Turning 65? Here’s Your Medicare Checklist
If you’re turning 65 soon, it’s time to start planning for Medicare enrollment. Whether you’re retiring or continuing to work, understanding your Medicare options and deadlines is crucial to ensuring you have the right health coverage.
At Covered by Tara, I specialize in helping individuals navigate Medicare enrollment with ease. To help you stay organized and informed, I’ve put together this step-by-step Medicare checklist so you can confidently transition into this next chapter of healthcare coverage.
Medicare Checklist: What to Do Before You Turn 65
Step 1: Learn About Your Medicare Options (6-12 Months Before 65th Birthday)
Medicare consists of different parts, each covering specific healthcare services:
- Medicare Part A (Hospital Insurance) – Covers hospital stays, skilled nursing care, and hospice.
- Medicare Part B (Medical Insurance) – Covers doctor visits, outpatient care, preventive services, and durable medical equipment.
- Medicare Part C (Medicare Advantage) – An all-in-one plan offered by private insurers that includes Part A, Part B, and often Part D (prescription drug coverage).
- Medicare Part D (Prescription Drug Plan) – Covers medications prescribed by your doctor.
- Medicare Supplement (Medigap) – Helps cover out-of-pocket costs like copays, coinsurance, and deductibles for those who choose Original Medicare (Parts A & B).
Pro Tip: If you need extra benefits like dental, vision, hearing, and fitness programs, a Medicare Advantage plan may be a good fit for you.
Step 2: Check Your Medicare Enrollment Period (3-6 Months Before 65th Birthday)
Your Initial Enrollment Period (IEP) lasts seven months:
- Starts: 3 months before your 65th birthday
- Ends: 3 months after your birthday month
If you’re already receiving Social Security benefits, you’ll be automatically enrolled in Medicare Part A & Part B. Otherwise, you’ll need to enroll manually through the Social Security Administration.
Avoid Late Penalties: If you don’t sign up for Part B when first eligible and don’t have qualifying employer coverage, you may face lifetime late enrollment penalties.
Step 3: Decide If You Need Medicare If You’re Still Working
If you’re still working past 65 and have employer-sponsored health insurance, consider:
- Employer plan size – If your company has 20+ employees, you can delay Medicare Part B without penalties.
- Prescription drug coverage – Ensure your employer’s plan is creditable (comparable to Medicare Part D).
- Cost comparison – Compare employer plan costs vs. Medicare to determine the most affordable option.
Talk to your HR department to see how Medicare works with your employer coverage.
Step 4: Enroll in Medicare (3 Months Before Your 65th Birthday)
Once you decide on your Medicare coverage, it’s time to enroll! You can sign up for Medicare Part A and/or Part B through:
- Social Security website – ssa.gov/medicare
- Local Social Security office – Call 1-800-772-1213
- By phone – Apply over the phone with Social Security
Pro Tip: If you want a Medicare Advantage or Part D plan, you’ll need to enroll in Parts A & B first.
Step 5: Compare Medicare Plan Options (1-3 Months Before 65th Birthday)
Once you have Original Medicare (Parts A & B), you can choose between:
- Staying with Original Medicare and adding a Medigap plan + Part D
- Choosing a Medicare Advantage plan (Part C), which includes medical and drug coverage
What’s the difference?
| Medicare Option | Best For | Includes | Extra Benefits |
| Original Medicare (Part A & B) + Medigap | Those wanting nationwide provider access and help with out-of-pocket costs | Hospital & medical services | Need to add a Part D plan for drug coverage |
| Medicare Advantage (Part C) | Those who want all-in-one coverage, including extras | Hospital, medical, and often drug coverage | Many plans offer dental, vision, hearing, and fitness programs |
Need help comparing plans? I can provide free, expert guidance to help you find the best Medicare Advantage, Part D, or Medigap plan for your needs.
Step 6: Enroll in a Medicare Advantage, Medigap, or Part D Plan
Once you choose your coverage, you can enroll in a Medicare plan:
- Medicare Advantage (Part C) – Enroll through a private insurer
- Medicare Supplement (Medigap) – Enroll through a private insurance carrier
- Medicare Part D (Prescription Drug Plan) – Enroll through an approved insurance provider
Important Deadlines:
• Medigap Open Enrollment: 6-month period after enrolling in Part B (best time to get a Medigap plan with no medical underwriting).
• Medicare Advantage & Part D Enrollment: Must enroll during your Initial Enrollment Period or Medicare’s Annual Enrollment Period (Oct 15 – Dec 7).
Step 7: Review Your Medicare Plan Annually
Once you’re enrolled, review your Medicare coverage each year during the Medicare Annual Enrollment Period (AEP) (Oct 15 – Dec 7).
Ask yourself:
- Are my doctors and hospitals still covered?
- Are my prescriptions still on my plan’s drug list?
- Does my plan still fit my budget and health needs?
If your needs change, you can switch Medicare Advantage or Part D plans during AEP.
Pro Tip: Medicare Advantage plans change annually—review your benefits each year to ensure you’re getting the best coverage.
Need Medicare Help? Covered by Tara Offers Free Assistance!
Navigating Medicare enrollment can be overwhelming, but you don’t have to do it alone. As a licensed Medicare specialist, I offer free, personalized guidance to help you:
- Compare Medicare Advantage vs. Medigap options
- Find a Part D drug plan that covers your prescriptions
- Avoid late enrollment penalties
- Choose a plan that fits your healthcare needs and budget
Call/Text: 386-229-5885
Visit: CoveredByTara.com
Serving Medicare beneficiaries in Florida
Don’t wait until the last minute—get expert Medicare advice today!
