In Loving Memory Of
Richard C.A. Bailey
August 2, 1960 -
April 14, 2025
In the care of
Naples Funeral Home & Cremation Services
Richard “Rick” Bailey
Naples, FL
08/02/1960 – 04/14/2025
Richard “Rick” Bailey, 64, of Naples, passed away suddenly on April 14, 2025, following a tragic coach bus accident in which he was the driver. His loss was unexpected and has left a profound void in the lives of all who knew and loved him.
Rick was born on August 2, 1960, in Toledo, Ohio, and had called Naples home since 1968. For many years, he worked as a chauffeur for Naples Transportation and Tours, a role he embraced with pride and heart. Rick was known not just for his driving, but for making passengers feel welcome and at ease—often sharing stories and local history to turn a simple ride into a memorable experience.
Outside of work, Rick was a man of many skills and passions. He loved fishing with his family and treasured time spent on the water. He was also a talented handyman, always willing to lend a hand or fix what was broken—often before anyone even asked. In addition, Rick served as a rifle instructor, teaching others how to handle firearms safely and responsibly—something he took great pride in doing with care and patience.
He also had a passion for cooking and especially enjoyed preparing meals for family gatherings and celebrations. Whether behind the wheel, on the water, in the kitchen, or with a tool in hand, Rick poured warmth and dedication into everything he did. His easy going nature, sharp sense of humor, and generous spirit made him a constant source of comfort and strength to those around him.
Rick is survived by his loving wife of 43 years, Dorothy Bailey; his daughter, Dorothy, Son-in-law Marshall, and his cherished grandchildren, Elizabeth and Alexander Levin. He is also fondly remembered by extended family, friends, and coworkers whose lives he touched over the years.
A celebration of Rick’s life will be held on May 17th, 2025 with services from 2:00–4:00 p.m. and 6:00–8:00 p.m at Naples Funeral Home
The family has entrusted care and services to Naples Funeral Home located at 3107 Davis Blvd, Naples, FL 34104.
-His Daughter Dorothy, is asking for memories of Rick from those who knew him.
Please write a note with your name, how you knew him, and how Richard impacted your life. Dorothy wants to share these with her children. Elizabeth and Alexander only knew him as Pop–Pop and she wants them to know about other aspects of his life. There will be a box for Messages at the service please feel free to share multiple memories if you can. You can also bring a printed note/letter if you prefer, instead of writing it at the service. Thank you so much for being a part of Rick's life.
ZOOM INFORMATION:
https://us02web.zoom.us/j/82650364830?pwd=48w5UASlFD5pXLNKabgNI831i5a1wT.1
Meeting ID: 826 5036 4830
Passcode: 1234
Naples, FL
08/02/1960 – 04/14/2025
Richard “Rick” Bailey, 64, of Naples, passed away suddenly on April 14, 2025, following a tragic coach bus accident in which he was the driver. His loss was unexpected and has left a profound void in the lives of all who knew and loved him.
Rick was born on August 2, 1960, in Toledo, Ohio, and had called Naples home since 1968. For many years, he worked as a chauffeur for Naples Transportation and Tours, a role he embraced with pride and heart. Rick was known not just for his driving, but for making passengers feel welcome and at ease—often sharing stories and local history to turn a simple ride into a memorable experience.
Outside of work, Rick was a man of many skills and passions. He loved fishing with his family and treasured time spent on the water. He was also a talented handyman, always willing to lend a hand or fix what was broken—often before anyone even asked. In addition, Rick served as a rifle instructor, teaching others how to handle firearms safely and responsibly—something he took great pride in doing with care and patience.
He also had a passion for cooking and especially enjoyed preparing meals for family gatherings and celebrations. Whether behind the wheel, on the water, in the kitchen, or with a tool in hand, Rick poured warmth and dedication into everything he did. His easy going nature, sharp sense of humor, and generous spirit made him a constant source of comfort and strength to those around him.
Rick is survived by his loving wife of 43 years, Dorothy Bailey; his daughter, Dorothy, Son-in-law Marshall, and his cherished grandchildren, Elizabeth and Alexander Levin. He is also fondly remembered by extended family, friends, and coworkers whose lives he touched over the years.
A celebration of Rick’s life will be held on May 17th, 2025 with services from 2:00–4:00 p.m. and 6:00–8:00 p.m at Naples Funeral Home
The family has entrusted care and services to Naples Funeral Home located at 3107 Davis Blvd, Naples, FL 34104.
-His Daughter Dorothy, is asking for memories of Rick from those who knew him.
Please write a note with your name, how you knew him, and how Richard impacted your life. Dorothy wants to share these with her children. Elizabeth and Alexander only knew him as Pop–Pop and she wants them to know about other aspects of his life. There will be a box for Messages at the service please feel free to share multiple memories if you can. You can also bring a printed note/letter if you prefer, instead of writing it at the service. Thank you so much for being a part of Rick's life.
ZOOM INFORMATION:
https://us02web.zoom.us/j/82650364830?pwd=48w5UASlFD5pXLNKabgNI831i5a1wT.1
Meeting ID: 826 5036 4830
Passcode: 1234