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A Community for Creativity, Empowerment, and Imagination

The Island Academy of Hilton Head is a full-time, educationally-innovative K through 12 learning program.


At the Island Academy, students:

  • are known and respected as unique individuals.

  • personalize their education with individualized learning plans.

  • engage in small-group, collaborative learning supported by master teachers.

  • enjoy individualized support and guidance made possible by the 8:1 student-teacher ratio.

  • learn through a rigorous, integrated, project-driven curriculum, designed to support creativity, innovation, mastery, and life-long love of learning.

  • regularly and purposefully explore, interact, and engage with their community and natural world.

Classes meet Monday through Thursday from 8:45 am until 3:30 pm and Friday 8:45am until 1:30pm.


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School Calendar for 2019

We are excited about this extraordinary year so far and to come! Stay updated with events this school year.  If you cannot find for what you are looking, contact us! We love hearing from you. 



Our Team

Our Team

Our Team

Mary Ann Cyr, Head of School

Mary Ann is one of the founders of The Island Academy.  She has her B.A. in Economics and Russian History from the University of Pittsburgh, an M.A. in Education and History from Tufts University, and a C.A.G.S. in Computers in Education from Bridgewater State College.  In addition, she held Principal’s and Superintendent’s licenses from Massachusetts.

Mary Ann has taught at all levels including college, worked as a computer software trainer, and owned a private school for ten years in the Boston area.  

In addition, she authored a monthly column called Women’s Work in the Business Journal of Southeastern Massachusetts, hosted a weekly television program by the same name, invented and developed the board game, olelo, and has served on numerous philanthropic boards. 

She and her husband, Gerry, are parents to three sons, Adam, Nathaniel, and Gabe, and grandparents to Jack and Benjamin. 

Mollie Lynes Kinard, Leader/Middle and Lower School Educator

A native of Hilton Head Island, Mollie holds a B.S. in Anthropology from the College of Charleston, is a certified yoga instructor, and has completed her doula certification through DONA International.  She brings her passion for educating children and a strong belief in experiential learning to all her classes.

Her experience in education began when she moved to North Padre Island, Texas, first as a substitute teacher and then as a paraprofessional in an elementary school inclusion class.  Returning to Hilton Head Island, she worked for a time at Outside Hilton Hear and then found her way back to education at Sea Pines Montessori School. 

Mollie says The Island Academy offers her the ability to share her excitement for teaching with the opportunity to help her students become life-long learners.

She enjoys traveling the world, spending time with her family, and being a perpetual student.


Leonard Ciliento, Leader/Elementary and Middle School Educator

After graduating high school in New Jersey, Lennie moved south to attend the University of South Carolina. While employed as a home remodeler on Hilton Head, he met his future wife Jennifer. Inspired by her educational background, he returned to school to pursue a career in education. Within time, their two sons, Jacob and Ryan, were born.


Marilee Willey, Leader, Educator

As a student athlete, Marilee majored in History and Art History at St. Lawrence University.  Upon graduation she found employment at the Maine Historical Society where she assisted in documenting their broad art collection.  

Drawn to the West Coast, Marilee worked in marketing the scholarly journals Annual Reviews, Inc. followed by a position in the air quality division at the Electric Power Research Institute.  Interested in learning the ins and outs of independent bookstore ownership, Marilee relocated to Colorado to work at the Boulder Bookstore.  A move “back home” to Vermont led to meeting her husband and subsequently raising her three daughters.  

Since moving to Hilton Head in 2008, Marilee has been certified and employed as a massage therapist and certified as a Montessori Teaching Assistant most recently teaching at Sea Pines Montessori Academy.

Marilee finds great happiness and inspiration from life’s never-ending opportunities to broaden our understanding of the world and she is thrilled to experience this joy with the children at Island Academy.


Emma Malinoski, Leader, Educator


Emma moved to Hilton Head Island, SC from Bemus Point, NY in 2015. She has her B.S. in Elementary Education, M.A. in Literacy and a Master Naturalist certification. Emma has always been an avid reader and shares her love of literacy with all ages of students. 

Emma is excited to start her first year at The Island Academy. She hopes to spread the love of reading and writing in creative and innovative ways with her students. 

She enjoys exploring the nature of the Lowcountry and walking her dogs on the beaches of Hilton Head with her wife, Sara.