Start with a clear Medicare timeline
Turning 65 brings an important health insurance decision—and usually a mailbox full of information. You do not have to sort through everything at once. Start with your enrollment dates, understand how Medicare fits with your current insurance, and then compare coverage around your doctors, prescriptions, and budget.
This guide walks you through the process, whether you are considering Original Medicare with a Medicare Supplement and prescription drug plan, or a Medicare Advantage plan.
1. Put your Medicare enrollment window on the calendar
For most people, the Initial Enrollment Period lasts seven months: the three months before your 65th birthday month, your birthday month, and the three months after it. If you want Part B to begin during your birthday month, generally enroll during the three months beforehand. Enrolling during your birthday month or the following three months generally starts Part B the next month. A birthday on the first of the month shifts the timing, so check your dates carefully.
Your first task: write down your birthday month, your expected Medicare start date, and the date your current insurance will end. Plan ahead so those dates line up.
2. Check your current coverage before deciding when to enroll
Still working at 65, or covered through a spouse who is working? You may be able to delay Part B while covered by a group health plan based on current employment. Ask the employer benefits administrator how the coverage works with Medicare. With fewer than 20 employees, Medicare generally pays first, and delaying enrollment can leave gaps.
COBRA, retiree insurance, and Marketplace coverage do not provide the same Part B enrollment protection as coverage based on current employment. For qualifying job-based coverage, the Part B Special Enrollment Period generally ends eight months after employment or coverage ends, whichever happens first. Arrange coverage before your employer plan ends; drug-plan deadlines are different.
Have a Health Savings Account? Once Medicare coverage begins, you cannot contribute to an HSA. Applying after 65 can make premium-free Part A retroactive by up to six months, but not before you first became eligible. Review both your own and employer contributions before applying for Medicare or Social Security.
3. Confirm how you will get Parts A and B
Original Medicare has two main parts:
• Part A helps cover inpatient hospital care, qualifying skilled nursing facility care, hospice, and some home health care.
• Part B helps cover doctor visits, outpatient services, preventive care, and durable medical equipment.
Most people qualify for premium-free Part A through their own or a spouse’s work history. Part B has a monthly premium.
If you receive Social Security benefits at least four months before turning 65, you generally get Parts A and B automatically. Check your Medicare enrollment packet and effective dates.
If you are not enrolled automatically, apply through Social Security. You can apply for Medicare without starting Social Security retirement benefits. Sonon Insurance can help you understand the next steps, but your application for Parts A and B goes through Social Security.
4. Understand your two main coverage paths
Once you know when Medicare will begin, consider how you want to receive your coverage.
Path one: Original Medicare + Medigap + Part D
With this approach, you keep Parts A and B and can add:
• Medicare Supplement Insurance, also called Medigap, to help pay certain deductibles, copayments, and coinsurance for Medicare-covered care. The benefits depend on the policy you choose.
• A separate Part D prescription drug plan, because new Medigap policies do not include prescription drug coverage.
• Optional dental and vision insurance, for needs such as routine dental care, eye exams for glasses, and eyewear, which Original Medicare generally does not cover. Medigap generally does not cover these either. Review separate policies for networks, waiting periods, and benefit limits.
Path two: Medicare Advantage, also called Part C
A Medicare Advantage plan is a private insurer’s alternative way to receive your Medicare benefits. You must have Parts A and B and generally continue paying your Part B premium. Most plans include Part D, and many offer dental, vision, or hearing benefits. Check the specific plan’s benefits and restrictions.
A $0 Medicare Advantage premium does not mean all care is free. You cannot use Medigap to pay Medicare Advantage cost sharing.
5. Protect your Medigap enrollment opportunity
Your federal Medigap Open Enrollment Period lasts six months, beginning the first month you are both 65 or older and enrolled in Part B. During that window, insurers cannot deny a policy or charge more because of your health.
Afterward, buying a policy may require medical underwriting unless a guaranteed issue right or state protection applies. Do not assume you can switch from Medicare Advantage to Medigap later with automatic acceptance. Discuss that possibility before making your first coverage choice.
6. Include prescription coverage in your decision
Even if you take no prescriptions today, consider drug coverage when you first become eligible. Going 63 consecutive days or more without Part D or other creditable prescription coverage after your Initial Enrollment Period can trigger a late enrollment penalty. Keep any creditable coverage notice from your employer.
For every drug plan you compare, check your exact medication name, strength, quantity, and pharmacy. Review the formulary—the plan’s covered drug list—and any prior authorization, quantity limits, or step therapy requirements. Compare total estimated yearly costs, including premiums and what you pay at the pharmacy. If choosing Medicare Advantage, confirm whether drug coverage is included before adding anything separately.
7. Gather what you need before shopping
A little preparation makes a plan comparison more useful. Have these details ready:
• Your ZIP code and county.
• Your desired coverage start date and current insurance end date.
• Your doctors, specialists, preferred hospitals, and pharmacies.
• Your prescriptions, including strength and how often you refill them.
• Your monthly budget and priorities for dental, vision, travel, and ongoing care.
• Your Medicare Part A and Part B effective dates, once confirmed.
You can start learning and comparing before your Medicare card arrives. Before submitting an enrollment, confirm the applicable enrollment period and effective date. Medicare Advantage requires both A and B; a standalone Part D plan requires A or B. Joining a plan.
Do not cancel existing insurance until your new coverage and start dates are confirmed. Compare plans for the year your coverage will begin, especially if your birthday falls near the end of the year.
Ready for your next step? Start with Sonon Insurance
You do not have to choose a plan before asking for help. Start with your dates and your list of doctors and prescriptions, and we can work through the options together.
Explore Medicare plans online
Prefer to explore online? Visit our Medicare page to start shopping plans.
Book a Medicare meeting with Justin Sonon
Want personal guidance? Discuss your timeline and compare coverage paths with Justin Sonon.
Request a Medicare quote
Want help with pricing? Tell us when you turn 65, where you live, and whether you are interested in Medigap, Medicare Advantage, or help understanding both. Your next step can be simple: gather your information and choose the way you would like to get started.
About this Medicare information
Sonon Insurance is not affiliated with or endorsed by Medicare or the federal government. We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Assistance Program to get information on all of your options.
Compare your two Medicare coverage paths
Review these differences alongside your doctors, prescriptions, budget, and travel needs.
| What to compare | Original Medicare with Medigap and Part D | Medicare Advantage |
|---|---|---|
| Doctors and hospitals | Generally any provider nationwide that accepts Medicare; Medicare SELECT policies have network rules | Networks and out-of-network costs vary by plan |
| Monthly premiums | Part B, plus separate Medigap and Part D premiums | Part B, plus any plan premium; some plans have a $0 plan premium |
| Costs when you receive care | Medigap helps pay covered medical cost sharing, depending on the policy | Plan-specific deductibles, copayments, and coinsurance |
| Medical spending protection | Original Medicare alone has no annual out-of-pocket limit; Medigap helps with covered costs | Annual limit for covered Part A and B services; premiums and drug costs are separate |
| Care rules | Usually no specialist referral requirement | Referrals and prior authorization may apply |
Helpful resources
Coverage, eligibility, and plan terms vary by carrier and state. This article is general information, not a promise of coverage or individualized financial advice.
