Chip Gaylor received his B.A. from Asbury University in 1986, his J.D. from the American University Washington College of Law in 1989, and his Master of Laws in Estate Planning (LL.M.) from the University of Miami School of Law in 1990. Chip is a member of the Florida Bar Association and the Sarasota County Bar Association, where he served as President in 2017-2018. He is a member of the Real Property, Probate, and Trust Law Section of both bar associations, and was a Past Chair of the local bar section. Chip is also a member of the Venice Estate Planning Council.

Chip served on the Board of Directors of the Community Foundation of Sarasota County, Inc., and was Board Chair from 1995 to 1997. Currently, Muirhead, Gaylor, Steves & Waskom, P.A. serves as general counsel to the Foundation. He joined the New College Library Association Board in 1998 and was elected President for two terms in 2000. In 2003 Chip was elected to the Board of the New College Foundation, where he chaired the Development Committee. He is an adjunct professor at Manatee Community College.

From 2002 to 2006, Chip served on the Board of SCOPE (Sarasota County Openly Plans for Excellence). In 1999 he was elected to the Board of Directors of the Atlanta-based Southeastern Council of Foundations, and served two years as Board Chair. Additionally, Chip has served on the boards of the Sarasota County Arts Council; the Venice chapter of the American Center Society, the Laurel Civic Association, and the Community AIDS Network.

Chip is a native of Sarasota County and, in his spare time, enjoys traveling, fishing, scuba diving, and tennis. He is a member of the Sarasota Yacht Club, and served on the Board of Directors and Governance Committee.