Retirement planning isn’t only about money. It’s also about protecting your health. You’ve worked hard for this next chapter of your life, and you deserve to enjoy it without worrying about surprise medical costs or confusing insurance rules. That’s where this checklist comes in. It covers what you need to know and do to feel confident about your healthcare plan as you step into retirement.

Let’s break it down.

Understand What Medicare Actually Covers

Medicare is one of the most important parts of your retirement plan, but many people don’t fully understand it. They assume it covers everything, but that’s not the case.

Medicare is made up of several parts:

• Part A includes coverage for hospital stays and certain skilled nursing services. In most cases, there’s no monthly premium required.
• Part B covers doctor visits, outpatient care, lab work, and some preventive services. You usually pay a monthly premium for this.
• Part C, also called Medicare Advantage, is an all-in-one alternative. It combines Parts A and B and often includes extras like dental and vision. These are offered by private companies.
• Part D helps cover prescription drug costs. Plans vary in price and coverage.

You still have out-of-pocket costs with Medicare. That includes deductibles, coinsurance, and sometimes extra charges from providers. Understanding what each part covers helps you avoid surprises later.

If all of this sounds like a lot, that’s because it is. Luckily, there are tools to help you figure it out. One great place to start is here: https://medicareonvideo.com/

Medicare on Video is a free resource that explains the different parts of Medicare in simple terms. You can even get help comparing plans and enrolling.

Pick the Right Time to Enroll

When it comes to Medicare, signing up at the right time is important. Your first opportunity to enroll is called the Initial Enrollment Period. This happens around your 65th birthday and lasts for seven months total, starting three months before your birthday month and ending three months after it.

If you don’t sign up during that time, you could face late enrollment penalties. These penalties stick with you for life in some cases. That’s why it’s important to mark your calendar and be ready ahead of time.

If you’re still working and have coverage through your job, different rules may apply. You might be able to delay some parts of Medicare without a penalty. But you’ll want to check the details carefully. Don’t assume—ask questions and get clear answers before deciding to wait.

Decide Between Original Medicare and Medicare Advantage

Once you’re enrolled, you’ll need to choose between Original Medicare and a Medicare Advantage plan. Both have pros and cons.

Original Medicare gives you the freedom to see most doctors and specialists across the country. But it also means more out-of-pocket costs unless you add a Medigap (Medicare Supplement) plan. These plans help cover the costs that Original Medicare doesn’t pay.

Medicare Advantage plans are more like traditional health insurance. They often include drug coverage, dental, vision, and hearing. But they usually have a network of doctors, so you may need referrals or stay in-network for care.

Which one is better? It depends on your preferences, budget, and health needs. Take time to compare what’s available in your area. Look at premiums, coverage, and provider networks before making a choice.

Think About Prescription Drug Coverage

Even if you’re not on regular medications now, that could change. It’s smart to have a plan in place so you’re not caught off guard.

Medicare Part D plans cover prescription drugs, but they’re not all the same. Each plan has its own list of covered drugs, also known as a formulary. It’s important to check this list before enrolling. Make sure your medications are covered and see how much they’ll cost under the plan.

If you skip this step and go without drug coverage, you might pay a late enrollment penalty down the road. That’s why it’s a good idea to choose a plan when you’re first eligible, even if your needs are minimal right now.

Don’t Forget Dental, Vision, and Hearing

One big surprise for many retirees is that Medicare doesn’t cover routine dental, vision, or hearing care. That includes things like eye exams, hearing aids, and dentures.

These services are important, especially as we age. Poor dental or vision health can lead to bigger medical issues. That’s why it’s worth looking into separate coverage or a Medicare Advantage plan that includes these benefits.

You can also buy stand-alone dental, vision, and hearing plans. These vary by provider and location, so compare coverage carefully. The cost is usually manageable and could save you more in the long run.

Review Your Plan Every Year

Your health needs change over time—and so do Medicare plans. That’s why it’s important to review your coverage every year.

The Annual Enrollment Period runs from October to December. During this time, you can:

• Switch from Original Medicare to Medicare Advantage
• Change Medicare Advantage plans
• Join, drop, or switch Part D drug plans

Even if you’re happy with your current plan, take time to review it. Look for changes in premiums, drug formularies, or provider networks. You might find a better plan that fits your current needs.

Prepare Legal and Emergency Documents

This part of the checklist often gets skipped, but it’s just as important.

Make sure you have the following documents:

• Healthcare power of attorney – This allows someone you trust to make medical decisions if you can’t.
• Living will or advance directive – This outlines your wishes for end-of-life care.
• Medication list – Keep an up-to-date list of what you take and why.
• Emergency contacts and provider info – Include your doctors, specialists, pharmacy, and preferred hospital.

Store these documents in a safe, easy-to-access place. Share copies with a family member or trusted friend. It can make a big difference during an emergency.

Taking care of your health in retirement doesn’t have to be overwhelming. When you break it down into clear steps, it becomes much easier to manage. Use this checklist as a guide and revisit it each year. Keep asking questions and looking for simple, reliable resources when you need support.

Planning ahead gives you peace of mind. It helps you stay focused on what really matters—enjoying this new stage of life.