A Life-Changing Trip to Cuba


A Life-Changing Trip to Cuba

Where Music Permeates Every Corner

 By NAfME Member Stephen Holley


When asked about my first trip to Havana, Cuba, I’m often at a loss for words. How do I describe a trip which, quite literally, changed not only how I engage my students, but the foundation of how I teach? How do I elevate the conversation past questions of the embargo, the crumbling infrastructure, and la Revolución to help others better understand the Cuban people and their incredibly rich, diverse culture?

Becoming a Student Again

In the fall of 2011, I had the once in a lifetime opportunity to travel to Cuba, with a small group of music educators. The purpose for our trip was to learn more about the Cuban education system and to develop relationships with our Cuban colleagues. The diverse group, a collection of NAfME members spanning both secondary and university educators, first met at the Miami International Airport while awaiting our short flight to Havana. From a professional development standpoint, traveling to Cuba was the beginning of again becoming a student and learning more about clave, the various percussion instruments and rhythms, and the similarities and differences between traditional western music and the music of the Caribbean islands that continues to this day.

If I were to sum up our time in one phrase, it would be life changing.

During our time in Cuba we were able to meet with musicians, teachers, students, recording engineers, policy advisors, teaching college faculty, as well as observe classes at several of Havana’s conservatories. At the conservatories, we were welcomed with open arms, heard several of the students perform, and we even received some conga lessons from the master teachers at Escuela de Roldán! Our evenings were spent eating, dancing, conversing, and listening to as much live music as possible.

Photo courtesy of Stephen Holley


If I were to sum up our time in one phrase, it would be life changing. Truly, I’ve been fortunate enough to travel the world, and the Cuban people were some of the most pleasant, accommodating, and intriguing people I’ve had the pleasure of meeting!

On one night, in particular, two of my colleagues joined me until 3am on the Malecón, the often-photographed seawall that borders the northern edge of Havana, as we took advantage of the cool temperatures, the smell of the ocean, and interesting conversation with a handful of locals who were more than happy to share their experiences with us.

Photo courtesy of Stephen Holley


In the end, my first experience in Cuba was everything I thought it would be and nothing like I anticipated at the same time. It is true, the buildings were crumbling and there were late 1950s American cars everywhere, but what I really took from my time on the island was the kindness of the Cuban people and how music permeates every corner of their society. Even our tour guide knew how to salsa dance and clap clave!

The closest comparison I can make to the city of Havana would the musical city of New Orleans. If you’ve been lucky enough to visit the Crescent City, try to remember how prevalent music is in Jackson Square, around the French Market, at the end of the streetcar line in Carrollton, off Frenchmen Street, and a dozen other hot spots in and around town. Music and New Orleans go hand-in-hand, and the same can be said for music and Cuba. Perhaps this similarity is not a coincidence, as Cuban music had a resounding effect on the music of New Orleans and vice versa, but that is another article entirely!

On our last night in Havana, our group was having one last late night drink at the Hotel Ambos Mundos, where Ernest Hemingway often stayed while in Havana. It couldn’t have been a more perfect ending; as the night wore on and we reminisced on our experiences, a street musician softly sang Chan Chan, a song by Cuban legend Compay Segundo and made famous by the Buena Vista Social Club.


Back to Havana, with Students

Our trip affected me to the extent that when I returned to my school in Denver, I immediately asked my administration how I might be able to travel with my students to experience Cuba as well. As chance would have it, my Upper School division head’s previous school had sent students to Cuba, so I didn’t need to hurdle the “Cuba, are you kidding me?” question!

After quite a bit of discussion, we scheduled our travel over a week in March 2014. Two of my faculty colleagues and I travelled with twenty-five high school musicians, along with our guest artist, jazz saxophonist Javon Jackson, to Havana via Miami. We traveled on a group people-to-people license issued by the US Treasury Department’s Office of Foreign Assets Control. As of September 2017, you are no longer allowed to travel on an individual people-to-people license, but you are still permitted to travel on a group license.

We chose to travel over the week of our spring break, and our group was based in Havana for a full week. During that time, we took salsa dancing lessons, visited four of the music conservatories in Havana, snorkeled in the Bay of Pigs, took a bike tour of Havana, attended a baseball game, and had an awe-inspiring adventure taking in the sights, smells, food, and sounds of Cuba. In the evenings, we sought out live music and, in one rather serendipitous moment, were able to see the Buena Vista Social Club at the Karl Marx Theater!

As educators, we strive for the “aha” moments in rehearsals and on stage. There are too many memories and moments to share in this blog, but . . . One memory that stands out is from our first night in Havana. After dinner in la Habana Vieja that included a live band and dancing, we all spilled out on the streets. There were two street musicians outside, and by the time I exited the restaurant, one of my musicians was playing guitar while all my students, and most of the restaurant patrons, were singing Guantanamera at the top of their lungs!

Another memory was during our time at La ENA, one of the aforementioned high school conservatories. One of my bands played for the Cuban music students, followed by the Cuban students performing for us. My students were eager to practice their Spanish while the Cuban students were eager to practice their English and, before the ENA director or I could say or do anything, the students began to jam on Stevie Wonder’s “Superstition.” Conversations in two languages filled the room with the musicians switching back and forth between the more traditional R&B groove and a songo groove. It was incredible to see our students interacting and enjoying each other’s music.


Photo courtesy of Stephen Holley


In addition to bringing home our memories from the island, my students and I wanted to find a way to give back. With the help of my good friend Susan Sillins at Horns to Havana, and generous donations from several music companies including Jamey Aebersold Jazz, Vandoren, Vic Firth, Alfred Publishing, and Thomastik Infeld, we were able to bring hundreds of pounds of music, strings, teaching resources, reeds, drum sticks, and several woodwind and brass instruments to the students of the Escuela de Manuel Saumell.


study abroad
Photo courtesy of Stephen Holley


I yearn to go back to Cuba! It remains somewhat of a forbidden fruit for U.S. travelers, but it’s absolutely possible to travel there. Havana is a beautiful city, but traveling there is not without its difficulties and varying attitudes. There was quite a bit of gnashing of teeth with the planning and the trip itself, but I would wholeheartedly go through the process again, and again, and again! With the recent landfall of Hurricane Irma, I must admit the island, and my friends there, have been on my mind as of late. I’m thinking it might be time to again make the trek.


I’ll be presenting on our trip to Cuba, my experiences, and my opinion on the differences between the Cuban and American education pedagogies at the Colorado Music Educators Association conference in Colorado Springs in January 2018. I look forward to seeing several of my colleagues there!

If you have any questions about Cuba and how to travel there, legally, with your student group, don’t hesitate to contact me at sholley@kentdenver.org.

About the author:

band director

GRAMMY® nominated music educator and NAfME member Steve Holley serves as the Producer for the Commercial Music Program at the Kent Denver School outside Denver, CO. The R&B, soul, salsa, and jazz bands in the CMP have been recognized by DownBeat Magazine’s Student Music Awards over a dozen times, have performed hundreds of gigs throughout the US, and have performed abroad at the Festival del Tambor, Montreux Jazz, and Porretta Soul Festivals in Cuba, Switzerland, Italy, respectively. In addition, the bands endorse JodyJazz Mouthpieces, D’Addario strings and reeds, Evans drums heads, and ProMark sticks. 

Steve holds a BM in Jazz/Classical performance, a MM in Jazz/Classical performance, and an MM in Musicology from the University of Memphis. In addition to being an educator, arranger, performer, and musical entrepreneur, Steve is a sought-after clinician with performances and master classes given at the Jazz Education Network, Association for Popular Music Education, and several state MEA conferences. Most recently, Steve has written several articles for In Tune Monthly, Teaching Music, and multiple blogs and newsletters for NAfME and JEN.

You can follow the Kent Denver Commercial Music Program on FacebookTwitter, and on Snapchat and Instagram @KentDenverMusic.

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