibition era and many “good times” rolled with abandon. Havana was a decadent gambling city with all night parties of American mobsters. 

For Fidel Castro, this was an aberration. He took power in 1959 and the revolutionary government promptly closed down all casinos, sending back to Miami many mobsters, gamblers and “investors”. With the arrival of the new political system, the glittering hotels were turned into homes for the rural poor and the decline of the rich era of Havana began.

But, how did that come about? What is the story of the revolution from Batista to Raúl Castro? This, and so much else, we will study together (through art, mostly) in our preparation and during our time in Cuba. 


(this is a rough and, at the moment, flexible itinerary)


Habana Vieja y Centro Habana

An architectural jewel from every era. It holds one of the finest collections of urban edifices in the Americas from intricate Baroque to glitzy art deco. We will surely see the Plaza de la Catedral (a museum to the Baroque, including the city’s beguiling asymmetrical Cathedral from the 1700’s. We will stop by the Taller Experimental de Grafica, Havana’s most cutting edge art workshop, where we might take a class in engraving.

We will wander through Calle Obispo, soaking in the culture, old and new and perhaps shopping for musical instruments at the Longina Musica. Then Calle Mercaderes, with the old shops and eclectic art ending in Plaza Vieja where we might sit down to write, draw or otherwise document what we have witnessed up to that point. During our walk we will consider stopping at the Casona Centro de Arte for some contemporary visual arts or at the Centro Cultural Pablo de La Torriente Brau, where expositions poetry readings and acoustic music are hosted alongside the groundbreaking center for digital arts.

In Habana Centro, the Museo Nacional de Bellas Artes will allow us to look at some of the greatest Cuban artists (Guillermo Collazo, Rafael Blanco, Raul Martinez and Wilfredo Lam).

Other points of interest for us:


We will travel to Vedado and walk the more modern streets to the Fábrica de Arte Cubano, Habana—The brainchild of Afro-Cuban fusion musician X-Alfonso, this is one of Havana’s finest new art projects. An intellectual nexus for live music, art, expos, fashion shows and invigorating debate. In Vedado; we will mingle with artists and mainly Cuban clientele in the evening after 8 pm.

Fusterlandia- Jaimanitas

West from Central Havana, Cuban artista Jose Fuster has turned his home neighborhood into a masterpiece of tiles, turrets and extraordinary Barcelona-like beauty.

The result is what is unofficially known as Fusterlandia, on ongoing Project first hatched 20 years ago that has covered several suburban blocks with whimsical but highly stylized public art. The centerpiece is Fuster’s own studio, a sizeable residence decorated from roof to foundations by art, sculpture and, above all, mosaic tiles of every color and descriptions. The work mixes homages to Picasso and Gaudi with snippets of Gaugin and Wilfredo Lam, elements of magic realism, strong maritime influences, a cap doffed to Santeria, the curves of modernism and a dose of Fuster’s Cuban-ness. We will wander the streets and get inspired by Fuster’s work directly at his Taller-Estudio. We’ll be working on establishing a connection to visit him.

Of note in Havana:

Marianao: Escuela Nacional de Bellas Artes “San Alejandro”

This is the oldest and most prestigious fine arts school in Cuba. Founded in 1818 at the Convent of San Alejandro by the French painterJean Baptiste Vermay, who was its first director. Located in a monumental building from the 1940s, it was established by the Royal Patriotic Society and the Royal Consulate of Havana, as the Free School of Drawing and Painting; these days it offers Painting, Printmaking, Sculpture, and Graphics and Digital Art. The Academy treasures a rich history in its classrooms and the best Cuban artists of all time were formed there. Some of them were directors of this prestigious institution, which today continues to offer teaching Cuban artists.

We are working in with artists affiliated with the school (Rafael Villares, Adriana Arronte y Reynier Leyva) with the goal of working on artistic collaborations with current students. We will spend 3-4 days engaged in this collaboration while students stay with local families.

Other sites and activities that the group will consider visiting in Havana (we will decide this democratically!):

Casas de la Trova – Cuba’s old fashioned music houses that keep the essence of traditional Cuban music alive.

Museo de la Revolucion – Cuba’s comprehensive museum – a one stop immersion in all things revolutionary (?)

La Roca Fort (sketching, photography and writing)—200-year-old fortress (?)

Street Rumba

Casa de la música Centro Habana –One of Cuba’s best and most popular nightclubs and live-music venues. All the big names play here. Big salsa bands with Little space.

Posible playas del Este (Day trip.)

Havana’s very own Riviera, Playas del Este, begins about 11 miles East of the capital at Bacuranao, before continuing to Tarara, El Megano, Santa Maria del Mara and Boca Ciega to the town of Guanabo. The beautiful aquamarine waters draw folks from Havana throughout the year. We will spend a day walking around, writing and perhaps shooting film and photos for a digital production. 

Callejon de Hamel Afro Cuban Rumba

Las Terrazas

On our way to Viñales, we will stop at Las Terrazas, where a vibrant art community with open studios, woodwork and pottery workshops are nestled in an idyllic eco village. Back in 1968, the forward thinking Cubans implemented a plan, taking a 50 square km tract of degraded land around the remains of some of the old French cafetales (coffee farms). They reforested in erosion resistant slopes. The workers of the Project then created a reservoir ad non its shores constructed a village for the people in the region. This is now a thriving community of self-supporting, sustainable settlement.

We will spend the day combining some short (2-5 mile) hikes with local art learning and our own creations. 


From Las Terrazas, we will head to Viñales, one of Cuba’s most magnificent natural settings, wedged into the Sierra de los Organos is a valley steeped-sided by limestone outcrops and peppered with the vernacular architecture of its traditional farms and villages. The impressive geological erosion which shaped the region 100 million years ago left the vast valley and the great cave it contains. Guajiros, the farmers who tended the crops since the late 1700’s run the region, which is still harvests tobacco and maintains its authentic rural life. We will spend three days (two travel days and one on site) exploring the following:

La Gran Caverna de Santo Tomas

Tobbaco plantation

Hiking and horseback riding

Roast Pork with guajiros

Casa de la Cultura and art gallery



Traveling to Cuba is not meant to be a vacation. We are seeking students committed to preparing for the trip as much as those who will juice every minute spent on the island. We need enthusiasts of the arts as much as we need those who love the social sciences and want to explore the creative forces that portray history as well as their own creativity.

Speaking Spanish is not required though it is desirable. A good attitude and your commitment are essential for the trip. Traveling with an open mind, being flexible and expecting surprises, confusion and astonishment are absolute requisites for the trip.

In preparation for our journey, we will meet roughly 3 times a month throughout the school year, beginning in October; most of these meetings might happen during our cocurricular period. 90% attendance to meetings are a requirement for the trip. If you commit to go, you commit to prepare for being there. During these gatherings, we will watch Che: The Argentine (a film), and perhaps other films such as Fresa y Chocolate and Before Night Falls. We (you, mostly) will plan the specifics of our journey and prepare what we each want to explore while in Cuba, as well as the technical and logistical aspects of our artistic work while away. All participants will read a history packet before our departure in addition to a single book of their choice from the following list **:

One Man in Havana by Graham Greene

Cuba and the Night by Pico Iyer

Che Guevara, A Revolutionary Life by Jon Lee Anderson

A History of the Cuban Revolution: Aviva Chomsky

Listen, Yankee!: Why Cuba Matters by Tom Hayden

Waiting for Fidel by Christopher Hunt

Art Cuba: The New Generation by Holly Block

Cuba: A History in Art by Garry Libby

Cuban Revelations: Behind the Scenes in Havana by Marc Frank

**If you want to read a different book, pleas speak with Chris and Aline about it; we will likely accommodate any of your choices.



We will present the trip to the entire Upper School on September 21st. This will be followed by an information session for students on September 21 (cocurricular) and again on September 28 (lunch). Parents must attend the information session on the evening of September 28.

Applications are due on October 3rd. Financial aid is available and requires a separate application.

*Apply here:

We will announce trip participants around October 14 and will need families’ financial commitment confirmed by signing the financial commitment letter by the 21st. The first installment of payment will be billed on December first. There will be a mandatory trip information and safety evening for parents and trip participants later in December.

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