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Bailey Group In fact, it can be the opposite. At The Bailey Group, you'll work with a local insurance advisor to find just the right insurance coverage for your specific needs & budget. Our goal is to make getting covered simple, with no added costs or fees. Choosing health insurance is a process I normally dread but Scott's follow up and the ease of getting all paperwork done makes choosing a health plan easy and more affordable than doing it myself.

Andrew was extremely helpful and pleasantly professional. He had a sincere desire to help me with my very complex problem.
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We employ some of the best and brightest talent in the business, dedicated to helping you solve your most complex business and individual challenges. We're driven to find the right answer for you. Whatever your challenge, we can approach it with a fresh perspective and apply our deep knowledge, creative thinking and industry experience to deliver a tailored solution.
Our journey to become one of the largest insurance and benefits firms in the State of Florida began over 60 years ago. The firm of Thompson Bailey Baker, established 75 years ago, was founded by John Thompson and Harold Ryman in St. Augustine, Florida. In 1954, John Bailey becomes a partner in the business.
As with most other things in life, the key to achieving your long-term financial objectives is planning. The best time to review your current life insurance situation is directly before or after a major life event.
At The Bailey Group, you'll work one-on-one with a dedicated agent to find the right Florida Blue plan based on how you actually use your health insurance. We'll run through a number of different factors that come into play to help narrow down the best options for you and your family. Enrolling in a plan on your own can be daunting.
Reviews (12)
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Russ Anderson
Jun 24, 2022
We moved from Arizona to St Augustine three years ago. Arriving in Florida we had no contacts to meet our many of our needs, for example medical insurance. I called several organizations discovered using a Google search and got only one response. Andrew Carle of the Bailey Group. He was responsive, walking me through the initial application process. On the policy anniversary he follows up for renewal. Good organization, excellent service in a challenging business.
Al Schmidt
Mar 07, 2022
I am so thankful for having contacted the Bailey Health Group! Tammy Morabito has been awesome! She helped me to get my Medicare supplement in place at the final hour. She is amazing! She was patient and very informative with the plan I selected. She did all the research on my doctors and medications, it was great! I would defiantly recommend this group and ESPECIALLY Tammy Morabito! Thank you Tammy!
Patti Miller
Dec 06, 2021
I have been with the Bailey Group, specifically Tammy Evans, for 2 years now. She is an expert in her business, she knows Medicare inside and out and is very good at sharing what she knows as well as offering the features/benefits of different Insurance Programs that she feels will fit the needs of each client. Getting to know the client is her first step.

She is very friendly and professional at all times. Answering questions and offering suggestions helps the client decide which Programs will be best. I appreciate her knowledge and professionalism so much that I have referred 3 different friends to her and they too are very satisfied. Selecting an Insurance Product can be overwhelming, Tammy Evans helps simplify it all. She and the Bailey Group are a home-run! Patti Miller
Steg Thompson
Nov 30, 2021
Just moved to Florida. Contacted Tammy. She quickly sent several options for me. We waited to see how my California Insurace would run. At end of October, needed to switch before month end. Was done in an hour, and all set up now. Will contact in a year for help when I turn 65. :
Mimi Cooke
Nov 28, 2021
Having been a Certified Employee Benefit Specialist in my past dealing with the selection of plans for my company, I was amazed that I truly struggled with selecting an appropriate Medicare supplement plan for my husband and me. Tammy Evans has taken the anxiety out of the enrollment period. Thank you Tammy!
Annie K.
Nov 26, 2021
In looking for support in acquiring Medicare insurance for the first time, I found Tammy Evans, of the Bailey Group, to be extremely helpful, patient with all my questions, and very friendly as well as professional. Tammy came highly recommended by some folks I know, and I can see why. It has been, overall, a very positive experience. Thank you, Tammy!
Kc Frierson
Nov 25, 2021
So thankful for The Bailey Group and Tammy Evans in particular. She navigated through the complicated waters of the Health Insurance Marketplace for us and found and secured a health insurance plan to meet our family's unique needs. If you are self employed and need help finding health insurance that is affordable and don't want the hassle and headache of dealing with healthcare.gov yourself, give the friendly folks at The Bailey Group a call and ask for Tammy Evans.
Melissa Clements
Nov 01, 2021
I have put off getting health insurance for many years simply because it is so confusing! Scott McIntosh was professional, courteous, and knowledgeable! It was so easy! I made a call to him and he did the rest! Thank you so much!
Lisa Sanzone
Oct 14, 2021
I have been working on securing health insurance for my husband and I as we were coming off Cobra and wanted to share this. Scott McIntosh has been extremely helpful and has a wealth of information to share with you! Scott responded to me almost immediately and has been thorough and available throughout the entire process. I had done my homework but Scott educated me about the in's and out's and we are so thankful to have him on our side!
Ken Leach
Apr 24, 2021
My wife, Amy, and I have had excellent service provided by Scott McIntosh at the Bailey Group. We both just turned 65 and are new to Medicare. There was a vast amount of information to read and important decisions to be made. Some options were confusing and others vague, but whenever we asked Scott for help, he responded almost immediately, and if he didn't have the appropriate answer then, he would research the question and within a day, he would respond with an easy-to-understand answer. Scott has always been exceptionally professional in his communication and provided us with above and beyond the call of duty information. We can tell that he truly enjoys helping people. Thank you, Scott, for making our transition to Medicare Advantage plan relatively easy and efficient.
Juan Claros
Jan 17, 2021
Scott McIntosh at The Bailey Group has been my Advisor for our health insurance needs for the past years. It has been a fantastic experience. His support and guidance makes me understand our options and make informed decisions. His knowledge and kindness provides accurate and timely information while giving us a peace of mind through the entire process. He is great and I highly recommend him.
Joyce B.
Jun 29, 2020
I have worked with Tommy Delaney for several years now and he is consistently wonderful! He is knowledgeable, dependable, easy to reach, and always kind! He was recommended to me by the school system when I retired and has more than met my expectations. I highly recommend him to anyone needing help and guidance with their health insurance.