Turning 65 comes with one big to-do: Medicare. The good news is that it follows a predictable timeline. Here is what to do and when, so nothing catches you off guard.

Around your 65th birthday — your Initial Enrollment Period

You get a 7-month window around your 65th birthday (the months before, the month of, and the months after) to enroll in Medicare. Signing up in this window helps you avoid gaps and potential late penalties.

Step 1 — Decide on Parts A and B

Most people take Part A (usually premium-free) at 65. Whether to take Part B right away can depend on your situation, for example, if you are still working with employer coverage (more on that below).

Step 2 — Still working past 65?

If you have qualifying employer coverage, you may be able to delay Part B without penalty and enroll later through a Special Enrollment Period. The rules matter here, so it is worth confirming yours before you decide.

Step 3 — Choose how to round out your coverage

This is the key decision: Original Medicare + Medigap + Part D, or a Medicare Advantage plan. Your doctors, medications, and budget guide the choice. If you would like a refresher on how the parts fit together, our guide to Medicare walks through each one.

Step 4 — Add prescription drug coverage

If you go the Original Medicare route, add a standalone Part D plan matched to your medications. Many Medicare Advantage plans include it.

Step 5 — Review each year

Plans can change year to year, so it is smart to review your coverage during the Annual Enrollment Period (October 15 – December 7).

Common mistakes to avoid

• Missing your enrollment window and facing a gap or penalty.
• Picking a plan without checking your doctors and medications.
• Assuming Original Medicare covers dental, vision, or long-term care (it generally does not).

How we help

We will map your exact timeline, explain your options in plain language, and help you choose with confidence, with no pressure. Call us at 908-400-6735 or reach out anytime.

Frequently asked questions