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Your Independent Medicare Broker

William Gray

Founder of The Medicare Dude · Licensed Since 1998 · Independent Medicare Broker

FL License #W690237Independent — No Carrier BiasNearly 30 Years Experienceus U.S. Air Force Veteran
Verified Google Review

"Very Knowledgable and personable! William made a seemingly difficult transition easy and seamless. I appreciated his unbiased opinion and personalized what was best for me. He took great care in listening to my concerns. I never felt rushed and felt he took a personal interest in assisting me to make the best choice. Not one of those "Big box" sales as seen on TV. Highly recommend William."

Sharon H

Medicare client

5 ★ · 83 reviews

Google

How to Sign Up for Medicare Part D

Medicare Part D enrollment happens through Medicare.gov. Use the Plan Finder to compare every plan available in your ZIP code based on your specific medications — then enroll directly on the site.

Go to Medicare.gov Plan Finder
5 · 83 Google Reviews
Nearly 30 Years Experience
13 MA Carriers · 8 Supplement Companies

How to Use the Medicare Plan Finder

1

Go to Medicare.gov

Visit medicare.gov and navigate to the Medicare Plan Finder. This is the official CMS tool for comparing all Part D plans available in your area.

2

Enter your ZIP code

Part D plan availability varies by location. Enter your ZIP code to see the plans offered in your area.

3

Enter your prescriptions accurately

Add each medication by name, dosage, and quantity. Accurate drug entry is the most important step — it determines which plans cover your medications and at what cost.

4

Select your preferred pharmacies

Add the pharmacies where you fill your prescriptions. Plan costs can vary significantly depending on whether your pharmacy is in-network or preferred.

5

Compare plans — look beyond the premium

Review total estimated annual drug costs (premium + deductible + copays), not just the monthly premium. A $0-premium plan may cost more overall if your medications are on higher tiers.

6

Enroll through Medicare.gov when ready

Once you've selected a plan, you can enroll directly through Medicare.gov. Have your Medicare number and personal information available.

Ready to compare plans?

Open Medicare.gov Plan Finder

Medicare.gov is the official U.S. government site for Medicare plan comparison and enrollment.

Enrollment Periods & the Late Penalty

Initial Enrollment Period (IEP)

7-month window around your 65th birthday

Starts 3 months before the month you turn 65, includes your birthday month, and ends 3 months after. This is your first opportunity to enroll without a penalty.

Annual Enrollment Period (AEP)

October 15 – December 7 each year

You can switch Part D plans, join a plan for the first time (if you have a qualifying exception), or drop a plan. Changes take effect January 1.

Late Enrollment Penalty

Permanent — added to your premium for life

If you don't enroll in Part D when first eligible and don't have other creditable drug coverage, you'll pay a penalty of 1% of the national base premium for every month you were without coverage. This penalty is permanent.

Have questions about Part D?

William Gray is an independent Medicare broker who can help you understand how Part D works, explain the difference between plan tiers and formularies, and answer questions about your specific medications before you shop on Medicare.gov. His guidance is free and carries no obligation.

Want to understand how Part D coverage works before you shop?

Read the Part D overview
5· 83 Google Reviews

What Clients Say

"I contacted William to assist my wife and I after moving to Florida from another state. He contacted us immediately and scheduled a phone appointment for the following week. We spent about an hour getting to know each other and our needs. He recommended several companies to match our needs and our location here in FL that we would NEVER had figured out on our own. Praise the Lord for Bill and for his help!! I would recommend him to anyone and everyone!!"

Jim M.

Medicare client · Verified Google Review

"Working with William Gray on my Medicare selections was an outstanding experience. Navigating Medicare can feel overwhelming, but William made the entire process simple, clear, and stress-free. He took the time to understand my specific needs, explained every option in a way that was easy to grasp, and offered thoughtful guidance without ever making me feel rushed or pressured."

Julie K.

Medicare client · Verified Google Review

"ABSOLUTELY GOD SENT! I knew nothing about Medicare and close to panicking before speaking with William. Super professional, well informed and kind! Anyone out there approaching 65 years old needs someone like William in their corner; he walked me through each step and all the options best suited my needs!!! All at NO COST because he is paid through the insurance companies."

JKC

Medicare client · Verified Google Review

"Navigating the healthcare system is complex to say the least. This is where The Medicare Dude, William Gray, shined for us on the road to consummating an ideal configuration for our unique and collective situations. William is not just a registered healthcare broker professional, but he is also a wealth of knowledge and sage consult in our best interests. He's always available when questions arise."

TinaKelvin B.

Medicare client · Verified Google Review

"I required an insurance broker with comprehensive knowledge in the field, and William Gray exceeded my expectations. He visited my home and provided a thorough explanation of various Medicare products. As a result, he helped me select the best supplement and achieve a significant reduction of over $150 per month in premiums."

Debra A.

Medicare client · Verified Google Review

"Very Knowledgable and personable! William made a seemingly difficult transition easy and seamless. I appreciated his unbiased opinion and personalized what was best for me. He took great care in listening to my concerns. I never felt rushed and felt he took a personal interest in assisting me to make the best choice. Not one of those "Big box" sales as seen on TV. Highly recommend William."

Sharon H.

Medicare client · Verified Google Review

Showing 6 of 83 verified Google reviews

Questions About Medicare Part D?

William can explain how Part D works and help you understand your options before you shop on Medicare.gov. Free, no obligation.

Licensed in FL, GA, ID, IN, KS, KY, MI, NC, OH, PA, TX, VA · Independent · No cost to you

The Medicare Dude

The Medicare Dude is the marketing brand of The Gray Insurance, an independent Medicare insurance agency helping beneficiaries across Northeast Florida compare Medicare Supplement, Medicare Advantage, and Part D plans from multiple carriers — at no cost.

The Medicare Dude, LLC | The Gray Insurance.

State Licenses

FL License #W690237

FL Agency #L134055

GA #3718523 · ID #1345734

IN #4150677 · KS #1345734

KY #DOI-641736 · MI #1345734

NC #1345734 · OH #1606069

PA #1309973 · TX #3305385 · VA #1467411

Not a government website. The Medicare Dude is not affiliated with, endorsed by, or connected to the Centers for Medicare & Medicaid Services (CMS), the U.S. Department of Health and Human Services, or any federal or state government agency. We do not offer every product available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. We are a licensed, independent insurance broker. We represent multiple insurance carriers and may receive compensation from the carriers whose plans we sell. This does not affect the cost of your plan.

© 2026 The Medicare Dude. All rights reserved.

Agency License: The Gray Insurance · FL Agency License # L134055  ·  Individual State Licenses (William Gray): FL #W690237 · GA #3718523 · ID #1345734 · IN #4150677 · KS #1345734 · KY #DOI-641736 · MI #1345734 · NC #1345734 · OH #1606069 · PA #1309973 · TX #3305385 · VA #1467411