The Village School of Naples, an independent school serving students in Preschool through 12th grade, announced the appointment of Jeff Cavallo as its Head of Middle School. In this role, he will oversee the school’s sixth through eighth grade division. Cavallo succeeds Andrew Miranti, who was recently named Athletic Director.

Cavallo brings an exceptionally strong and successful career as a leader, teacher, coach and administrator. Most recently, he served as Dean of Students, Boys Varsity Head Basketball Coach, Department Chair, Communications Arts Teacher and Director of Remote Learning for The Benjamin School, a private day school in Palm Beach, Florida.

“Jeff is one of the finest and most well-respected colleagues I have had the pleasure to work with in my career,” said Dennis Chapman, Head of School for The Village School of Naples. “His extensive experience and knowledge will be a valuable asset in leading our Middle School faculty and students and throughout the entire TVS community.”

Cavallo received his Bachelor’s degree from Eastern Connecticut State University and his Master’s degree from St. Thomas University in Miami Gardens, Florida. In 2023, he plans to earn his Doctorate in Leadership and Innovation from St. Thomas University.

Cavallo began his career as a classroom teacher at Bishop Feehan High School (his alma mater) in Attleboro, Massachusetts. After that, he served as Director of Admissions and Head Basketball Coach at Chaminade-Madonna College Preparatory School in Hollywood, Florida. He will be relocating to Naples this summer with his wife, Niki.

Located at 6000 Goodlette-Frank Rd., The Village School of Naples originally began as The Caring Place Preschool in 1985 as an outreach at North Naples United Methodist Church. In 2000, the church relocated to the present campus location and added The Village School, beginning with K-2 and 37 students. In 2006, the school was accredited by the Florida Council of Independent Schools and the Florida Kindergarten Council.

In 2009, parents asked The Village School for a middle school to be added and soon after added the middle school one grade a year to complete the eighth grade. Four years later, the Board of Directors voted to add an upper school with 17 students in the fall of 2017.

In June 2020, The Village School celebrated its first-ever graduating class of seniors with a class of 12 students. The school currently has over 100 upper school students, including 18 in the graduating class of 2022. For information, visit

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