The Medicare Dude is the marketing brand of The Gray Insurance, an independent Medicare insurance agency helping Medicare beneficiaries in Florida compare Medicare Supplement insurance, Medicare Advantage plans, and Prescription Drug Plans (Part D) from multiple insurance carriers. Our licensed Medicare specialists provide personalized Medicare guidance and enrollment assistance at no cost to you.
Your Independent Medicare Broker
William Gray
Founder of The Medicare Dude · Licensed Since 1998 · Licensed in 12 States
"William was absolutely wonderful very professional. Straightforward gave me a better Medicare policy than I have Had for the last six years… Dropped my policy with a new company same policy same coverage By quite a bit!"
Edna Deri
Medicare client
Medicare Made Simple. Finally.
Compare Medicare Supplement, Medicare Advantage, and Part D plans from multiple carriers — at no cost to you. Licensed since 1998.
No pressure. No obligation. Just honest guidance.
Free · No Obligation · Updated Rates
Find Your Best Medicare Plan
Answer a few quick questions and we'll compare plans available in your area.
Prefer to compare over the phone? Call William at 386-871-3858
Medicare Doesn't Have to Be This Confusing
Most people spend hours trying to figure out Medicare on their own. There's a better way.
The noise you're dealing with:
One independent agent. Every major carrier. Zero pressure.
As an independent broker, I represent multiple insurance companies — not just one. That means I can show you every plan available at your address and help you choose the one that actually fits your life.
Let's Talk MedicareFree consultation — no obligation
Independent · Local · No Cost to You
Why Floridians Trust The Medicare Dude
25+ years of independent Medicare guidance in Florida.
Licensed Since 1998
Over 25 years helping Floridians navigate Medicare with confidence.
Truly Independent
I represent multiple carriers — not just one company. You get unbiased comparisons.
5-Star Rated
Consistently rated 5 stars by clients across Northeast Florida.
Always Accessible
Real answers from a real person. Call, text, or email — I respond promptly.
Have questions about your options? I'm happy to walk you through them.
Talk With William: 386-871-3858Free consultation · No obligation · No cost to you
Simple. Clear. No Pressure.
How It Works
Getting the right Medicare plan is easier than you think.
Schedule a Free Consultation
Call, text, or use the online scheduler. No pressure, no obligation.
We Compare Your Options
I pull plans from every major carrier available in your ZIP code and walk you through the differences.
You Choose With Confidence
You pick the plan that fits your doctors, prescriptions, and budget. I handle the enrollment.
No obligation · No cost · No call centers
Medicare Plans We Help With
From Supplement to Advantage to Part D — we cover it all.
Medicare Supplement (Medigap)
Medicare Advantage (Part C)
Medicare Part D
Ancillary Coverage
Why Work With an Independent Broker?
Not all Medicare agents are the same. Here's what makes the difference.
Multiple Carriers
I'm appointed with every major carrier in Florida — Aetna, Humana, UnitedHealthcare, Cigna, Mutual of Omaha, and more.
No Conflict of Interest
I'm paid the same commission regardless of which plan you choose. My only goal is finding the right fit for you.
Annual Reviews
Plans change every year. I proactively review your coverage each fall to make sure you're still in the best plan.
Local Knowledge
I know the Florida Medicare market — which plans have the best networks, which carriers have the best service records.
Medigap Plans
Medicare Supplement Plans
The most flexible Medicare coverage available — accepted by any doctor nationwide who takes Medicare.
Why Medicare Supplement Is So Popular in Florida
Florida has one of the highest concentrations of Medicare beneficiaries in the country. Medicare Supplement plans are popular here because they provide nationwide coverage with no network restrictions — important for snowbirds and frequent travelers.
The Most Popular Supplement Plans
Plan G — Most Popular
Covers everything Medicare Supplement covers except the Part B deductible. The most comprehensive plan available to new Medicare enrollees.
Plan N — Best Value
Lower premiums than Plan G with small copays at doctor visits. A strong choice for healthy beneficiaries who want to save on monthly costs.
High-Deductible Plan G
The lowest premiums of any Supplement plan. You pay a deductible before coverage kicks in — ideal for those who rarely use healthcare.
Who Should Compare Medicare Supplement Plans?
Medicare Supplement plans are a strong fit for beneficiaries who want predictable costs, the freedom to see any Medicare-accepting doctor without referrals, and comprehensive protection against large medical bills. They're especially popular with:
Or call 386-871-3858 to compare quotes over the phone
Part C
Medicare Advantage Plans
All-in-one coverage that often includes benefits Original Medicare doesn't cover.
How Medicare Advantage Works
Medicare Advantage (Part C) plans are offered by private insurance companies approved by Medicare. They cover everything Original Medicare covers, often with additional benefits like dental, vision, hearing, and fitness programs.
Who Benefits Most
Medicare Advantage can be a strong choice for beneficiaries who want extra benefits, prefer a structured plan with an out-of-pocket maximum, and are comfortable using a provider network.
Provider Networks
Most Advantage plans use HMO or PPO networks. We verify that your current doctors and preferred hospitals are in-network before recommending any plan.
Prescription Drug Coverage
Most Medicare Advantage plans include Part D drug coverage. We compare formularies to make sure your medications are covered at the lowest possible tier.
Not sure if Advantage or Supplement is right for you? Call 386-871-3858 — William will walk you through both options.
Not sure which Medicare plan is right for you?
William Gray has helped thousands of Floridians make this exact decision. Call for a free, no-pressure conversation.
Initial Enrollment
Turning 65? Here's What You Need to Know
Your Initial Enrollment Period is a 7-month window. Missing it can cost you.
Your Enrollment Timeline
Your Initial Enrollment Period begins 3 months before your 65th birthday month and ends 3 months after — a 7-month window. Enrolling late can result in permanent premium penalties for Part B and Part D.
Common Mistakes to Avoid
The most common mistake is assuming Medicare is automatic. Part B requires active enrollment. Another common error is assuming employer coverage qualifies as creditable coverage — it depends on the employer size.
Planning Ahead
We recommend starting the Medicare planning conversation 3–6 months before your 65th birthday. This gives us time to compare all available plans and ensure a smooth enrollment.
Special Enrollment Period
Moving to Florida?
Relocating to Florida can trigger a Special Enrollment Period — and a chance to get better coverage.
Florida-Specific Carriers
Florida has a competitive Medicare market with carriers and plans not available in other states. Moving here is an opportunity to compare options you've never had access to before.
Your Special Enrollment Period
Moving to a new service area typically triggers a Special Enrollment Period that allows you to change your Medicare Advantage or Part D plan outside of the Annual Enrollment Period.
Supplement Considerations
If you're moving from a state with guaranteed-issue Supplement protections, you may have a limited window to enroll in a Supplement plan without medical underwriting. Timing matters.
Our Service Areas
We serve Medicare beneficiaries throughout Florida, with deep expertise in Northeast Florida — Duval, St. Johns, Flagler, Volusia, Putnam, Clay, Brevard, and Hillsborough counties.
What Our Clients Say
5-star rated by Medicare beneficiaries across Northeast Florida.
"William was absolutely wonderful very professional. Straightforward gave me a better Medicare policy than I have Had for the last six years… Dropped my policy with a new company same policy same coverage By quite a bit!"
Edna Deri
July 2026
"The most knowledgeable person that I spoke with . Plus was clear and delivered great service Highly recommended ."
C
June 2026
"William listened to my needs and answered my questions thoroughly. I felt comfortable with the plan I chose based on his explanations and Pro's and Con's of certain choices."
Mary Scott
June 2026
"William Gray was a huge help with navigating the "World of Medicare". My husband and I were new to the entire process and had a ton of questions. William broke everything down into understandable terms and walked us through the ENTIRE process! He is always available when we have questions and we had A LOT. William helped us select the plans that would work the best for my husband and his healthcare needs."
Michelle Cooper
June 2026
"I recently moved here from Idaho and William made the transition very easy. He is very pleasant, knowledgeable and honest. I highly recommend him for all your Medicare needs."
Becky Bailey
June 2026
"William, aka “The Medicare Dude,” is fantastic at what he does! He is very honest, presents all the options and makes sure that you understand, which is very important when dealing with insurances. If you or someone you are helping needs help navigate the Medicare process, call William, he is the best at what he does!"
Kit Marshall
June 2026
"We were so impressed with Mr Grays knowledge and the help he gave us on Medicare plans . Very honest and would definitely recommend him to friends and family newly navigating Medicare"
kimberly lingaitis
June 2026
"William Gray is outstanding! He is thorough, patient, highly professional, honest and explains everything so you truly understand. You receive personalized service which is so rare. He's your guy for everything Medicare!!"
sharon priore
June 2026
"The Medicare Dude explained everything on point about Medicare. He returned my calls or messages very promptly. I would definitely recommend him so you don't have to go through the headaches of trying to figure this system out."
Paul Fiore
June 2026
"Very helpful !!!!! Appreciate!!!!"
Susan Stovall
May 2026
Your Medicare Broker
Meet William Gray — The Medicare Dude
Independent Medicare broker. Licensed since 1998. Serving Florida.
I started The Medicare Dude because I saw too many people getting steered into the wrong plans by agents who only represented one company. As an independent broker, I represent every major carrier in Florida — which means my only loyalty is to you.
Over the past 25+ years, I've helped thousands of Floridians navigate Medicare enrollment, annual plan reviews, and coverage changes. I've seen what happens when people choose the wrong plan — and I've made it my mission to make sure that doesn't happen to my clients.
I serve Medicare beneficiaries throughout Northeast Florida — including Jacksonville, Orange Park, St. Augustine, Ponte Vedra, Daytona Beach, Ormond Beach, Palm Coast, Flagler Beach, and communities across Duval, St. Johns, Flagler, Volusia, Clay, and Putnam counties. Two offices. One broker. Always me on the phone.
Whether you're turning 65, losing employer coverage, or just wondering if you're in the right plan, I'm here to help. No pressure. No obligation. Just honest answers.
My Philosophy
The right Medicare plan is the one that fits your doctors, your prescriptions, and your budget — not the one that pays the highest commission. I'll always tell you the truth, even if it means recommending a plan that costs me less.
Free Resources
Medicare Learning Center
Free guides, FAQs, and resources to help you understand Medicare.
Have a question not covered here? Call William at 386-871-3858 — he'll answer it personally.
Medicare Premium Surcharges
IRMAA: The Medicare Surcharge Most Retirees Don't See Coming
If your income exceeds certain thresholds, Medicare charges higher premiums — sometimes hundreds of dollars more per month. Our free IRMAA guides help you understand the rules, plan ahead, and know your options.
Have IRMAA questions specific to your situation? Call William at 386-871-3858 — he'll walk you through it at no charge.
Frequently Asked Questions
Quick answers to the questions we hear most often.
Still have questions? I'm happy to answer them personally.
Ask William Directly: 386-871-3858Two Offices Serving Northeast Florida
Visit us in Daytona Beach or Palm Coast — or we'll come to you. All consultations are free with no obligation.
Ready to Find Your Best Medicare Plan?
Free consultation. No pressure. No obligation. Just honest guidance from an independent broker who's been doing this since 1998.