Medicare Enrollment Checklist 2026

Medicare Enrollment
Checklist for 2026

Every task you need to complete — in order — to enroll in Medicare correctly and avoid costly lifetime penalties.

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Work through each phase in order. If you have questions at any step, call William — he walks Florida seniors through this process every day at no charge.

3–6 Months Before You Turn 65

Confirm your Social Security enrollment status

If you are already receiving Social Security benefits, you will be automatically enrolled in Medicare Parts A and B.

Check if your employer coverage is creditable

If you have employer coverage, confirm whether it is "creditable" — meaning it is at least as good as Medicare. This determines whether you can delay Part B without penalty.

List all your current doctors

Compile a list of every doctor, specialist, and hospital you use. You will need this to verify network coverage when comparing plans.

List all your current prescriptions

Write down every medication, dosage, and frequency. This is essential for comparing Part D drug plan formularies.

Research your Medicare options

Understand the difference between Medicare Advantage and Medigap + Part D. Read our Florida Medicare guide or call William for a free consultation.

During Your Initial Enrollment Period (7 months)

Enroll in Medicare Part A (Hospital Insurance)

Most people get Part A free. Enroll at ssa.gov or by calling Social Security at 1-800-772-1213.

Enroll in Medicare Part B (Medical Insurance)

Part B costs $202.90/month in 2026 (standard). Enroll at the same time as Part A unless you have qualifying employer coverage.

Receive your red, white, and blue Medicare card

Your Medicare card will arrive by mail within 3–4 weeks of enrollment. Keep it safe — you will need it for all medical appointments.

Compare Medicare Advantage plans in your ZIP code

Use Medicare.gov or call William to compare every plan available in your area. Verify your doctors and medications are covered.

Compare Medigap plans if choosing Original Medicare

If you choose Original Medicare, compare Medigap Plan G or Plan N rates from multiple carriers. William shops 15+ carriers for the lowest rate.

Enroll in a Part D drug plan

Even if you choose Medicare Advantage with drug coverage, confirm your plan includes Part D. If you choose Medigap, you must enroll in a standalone Part D plan.

After Enrollment

Confirm your coverage start date

Verify when your Medicare and supplemental coverage begins. There should be no gap between your old coverage ending and new coverage starting.

Update your doctors with your new insurance information

Bring your Medicare card and new plan ID card to your next appointment. Confirm your doctors accept your new plan.

Set up your MyMedicare.gov account

Create an account at MyMedicare.gov to track your claims, check your coverage, and manage your Medicare information online.

Schedule your Welcome to Medicare preventive visit

Within the first 12 months of Part B, you are entitled to a free Welcome to Medicare preventive visit. Schedule it with your primary care doctor.

Mark Annual Enrollment Period on your calendar

AEP runs October 15 through December 7 every year. This is when you can switch plans. William will proactively review your plan each fall.

Don't Miss Your Enrollment Window

The Part B late enrollment penalty is 10% per 12-month period you delayed — and it is permanent. The Part D penalty is 1% per month you went without creditable drug coverage. These penalties last for the rest of your life.

Read the full Medicare penalties guide

Frequently Asked Questions

What is the Medicare Initial Enrollment Period?

Your Initial Enrollment Period (IEP) is a 7-month window centered on your 65th birthday month — 3 months before, your birthday month, and 3 months after. This is your primary window to enroll in Medicare Parts A and B.

What documents do I need to enroll in Medicare?

You will need your Social Security number, proof of U.S. citizenship or legal residency, and information about any current health insurance coverage. If you are delaying Part B due to employer coverage, you will need documentation from your employer.

Can I enroll in Medicare online?

Yes. You can enroll in Medicare Parts A and B at ssa.gov/medicare. For Medicare Advantage and Part D plans, you can enroll through Medicare.gov or by calling the carrier directly. William can also handle enrollment on your behalf at no charge.

What if I miss my Medicare enrollment window?

If you miss your Initial Enrollment Period without a qualifying Special Enrollment Period, you will face a permanent 10% Part B penalty for every 12 months you delayed, plus a Part D late enrollment penalty. Contact William immediately to assess your options.

Primary Service Area — County Medicare Guides

Volusia County Medicare Guide 2026Medicare Advantage, Medigap, Part D, and Halifax Health network info for Volusia County.Flagler County Medicare Guide 2026Medicare plans, AdventHealth Palm Coast network, and enrollment help for Flagler County.St. Johns County Medicare Guide 2026Medicare options, Flagler Hospital network, and enrollment guidance for St. Johns County.Duval County Medicare Guide 2026Medicare plans, Baptist Health, Mayo Clinic, and UF Health network info for Jacksonville.Putnam County Medicare Guide 2026Medicare Advantage, Medigap, and HCA Putnam Hospital network info for Palatka seniors.

More Free Medicare Guides

Medicare Scams in FloridaThe 6 most common Medicare fraud schemes targeting Florida seniors — and how to protect yourself.Turning 65 Medicare GuideEnrollment windows, plan types, 2026 costs, and how to avoid lifetime penalties.Medicare After RetirementWhat happens to your coverage when you retire — before or after 65.How to Avoid Medicare PenaltiesThe Part B, Part D, and Medigap penalties — and exactly how to dodge them.Medicare & Social SecurityHow Medicare and Social Security work together, including automatic enrollment rules.Medicare for VeteransHow VA benefits and Medicare coordinate — and when you need both.

Need Help Working Through This Checklist?

William walks Florida seniors through every step — free, no pressure, no obligation.

Call (386) 871-3858 Schedule a Free Medicare Review