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 Funeral Home
Naples Funeral Home
Lynette Bailey
April 24, 2025, 11:39 am
Heaven Gained A special Angel on April 14 th 2025 I will forever miss my loving uncle Rick and I have to say he was also a great uncle to two wonderful nieces. He and I had a special bond that will never be broken I loved him so much and I always looked up to him. He was a wonderful man that will be missed by All that knew him but he will never be forgotten .My uncle Rick would do anything and go that extra mile to help anyone in need. He was a very gentle loving ,caring guy .He was always my hero and always will be .I have so many very happy memories of him . Like I can remember when he would come over and mom would say hello Rick and I would come running from the back porch my arms raised Hi and he lit up with a smile . He always had a smile .May he rest in peace until we meet again. We love you and always will
Lynette & Richard Bailey and Family
April 24, 2025, 11:54 am
Heaven Gained A special Angel on April 14 th 2025 | will forever miss my loving uncle Rick and I have to say he was also a great uncle to two wonderful nieces. He and I had a special bond that will never be broken I loved him so much and
I always looked up to him. He was a wonderful man that will be missed by All that knew him but he will never be forgotten .My uncle Rick would do anything and go that extra mile to help anyone in need. He was a very gentle loving ,caring guy
•He was always my hero and always will be .I have ne will never be torgotten.My uncle kick woula do anything and go that extra mile to help anyone in need. He was a very gentle loving ,caring guy
•He was always my hero and always will be .I have so many very happy memories of him. Like I can remember when he would come over and mom would say hello Rick and I would come running from the back porch my arms raised Hi and he lit up with a smile. He always had a smile.May he rest in peace until we meet again. We love you Today , Tomorrow , Always .
Ebbie
April 26, 2025, 4:26 am
Rick was my only brother and I have so many good memories of him
Even tho we lost touch for many years I still loved him dearly. If I had one wish it would be getting back the closeness we once had.
I’m will love and miss you so much.
You left us way too soon, but I know GOD needed you to come home.
Your work here was done. Even tho I don’t know why and I know I never will. Just know I’m sorry and I will always love you. Until we meet again.
RIP little brother.
Linda Parker
May 10, 2025, 11:25 pm
Heaven sure did gain it another wonderful angel he will be very helpful up there in heaven. He was a great guy that I remember and Dorothy and he both were such wonderful caring loving people. We don’t know the reason these things happen but there must be some answers that will find out someday. Hugs and love to you Dorothy and your family I know how sad you are I only hope that you can remember the wonderful life you have and be grateful and know that you too will meet again God bless you till then and God bless your family rest in heaven dear Rick.
Debbie crawford
May 11, 2025, 12:18 am
So sorry for your loss may he watch over you and remember all the good times ♥️♥️♥️♥️
Bobby Floyd
May 16, 2025, 5:29 pm
Rick will always have a very special place in our hearts. We will never forget his infective laughter. We loved him very much.
Debbie Pickering
May 16, 2025, 6:30 pm
Im so sad and sorry about Rick. I feel for all of you. Im Marshall’s moms good friend. I was blessed to know Rick and theventire family. I hurt for you all. God bless you all. Always remember all the good he brought to you all!! ❤️❤️❤️❤️
Diane Baglio
May 16, 2025, 9:55 pm
I’m so sorry for your loss Dorothy . Rick was a great husband, father and friend to all he meet He will be missed by all
Naples Funeral Home
May 17, 2025, 1:59 pm
Rick, we grew up having a lot of good times. We didn’t really drift apart, we just didn’t talk as much as we should have. But you always knew I loved you. Spread your wings with the others who are up there. And keep watching from above. I love you always, Aunt Iona.
Naples Funeral Home
May 17, 2025, 2:14 pm
Even though you weren’t my uncle. I called you uncle Ricky. It was a form of love and respect especially because you meant a lot to me . We’ll miss you dearly and you’ll always be my uncle Ricky, love Sandee