Cindy Bailey Holmes

Cindy Bailey Holmes passed away peacefully, surrounded by her loving family, on June 2, 2026.

Born on September 20, 1958, in Myrtle Beach, South Carolina, Cindy was the beloved daughter of the late Max and Margaret Hinson. As the child of an Air Force family, Cindy spent her early years moving from place to place, experiencing different communities and adventures along the way. When she was in elementary school, her family settled in Fort Walton Beach, Florida—a place that would forever hold her heart and become the home she cherished for the rest of her life.

Even at a young age, it was clear that Cindy was bright, beautiful, and exceptionally smart. She possessed a natural gift for understanding people and an intuition that seemed beyond her years. Family and friends often marveled at her ability to read a situation, offer thoughtful advice, and make others feel truly seen and understood. Cindy also loved music and had a beautiful singing voice. It was often said that Cindy was the harmony to her friend Jennifer’s melody, a reflection of the special friendship they shared throughout the years.

Cindy graduated from Choctawhatchee High School and went on to build a beautiful life in Fort Walton Beach. It was there that she raised her family, formed lifelong friendships, and created countless memories that would bring her joy throughout her life.

On October 11, 1985, Cindy married the love of her life, Greg Holmes. Though they were often described as an “unlikely match,” their endless love stood the test of time. Together they built a life rooted in devotion, laughter, resilience, and unwavering commitment to one another. Through every season of life, their love remained constant and served as an example to all who knew them.

In 1987, Cindy opened the doors of her home and began what would become one of her life’s greatest callings—caring for children through her in-home daycare. For nearly two decades, until 2004, “Ms. Cindy” welcomed children into a place filled with love, laughter, learning, and security. Her daycare was much more than a business; it was a second home for countless children and families. Cindy nurtured each child with patience and affection while teaching them valuable life skills, confidence, kindness, and independence. She created an environment where children felt safe, encouraged, and deeply loved. Whether she was planning educational activities, reading stories, or taking the children on exciting field trips to the zoo and other local attractions, Cindy made every day an adventure. Years later, many of the children she cared for still lovingly refer to her as “Ms. Cindy” and remember the lasting impact she had on their lives.

After closing her daycare, Cindy found another meaningful way to serve others when she joined Shelter House as the volunteer coordinator and then United Way as Executive Director of Development. In this role, she was able to give back to the community she loved so dearly. Cindy had a gift for bringing people together, building relationships, and inspiring others to support causes that strengthened the lives of local families. Her work reflected her generous spirit and her lifelong commitment to helping others.

The beach was Cindy’s happy place. She loved the sugar-white sands and emerald waters of the Gulf Coast and never missed an opportunity to share them with the people she loved. It was not uncommon for her to load up a car with grandchildren, family members, or friends and head off for a day by the water. She could spend hours talking about marine life, tides, shells, and the unique beauty of the coast she called home. Her enthusiasm was contagious, and every beach trip became a lesson, an adventure, and a treasured memory.

Some of Cindy’s favorite moments were spent on the boat with her family, especially her grandchildren. She delighted in sharing traditions and creating special memories. One of her favorite rituals was encouraging everyone aboard to throw their hands in the air and let out a joyful scream whenever the boat passed beneath a bridge—a simple tradition that never failed to bring laughter and excitement to every outing.

Cindy was larger than life and possessed a personality that could light up any room. She was often the leader of the pack, the one making plans, organizing gatherings, and ensuring everyone knew exactly where they needed to be and when. She was famous for her back porch parties, where every detail reflected her creativity and enthusiasm. Whether celebrating a holiday, a birthday, or simply being together, Cindy transformed ordinary gatherings into unforgettable events with thoughtful decorations and an atmosphere full of warmth and fun. Her laughter was unmistakable—joyful, contagious, and impossible to ignore. It carried across a room and had a way of drawing people in, making them laugh along with her and feel instantly welcomed.

Above all else, Cindy’s greatest love was her family. She was incredibly proud of her son, Bryan, and the coaching career he built. She cherished her trips to Georgia, where she could watch from the stands as he mentored, encouraged, and inspired young athletes on the field. Cindy also loved Bryan’s sense of humor and never missed an opportunity to laugh at one of his jokes. His quick wit and ability to make others smile brought her endless joy, and she often said he was one of the funniest people she knew.

Cindy also shared a special bond with her daughter, Scarlett, whom she deeply admired. She frequently spoke about Scarlett’s compassionate heart, gentle spirit, and unwavering kindness. Cindy found immense comfort and joy in their relationship and treasured every moment they spent together.

Nothing, however, brought Cindy more happiness than her grandchildren. Her five beautiful granddaughters were the light of her life and the source of endless pride and joy. Whether she was attending their activities, taking them on adventures, spoiling them with love, or simply spending time together, Cindy treasured every moment. They kept her busy, filled her days with laughter, and made her heart fuller than she ever thought possible. She loved each of them fiercely and took great joy in watching them grow into remarkable young women.

Cindy leaves behind a legacy of love, generosity, laughter, and unwavering devotion to family and community. Though she will be deeply missed, Cindy’s spirit will continue to be felt in every beach sunset, every family gathering, every joyful laugh, and every adventure shared with loved ones.

In addition to her parents, Cindy was preceded in death by her brother, Michael Hinson.

Her memory will forever be treasured by her beloved husband, Greg Holmes; children, Bryan Bailey (Heather) and Scarlett Soska; grandchildren, MacKenzie Middleton, Lilly Soska, Aurora Soska, Ava Bailey and Brooklyn Bailey; sister, Pam Barrios (Gary); nieces, Jordan Suhre and Stephanie Durbin; and a host of cherished friends whose love and companionship made them family in every sense of the word.

A Celebration of Life will be held to honor Cindy’s life at a later date.