Roy Boles

Roy Boles, a man who embraced the sea, adventure, and the "Jimmy Buffett lifestyle," passed away on September 11, 2024, at the age of 79. Born on August 19, 1945, in Mobile, Alabama, Roy carried the warmth of the coast with him wherever he went. 

After settling in Lake City, Florida, Roy met and married Judy Edwards. Together, they raised two children and built a home in Gainesville, FL, where they became an integral part of the community. His passion for life, his community and the ocean shaped who he was, and he left an unforgettable mark on those fortunate enough to know him.

A dedicated Gator, Roy planned numerous trips to Florida Gator football games, organizing travel by bus and plane to ensure that The Gator Nation always showed up in full force. His enthusiasm and leadership as President of the Fightin’ Gator Touchdown Club were legendary, inspiring others with his commitment. Roy was also a founding member of the Gainesville Sports Organizing Committee (GSOC), which brought various sporting events to Gainesville, enhancing the city’s athletic culture. He was a man who knew how to get things done, always rallying his community to share in the excitement for the causes he cared about. 

Roy was a proud member of the B.P.O.E. #990 for over 50 years, where he held various roles, including being part of the Friday Night dinner crew. He took great pride in being part of such a wonderful organization and valued the camaraderie and sense of community it brought him. 

Roy’s adventures were not limited to land. A lifelong dream of his was to build a houseboat from scratch, and he made it happen in classic Roy fashion. While sitting at a bar, he sketched out plans for the boat on a cocktail napkin. By chance, he met someone who had two newly built pontoons to spare, and from that moment, the "Royhamas" was born. Roy took great pride in the houseboat and made the daring crossing from Florida to Green Turtle Cay, Abaco, Bahamas—a place that became his home away from home. He adored the Abaco Islands, its people, and its natural beauty, sharing that love with everyone he could. He was affectionately known as “Captain Roy” or “Royhamas”, and whenever “Royhamas was in the house”, a good time was guaranteed. 

In addition to his community involvement, Roy ran a successful roofing company, Boles Roofing, in Gainesville until his retirement in 2006. Roy was also proud to serve in the US Army National Guard, where he was a member of the Pistol Team and won various accolades as a sharpshooter. His service to his country was a source of great pride. 

Yet, Roy’s greatest joy was found in his grandchildren. He delighted in sharing his love for the sea, travel, and adventure with each of them, creating memories they will treasure forever. Whether it was sailing the seas, exploring new places, or simply enjoying time together, Roy left a legacy of love and adventure that his grandchildren will carry in their hearts. 

As Jimmy Buffett once said, "If there's a heaven for me, I'm sure it has a beach attached." Roy is undoubtedly sailing along those shores now, where the sun is always shining, and the music of a well-lived life echoes in the wind.

He will be remembered as a man who lived life to its fullest and for his larger than life personality. 

Roy was preceded in death by his parents, Leroy and Willie Kate Boles and brother, Ronnie Boles. 

Roy leaves behind his two daughters: Chris Hagin and Kim Humphries (Mark); mother of his children: Judy Boles; brother Curtis Boles; sisters Brenda Evans (Fred) and Linda Kent; four grandchildren: Tyler Hagin (Rachel), Justin Hagin, Heston Humphries (Isabella), McKenna Humphries and countless friends that are like family. 

A heartfelt thank you to the staff of Ayers Health and Rehabilitation in Trenton, FL and Haven Hospice for their love, care and support for Roy and his entire family. 

Roy’s life will be celebrated on Sunday, September 22, 2024 at 2pm at 5701 Venue (also known as the Senior Recreational Center) at 5701 NW 34th Blvd, Gainesville, FL. Since Royhamas was more than just a name—it was a way of life—we invite you to wear your favorite Caribbean-style apparel or a Royhamas t-shirt in his honor. No one loved a good party more than Roy, and we hope you’ll join us in celebrating a life well lived. 

If you wish to make a donation in Roy’s honor, the family has requested donations be made to The Green Turtle Cay Foundation (greenturtlecayfoundation.org) or Haven Hospice (beyourhaven.org/donate)