About
Diego Retana is a NYC-based guitarist, multi-instrumentalist, bandleader, and studio musician whose work spans jazz, rock, pop, blues, musical theater, and Celtic traditions. With over two decades of musical experience and more than 15 years as a professional performer, Diego has built a versatile career performing, recording, and collaborating across a wide range of musical settings, from intimate acoustic performances to major concert halls and festival stages.
Born in Costa Rica, Diego emigrated to the United States with his family at the age of three and grew up just outside Washington, DC in Maryland. His musical journey began early through singing and the saxophone, before discovering the guitar at age thirteen. Largely self-taught in his formative years, Diego developed his musicianship through deep listening, transcription, and extended daily practice, drawing heavily from recorded music and early online instructional resources. This ear-driven approach continues to shape both his playing and musical philosophy.
During high school, Diego committed fully to music, studying theory, piano, and guitar while also student-conducting his school’s string orchestra. Outside of school, he immersed himself in the instrument, often practicing six to eight hours a day. He later pursued formal training at Frederick Community College before transferring to Towson University, where he earned a Bachelor of Music with a focus on jazz and commercial performance. While his academic studies refined his technical and harmonic command, Diego’s playing remains grounded in feel, adaptability, and musical communication.
As a performer, Diego has appeared at venues ranging from local churches and music festivals to renowned NYC clubs such as The Iridium and Birdland, as well as major cultural institutions including the Kennedy Center and Carnegie Hall. His performance credits include theatrical productions, concert presentations, and original works across genres, reflecting his ability to move fluidly between contemporary, traditional, and theatrical musical worlds.
Diego is an active recording musician and studio collaborator. He appears on Sam & Company, a genre-spanning musical theater album by Sam Nasar, released in 2025, performing both acoustic and electric guitar. Additional recording credits include releases with Mixed State, The Pilgrims of Deep Run, and a range of independent artists and ensembles. His recorded work reflects the same versatility and musical sensitivity that define his live performances.
In addition to his freelance work, Diego maintains several long-standing projects. He performs with Mixed State, a New York City–based jazz-fusion group, and serves as Music Director for The Pilgrims of Deep Run, a Baltimore-based Celtic folk ensemble. Through these groups, he balances improvisation-driven contemporary music with deeply rooted traditional styles.
Alongside performance and recording, Diego is a dedicated music educator. His teaching philosophy mirrors the way he learned himself: emphasizing listening, repertoire, and practical musicianship over rigid methodology. He has taught at the Bel Air School of Music, multiple Music & Arts locations in Maryland, and The Bullis School in Potomac, MD. He currently teaches private lessons and coaches a middle school rock band at The Dwight School.
In 2024, Diego received the Distinguished Artist Award from Frederick Community College, and in 2025 returned as a featured performer for a concert honoring the award, presenting performances with Mixed State followed by The Pilgrims of Deep Run. Today, he continues to perform throughout New York City and beyond, bringing professionalism, adaptability, and a collaborative spirit to every musical setting.
Selected Credits:
Recordings
Sam & Company – Sam Nasar (2025) — Acoustic & Electric Guitar
A Head Full of Fears Has No Space for Dreams – timesink (2025)
The Faller – Sam Nasar (2025)
Espresso Depresspo – Mixed State (2025)
Live at The Music Space – The Pilgrims of Deep Run (2023)
(Be)Loved: The Live EP – PRIYA (2025)
Selected Performances
Miss You Like Hell – Baltimore Center Stage (2019)
Show Way – The Kennedy Center (2022)
FCC Welcomes Guitarist Diego Retana – Concert honoring Distinguished Artist Award (2025)
A Pitch From Satchel Paige – Carnegie Hall (2026)
Awards
Distinguished Artist Award – Frederick Community College (2024)
Videos
Lessons
In addition to his work at The Dwight School, Diego offers private music lessons both in person and virtually. He teaches electric and acoustic guitar, bass, ukulele, mandolin, and Irish/tenor banjo, working with students across a broad range of experience levels, with a particular focus on supporting intermediate and advanced players seeking to deepen their musicianship.
Diego teaches students from approximately age eight through adulthood and believes that musical growth is possible at any stage of life. His lessons are designed for students who want to develop strong technical foundations while also gaining fluency in harmony, rhythm, and style through real repertoire and hands-on application.
Lessons emphasize musical understanding, creativity, and personal expression. While Diego provides structure and direction, instruction is tailored to each student’s goals, whether that means improving improvisation, expanding stylistic vocabulary, preparing for performances or auditions, or becoming a more confident ensemble player. Music is approached as a collaborative art form rather than a competition, with progress always balanced by enjoyment and curiosity.
Private lessons are offered in monthly packages with a consistent, recurring weekly time. Students interested in studying with Diego are encouraged to reach out to inquire about availability and rates and to schedule a complimentary introductory meeting.
Diego.E.Retana (at) gmail.com
Testimonials
“Both my daughter and I wanted to learn how to play the guitar, and Diego was always patient and kind, finding the best learning methods for each of us. Although I eventually stopped lessons due to time constraints, my daughter continued until Diego changed locations. He was always the most polite and professional instructor we worked with. He was so wonderful that I even asked him to play at my wedding. I highly recommend Diego Retana to anyone seeking quality and integrity in the music industry.”
— Leanne M.
“Diego made the class very engaging and encouraging, and he tailored the lessons specifically to my goals.”
— Dan N.
“Diego is a natural teacher with a God-given talent. My daughter has only been taking guitar lessons for four and a half months, but her progress has been incredible. She learns something new each week and leaves every lesson with a big smile. Diego is kind, encouraging, and extremely knowledgeable, with a fun and diverse repertoire. I highly recommend him.”
— Alida W.
“Diego is a wonderful guitar teacher for our daughter. He has fostered a genuine love of music in her. She looks forward to her weekly lessons, and we never have to ask her to practice—she is always excited to continue what she started during the lesson.”
— Ellen O.
“Terrific guitar teacher. I was a beginner, but I’m confident Diego could help students at any level.”
— Jamie P.