Karen Mary Maestrales's Obituary
Karen Mary Maestrales, age 68, of Boca Raton, Florida, passed away peacefully at home with her children at her side on June 14, 2026. A beloved Waldorf teacher and visionary award-winning artist, she leaves behind a world made infinitely kinder and more colorful by her presence.
Born on April 6th, 1958 to James Anthony Cholke and his beautiful wife Rita (Prkut) in Chicago, Illinois, she was the oldest of four children and is survived by her three loving siblings Kimberly (Thomas) Styx, James (Shellie) Cholke and Frances (Stephen) Day. She is also survived by her three beloved children, Peter (Francesca), Sophia and Zaqueri (Jennifer) Wilson, and her two grandchildren, Rosalina and Gus, who will forever cherish their memories of “Grammie”. Also left to miss her are a loving extended family, a lifelong circle of devoted friends, and a wide community of students and colleagues who will deeply miss her radiant spirit.
Above all her earthly passions, Karen was a mother and Grandmother whose heart belonged entirely to her family. She was deeply and fiercely devoted to her three children, raising them with the same boundless love, warmth, and spiritual grace that she shared with the world. They were her greatest joy and her proudest legacy.
Deeply devoted to the spiritual philosophy of Rudolf Steiner, Karen spent her life nurturing the minds, hearts, and souls of young children. As a Waldorf educator, she did not just teach; she created a sanctuary of warmth, imagination, and reverence for the natural world.
She generously shared this gift with her community as co-founder of Imagine That - Fine Arts Academy of Boca Raton, Inc. in 1990. Imagine That included early childhood Waldorf Education as well as Drawing, Painting, Sculpting and Mixed Media for young children through teens. Karen taught countless individuals of all ages how to communicate with art and bring the unseen world to life on paper. Her artistic spirit was a true reflection of her inner light.
Beyond the classroom and the canvas, Karen found peace in the earth. She was an avid gardener who spoke the language of flowers and found deep spiritual renewal in the rhythm of the seasons. Her gentle spirit extended to all living things, including her beloved dogs Rocky, Chios and Lola that she shared her life with and dearly loved over the years. Her legacy lives on in the beautiful plants she tended to in her garden, the vibrant paintings she created, and the generations of children she guided with unconditional love.
In 2008 Karen changed gears and co-founded Airstream Jets, a business aviation brokerage and jet card provider with her son, Peter. She dedicated a decade of her life to the company and was integral in creating what has become a highly successful organization renowned in the aviation industry for its customer service and business integrity.
Karen faced profound health challenges in her final years. She met those challenges with grace, resilience, and deep spiritual strength. She continued to share love and light with those around her, and her positivity and courage in the face of incredible difficulty and deteriorating health should be an inspiration to us all, and a reminder that every day we have with one another is truly a gift from God.
To send flowers or plant a memorial tree in memory, please visit our flower store.
In lieu of Flowers Please Consider Donating in Honor of Karen
Karen was a talented painter, an award-winning artist, and a deeply creative human being whose life was devoted to bringing beauty, imagination, and kindness into the world. She had a profound passion for teaching and nurturing young people and spent much of her life studying childhood development and sharing the principles of Waldorf-Steiner education. As a co-founder of Imagine That – Fine Arts Academy of Boca Raton, Karen helped countless children and teens discover their own creativity through drawing, painting, sculpture, mixed media, and a deep reverence for the natural world. In lieu of flowers, we invite those who wish to honor Karen to make a donation in her memory. Contributions will be directed to an organization that reflects the causes closest to her heart—art, childhood development, and Waldorf education—so that her lifelong work of nurturing young minds and encouraging creativity may continue in her name.